Pitchbook and Carta have both reported that investment levels are up in 2026, but the number of deals is down, so in simple terms…more money into fewer startups.

A handful of AI companies are raising a hundred million at seed. Most other founders are building deep IP on solid fundamentals and getting overlooked, and that’s exactly where the best angels are hunting.

Founders, if you’re sitting on a list of 400 investors someone told you to warm up, pay close attention!

Cheryl lays out a three-stage sequence that starts with the people who already know you. She also tells a story about a $5,000 angel and a red-eye flight that I haven’t stopped thinking about. The short version is that small checks bring more than money, and founders who figure that out early raise faster.

“There’s real money out there hiding in small checks.”
Cheryl Kellond

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The research

• The pool is huge and mostly idle. The SEC’s latest review of the accredited investor definition estimated 24.3 million US households, or 18.5%, qualified in 2022. That’s up from 1.8% in 1983. (SEC staff report, December 2023)

• Angels are carrying seed. Angels put $17.9B into 55,346 ventures in 2024, and 59% of those deals were seed or earlier. Over the same period, VC seed deal count fell 16%. (UNH Center for Venture Research, The Angel Market in 2024)

• VC money is piling into one corner. AI took a record 82.7% of US venture deal value through Q3 2026. Total deal value reached $515.8B, already about 44% above the previous annual record. (PitchBook-NVCA Venture Monitor, Q3 2026)

• Geography is concentrating too. 55% of new VC fund commitments in 2025 went to Bay Area firms. The Bay Area and New York now hold 68.9% of US venture assets under management. (PitchBook Analyst Note, March 2026)

• Small funds punch above their weight. In recent vintages, VC funds with $1M to $10M in commitments have tended to beat $100M+ funds on net TVPI and IRR at the top percentiles. Even so, 57% of cash raised by new funds in 2025 went to $100M+ vehicles. (Carta, VC Fund Performance reports, 2025 and Q1 2026)

The playbook

1. Start with the people who already know you. Cheryl calls stage one friends and family, then admits she hates the phrase because plenty of founders don’t have relatives with deep pockets. What she means is the ecosystem around your expertise: former colleagues, potential customers, people in your field who’ve watched you work. They bet first because they know you. The failure mode is skipping this group out of awkwardness, then spending six months pitching strangers who have no reason to trust you yet.

2. Earn one professional signal. Stage two is an angel group, a syndicate lead or a first-time fund manager who does real diligence. On Play Money, a deal doesn’t reach the wider network until a professional investor has checked the cap table, the incorporation and the story. That signal is what lets strangers say yes in stage three. Founders get this wrong when they treat diligence as a hurdle to dodge, when it’s actually what makes the rest of the raise easier.

3. Fill the room before you open the door. Cheryl’s test is simple. Pull $30K to $50K from your own network before you ask anyone else. Fifteen people who already believe in you will do more selling than your deck. The failure mode is launching wide on day one and watching interested strangers stall because nobody has gone first.

4. Send the update before you need the money. Cheryl would rather read a string of monthly updates than open your data room. Updates show your pace of learning: the hypothesis, the test, what changed. Start now, even if your list is twenty people. Where founders go wrong is building a forty-tab financial model for a business that doesn’t have customers yet.

5. Put your small checks to work. Play Money gives founders the contact details of every angel in their SPV, and Cheryl says 95% of their founders include them in investor updates. Ask those people for intros, hires and customers. The failure mode is buying the myth that thirty angels means thirty board meetings, then never asking any of them for help.

Sources:

• SEC staff report on the accredited investor definition (Cozen O’Connor summary)

• UNH Center for Venture Research, The Angel Market in 2024

• SiliconANGLE on the Q3 2026 PitchBook-NVCA Venture Monitor

• PitchBook Analyst Note: Differentiating VC Returns by Series Across US Regions, March 2026

• Carta: 1M–10M VC funds tend to outperform $100M+ funds

• Carta: VC Fund Performance Q1 2026

How to fill your first round with the people who already back you, and keep your cap table clean.

TL;DR

• This piece is for founders who want to run their angel round through an SPV, whether you’re planning it or already raising.

• Rounds today are smaller and slower: 35% of pre-seed rounds now come in under $250K, and seed to Series A takes about 20 months.

• Your fastest money is people who already know you, from ex-bosses to customers to friends, you just need to ask.

• Play Money pools them into one SPV, so you get one line on your cap table, and it’s free for founders.

• Apply, then send one link to 30 people.

• → Apply at Play Money

If you’re planning your angel round, or you’re already in it and the checks are piling up, this is written for you.

I’m the fractional Head of Growth at Play Money, a platform built for exactly this kind of round. I have been working with Cheryl Kellond, the legendary Founder since January on the Angels Decoded podcast, which has been a blast. We were bouncing around some ideas for growth and then jumped in with Cheryl, and my eyes have been opened to the opportunity on this platform

As a first-time founder, the people most likely to back you early are the ones who already know you, and asking them shouldn’t be that hard, as long as you are organized and share all the important information they need to make an informed decision.

And if you don’t have a network, that’s ok too. Driving engagement on your angel round can happen in a few ways and the best part of Play Money is that it combines all of those. I get into that further down.

"The founders who close fastest get their own people in first, and I don't mean the traditional friends and family. I mean colleagues and classmates, the people who know your professional prowess and who make up the network and connections you need to build, sell and hire as you grow. Those early investors become social proof for the ones who don't know you yet, and Play Money handles the cat herding, so you can get back to building your business instead of chasing wires." Cheryl Kellond

Why angel rounds feel harder than they should

I did some research to get my head into the data and help paint a broad picture.

Fewer founders are getting funded. Last year, U.S. startups on Carta raised roughly the same pre-seed money as the year before, across 13% fewer SAFEs and notes. Same money, fewer winners.

The checks got smaller. In Q4 2025, 35% of pre-seed rounds on Carta came in under $250K. Small rounds mean more investors, more SAFEs, and more late-night email threads.

The road got longer. The median gap between seed and Series A on Carta hit 616 days in Q2 2025. Whatever you raise now has to last well past the 18 months you have modelled.

If your calendar is full of “love it, keep us posted” meetings, that’s the market. But you need to keep those people warm and engaged. In fact, you need to tell those people about you before you even think about a raise.

Start with the people who already believe in you.

The former boss who said, “let me know when you raise.” The customer who tells everyone about you. The college friend who’s done well and has never written an angel check, because nobody asked them.

Founders skip those calls for three reasons. Asking people you care about for money feels awkward. Wrangling twenty small checks sounds like a part-time job. I see VCs warn founders about the messy cap table that scares off a Series A lead.

For whatever reason, VCs seem to have an issue with Angels. They will discredit their value, make out that they cause problems, and that they need to be managed regularly.

It is all posturing bullshit, you just need to set up the angel properly. Angels will add value beyond most VCs!

Play Money takes care of the workflow. The platform pools your angels into a single SPV, a “Special Purpose Vehicle” that invests in your company as one entity. One line on your cap table, one signature, one set of documents.

They also build you an interactive deal memo that does the pitching for you, so you send one link instead of thirty decks. Low minimums turn curious friends into first-time angels, closes are rolling, and it’s free for founders. Angels cover the fees, with 0% carry.

→ Apply at Play Money

Which SPV fits your round?

Your People, Your Round. Friends, family, customers and ex-colleagues, with great combined potential between them.

Backed by the Big Kids. A VC is leading, and you want to top off with the people who believed in you first.

Bring Your Own Syndicate. Angels are already circling, and you want them in one clean line.

Set up your SPV this week.

1. List 30 people who’ve ever said “let me know when you raise.”

2. Pick your number and your close date.

3. Apply to Play Money and get your deal memo built.

4. Send one link to all 30.

5. Hold the close date, even when it feels uncomfortable.

The people who already believe in you deserve a simple way to say yes. Get organized and ask the question.

→ Apply at Play Money

Not sure which SPV fits your round? Reply to this email, and the team can help.

Sources:

• Carta: State of Pre-Seed 2025 in review

• Kruze Consulting: Pre-seed funding guide (Carta 2025 figures)

• mean.ceo: Pre-seed stats roundup (Carta Q4 2025)

• mean.ceo: Series A stats roundup (Carta 616 days)

Angus Dobbie watched this happen from inside corporate recruiting for fifteen years, then lost his own footing twice, once in the 2008 crash and once launching his own product this year. This week he’s on Startups Decoded to talk about JobPass, the system he built to turn a job hunt into something you can actually run.

My take: a job search and an early-stage company are the same game in different clothes. You’re on your own, nobody is managing you, everything takes longer than planned, and the front door is jammed with people doing exactly what you’re doing.

Angus lands on structure, a handful of pipelines you keep moving, and relationships you build long before you need them.

I am an advisor for JobPass. Proud to be on the team!

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The research

• The front door got twice as crowded. Greenhouse data shows applications per opening more than doubled between 2022 and 2025, climbing from an average of 116 to 244. That figure comes from its Hire Standard report, published March 2026, covering more than 640 million applications across over 6,000 companies.

• Fewer people are reading them. Over the same period, Greenhouse found the number of recruiters fell 56%, which is exactly the trade Angus describes: companies bought AI screening and cut the humans to pay for it.

• The AI interview is now the first gate, and candidates hate it. Greenhouse reports around 63% of U.S. job seekers have been interviewed by AI. In its 2026 Candidate AI Interview Report, 38% said they’d already pulled out of a process because of one, and among those who finished an AI interview, 51% never got an outcome.

• Referrals are a different pool entirely. CareerPlug’s review of more than 10 million applications from 60,000+ small businesses found referrals were just 2% of applicants but 11% of all hires in 2024. Job boards, by contrast, produced 61% of applications and only 42% of hires, and referred candidates were ten times more likely to be placed.

• Plan for the long version. BLS data shows 1.8 million people had been jobless for 27 weeks or more in July 2026, or 25.5% of everyone unemployed. A year earlier, in March 2025, that share sat at 21.3%. Angus’s point stands: most people plan for weeks when they should plan for months.

The playbook

1. Split your work into separate pipelines. Angus runs a job search as four pipelines: target companies, applications, networking, and recruiters. That’s target accounts, outbound, warm network, and connectors like investors and advisors who see deal flow. Each pipeline gets its own weekly activity target, because momentum in one hides neglect in another. The failure mode is The Single Pipe, where every hope rides on one channel, usually cold outbound, and a bad month there feels like a bad company.

2. Every name gets a next action. Angus’s first move in his own search was syncing LinkedIn into a CRM, and he woke up with 10,000 people in his pipeline. JobPass won’t let you add anyone without a task attached, and you should run the same rule. If a contact doesn’t have a next step and a date, it doesn’t belong in your system yet. The failure mode is The Dumping Ground, a CRM so full of names that nothing in it moves.

3. Find the side door before the front door. Angus is blunt about why the order matters: once you’ve gone through the system and been rejected, getting back into the process is far harder. The failure mode is The Burned Door, where founders spend their one shot on the cold channel and then go looking for an intro after the answer is already no.

4. Network with no ask attached. Angus has two habits worth copying. Text roulette means scrolling through your messages about twenty times, landing on someone you haven’t spoken to in ages, and simply checking in. Dealer’s choice means sending an article or idea to someone who’d care, with nothing requested. The failure mode is The Transactional Ask, where every outreach is a pitch, and people learn to brace when your name appears.

5. Plan for the long version. Angus sees the same pattern constantly: someone lands a second-round interview and stops everything else, waiting for it to come through. Founders do this with one hot deal or one interested investor. Keep every pipeline moving until the money is in the bank or the contract is signed, and expect a flat spot after any big milestone, including launch. The failure mode is The Hot Lead Freeze.

“I wrote this up for myself. It says, I am not special.”
Angus Dobbie, on what he wishes he’d told himself before launch

When I started my first company, I thought an accelerator was about the curriculum. The workshops, the frameworks, the demo day. Those things help, but the founders I watched pull ahead got something bigger out of it. They got access.

An investor who took a second meeting, an operator who’d already solved their exact problem, a peer six months ahead who told them which mistakes to skip. Accelerators at their best compress years of relationship-building into a few months, and that’s why the good ones change the trajectory of a company.

That matters if you’re Maya, seven months of runway, trying to work out where your next forty hours go. The right relationships can save you a year of guessing, and the fastest way to build them is to be in rooms designed for exactly that. I’ll be hosting the main stage at one of those rooms this week, and I’ll tell you about it at the end. First, the data on why connection drives growth, a playbook for making the most of a day like this, and a worksheet so you walk in with a plan.

The research

• Connected founders grow faster. Early-stage startups with stronger local networks see their revenue grow twice as fast as those with weaker ones. Startup Genome’s benchmark for a well-connected founder is quality relationships with about 25 other founders, eight investors, and 10 experts. (Startup Genome)

• Accelerators move the numbers that matter. Research on a corporate accelerator found that attending was positively associated with survival, employee growth, and funds raised. (Nesta)

• Investor relationships compound. In a study following a full cohort of 105 startups through an international accelerator, those that built more investor ties during the program survived and raised capital at a higher rate. (ANDE)

• Mentorship turns into milestones. The same study found startups that took part in more mentorship events were more likely to ship a prototype and generate their first revenue during the program. (ANDE)

• Access matters more than ever. Pre-seed capital is concentrating, with similar sums going into noticeably fewer deals and average instrument size hitting a record $276,000 in Q2 2026. When investors are writing bigger checks into fewer companies, being known to them early is a real advantage. (Carta)

The playbook: how to make the most of a one-day room

1. Pick your five before you walk in. Go through the attendee list and choose five people who could shape your next 90 days: two investors, one accelerator, one operator who has solved your current problem, and one founder a year ahead of you. Everyone else is a bonus. Founders often try to meet everyone, then leave with a stack of contacts and no clear next step.

2. Build a 60-second version with one ask. You’ll get about a minute with most people, so spend it on the problem, your proof, and one specific request. People love helping founders who make it easy to help them. The common slip is cramming in the product, the vision, the team and the market, until the listener isn’t sure what you need.

3. Book your meetings before the day. If the event offers scheduled one-on-ones or matchmaking, use them and lock your slots early. Spontaneous conversations are great, and a few booked meetings guarantee your most important ones actually happen. Founders who wait for the right person to wander past often miss them.

4. Get to know the accelerators. Every accelerator has its own strengths, whether that’s a sector focus, an investor network, or deep operator support. Ask what their recent founders gained most from the program and what kind of company thrives with them. The goal is fit, and the best programs welcome those questions.

5. Follow up within 48 hours with something useful. Send a short note that references your conversation and offers something back, a contact, an article, a data point. Energy is highest right after an event, and a thoughtful second touch is what turns a good chat into a relationship. A generic “great to meet you” tends to get lost.

“Your next investor, cofounder or first big customer is usually one good introduction away.”

AcceleratorCON 2026: Where I’ll be on October 23

Full transparency: this is a paid partnership, and Startups Decoded is an official AcceleratorCON Community Partner. I’m also hosting the main stage all day, which I’m very much looking forward to.

AcceleratorCON brings founders, investors, accelerators, operators, and ecosystem leaders together in New York City for one high-impact day built around intentional connection.

On the day, you’ll find…

• live 60-second founder pitches

• the Draft Experience

• startup-investor matchmaking

• scheduled one-on-ones

• Speed Networking

• Meeting Hub

• sessions on AI, robotics, biotech and physical AI

• investor and accelerator programming

• The University Pavilion

• AcceleratorCON Championship Pitch

• and an Investor Edition of Pop the Balloon

Participating accelerators and investors include Build in Tulsa, Morgan Stanley, Harvard Business School Alumni Angels of NY, Global Entrepreneurship Network, New York Ventures, The Fintech Innovation Lab at Accenture, Entrepreneurs Roundtable Accelerator, the Center for Accelerating Financial Equity (CAFE), Harvard, Stanford, Cornell, CUNY, the University at Buffalo, the Novella Center for Entrepreneurship and more.

For founders, it’s a chance to get discovered by the people who can help you grow. For investors, it’s curated deal flow and more intentional meetings. For accelerators, it’s a room full of founders already building.

Come say hi between sessions. I’ll be the Australian with the microphone.

He also spent that accelerator driving between a NICU and a pitch room, waking at 3am and crying in the hallway, then calling all of it commitment. The company ran out of money, his marriage ended, and for years he assumed the product was the problem. This week he told me the product was fine. The founder running it was running on empty.

That landed hard, because mine was bad during my startup too. I clocked it, did nothing, pushed through, then crashed after the exit and spent a long time rebuilding. If you’re seven months from zero and treating sleep like a line item you can cut, this episode is for you. James is relaunching WeMontage with the same product and a very different operator, and his playbook for that rebuild is the most practical thing I’ve heard on founder mental health in a while.

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The research

• Burnout is the default. In Sifted’s 2025 survey of 138 founders, 54% reported burnout in the past 12 months and 46% described their mental health as bad or very bad. (Sifted, 2025)

• Almost nobody escapes it, and investors mostly look away. Only 6% of those founders reported no mental health issues at all, and 56% said they received no help from investors, while just 3.6% said they got a lot. (Sifted, 2025)

• Boundaries change the numbers. Among founders who held work-life boundaries, 45% reported low burnout, compared with 6% of founders who couldn’t hold them. (Lehigh University, Nasdaq Entrepreneurial Center and TU Dortmund, published in Fortune, September 2025)

• Founders don’t know help exists. In a survey of 227 entrepreneurs across 46 countries, 87.7% reported at least one mental health issue, with anxiety top at 50.2%, yet only 18.5% knew of resources built for founders. (Founder Reports)

• Recovery is the first thing founders cut. In the same Sifted survey, 49% said their workload had increased over the past year, and 47% said their exercise routines had slipped. (Sifted, 2025)

The playbook

1. Check your tank before you make the call. James now tells his daughter upfront when he’s exhausted and short on patience, before she asks for homework help. Do the same with your co-founder and your team, and push any big decision made after a 2am wake-up to the next morning. The failure mode is treating exhaustion as a personality trait, then making hiring, pricing and fundraising calls from a nervous system that’s already in the red.

“You can’t go hard in the paint all the time.”
James Oliver Jr.

2. Book fifteen minutes and protect it. James has fifteen minutes of meditation on his calendar every weekday, plus a morning walk with his dog. Pick one recovery block, put it in the calendar like an investor meeting, and keep it small enough that you can’t talk yourself out of it. Founders usually get this wrong by going all in on a new routine, missing two days, then quitting out of guilt. James misses days too. He just doesn’t beat himself up about it.

3. Audit who’s on your cap table. James was blunt about this: not all money is good money, and an investor demanding seven-day weeks will make your life miserable. Before your next raise, write down which investors you could tell you’re struggling without it costing you. If the answer is none, that’s information. The failure mode is taking money from whoever says yes first, when tools like Claude now let a non-technical founder like James rebuild a prototype in days.

4. Separate attention from traction. Three Today Show appearances, Good Morning America and a CNBC pitch show didn’t save WeMontage, because press doesn’t equal cash flow. James would rather you get every customer to tell ten friends. Look at last month’s calendar and mark which hours drove revenue and which drove applause. Founders usually get this wrong by counting a big feature as progress, then feeling crushed when the sales don’t follow.

5. Get one founder on your side before you need them. James runs Founder Exhale walks in eleven or twelve cities, sixty minutes with other founders, no pitches and no agenda. Find one peer who’s building too and book a standing walk or call. The failure mode is waiting until you’re already in a flat spot, when getting yourself out the door is hardest.

Nobody made me leave Tasmania

But living in Tasmania made me walk toward hard things.

When you live there, you either bunker down and live the same life your parents did, or you leave and get made to feel like you’re abandoning your roots. People there are proud, loyal, and humble. They live good lives. It’s famous for breathtaking landscapes, whiskey, wine, cherries, apples, seafood, art, creative culture, and more recently the MONA museum.

MONA embodies the true spirit of Tasmania. Built by David Walsh, a local who used his math skills to build a fortune as a professional gambler. MONA is his personal art collection, and it’s Australia’s largest private museum. David describes it as a “subversive adult Disneyland.” Tasmania is full of artists of all kinds, and it runs through the full gamut of the local culture and the lifestyle.

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Honest reflections on my origin

When I tell my origin story, I frame it as a journey, an escape, a founder-origin arc. Truth is, that story flatters me. The real version is stranger. No one forced any of it. I kept walking toward the hard thing, on purpose, every time.

As founders, we love the word adversity. It does a lot of heavy lifting in our story. It implies the world came for you and you held strong. Sometimes that’s real, but often it’s just a word we use to make our story sound more grandiose. Startups are a legit challenge, but founders rarely face true adversity. Ask anybody who has lived through adversity, then check yourself.

What I did was different. I chose friction, and did it every time. My mom still worries that I keep choosing an untraveled path, and I still can’t explain why, but I relish it.

I left Tasmania at nineteen and went on adventure after adventure. I didn’t settle down, as I wanted more. More experiences, new people, new places. I did university in a tiny town called Lismore, landed my first job in Noosa, did time with Nike in Melbourne, then decided to move to London. All before turning 25. I left London for Sydney, worked at a big startup, then took the leap and started my first business at 31.

Define chaos… new country, new startup, new baby.

My first startup client was in London, my second in New York. I spent more time on long-haul flights than any person should. I moved my family across the world when my daughter was four months old. Bootstrapping, living on whatever money we could make. None of that was done to me. I self-selected into every hard version of the room. I love New York City, but it had zero reason to give a shit about who I was. I had to create everything, from nothing.

There’s a word for that. Not adversity, it’s actually two words: voluntary difficulty. The distinction matters, because the research on real adversity is a lot more uncomfortable than the pitch-deck version we have seen.

The honest finding is an arch-shape. Some hardship in life (the peak) correlates with more resilience and better wellbeing than either a mountain of it or none at all. Too much breaks people, where zero leaves them brittle. Hardship isn’t a dial where more is always better. We need to sit with that, because we will break. I did, and I am still rebuilding. We need to torch the “what doesn’t kill you” mantra, it is all lies.

We only ever hear the adversity-forged-me story from the people it didn’t crush. The ones it broke aren’t giving talks. The narrative gets written by survivors, every time. I’m a survivor of difficulty, and it hurt like hell. So I get to sound wise. I didn’t overcome adversity, though. I choose my path.

So if it wasn’t adversity, what was it?

I think it’s Tasmania. Growing up somewhere isolated does something specific to you. Everything is away. Leaving isn’t dramatic, it’s just the only way to do anything at all. So you get early, repeated experience at dropping into a room where none of your knowledge transfers. London doesn’t run on Sydney’s rules. New York doesn’t run on London’s. Bootstrapping doesn’t run on employed-person logic. Each move drops you into a game where the old map is wrong.

I’ve gone deep on my red thread, it helps to truly understand what’s driving my decisions. There’s something I keep coming back to. The hard environments, the wicked ones, where feedback is late and misleading, punish people who cling to what worked before. What I got, without knowing it, was a decade of practice at being a beginner. Starting over in an adjacent path, again and again, compounds. That part was a decision. I became comfortable losing my footing, because I’d lost it so many times it stopped feeling like falling.

I’ve realized it’s not grit. Grit is mostly just conscientiousness with a good story. This is something else. A disposition toward recalibration. A slightly suspicious comfort with being the least-oriented person in the room. But I like that, it fuels my curiosity and builds connections.

Time for honesty about the inevitable bill

Voluntary difficulty has a cost, and it compounds quietly. You have to own the consequences.

• How is it impacting my mental health?

• Who is in my inner circle? Who can I turn to? Who comes to me?

• Is my relationship with my partner healthy? Do we accept the consequences?

• Are you only building your muscle for the new?

The big question. The one I’m sitting with. When you keep choosing the hardest version of the room, what are you running toward, and what are you leaving behind you?

Voluntary difficulty is a gift right up until it becomes an escape. From the inside, at speed, those two feel exactly the same.

The one place I’ve landed with conviction: presence. Pause, reflect, be honest with yourself. If not, you’re creating a problem for your future. Acknowledging fact is a gift.

Am I the most successful Tasmanian living in New York?

I still joke that I’m the most famous Tasmanian in New York, because I haven’t met another one. I hope to find one, because I already know that connection will be special. I’ll probably end up being the second-most-successful Tasmanian in New York. But I’m very okay with that, as I know my life has expanded.

Rob D. Willis has given 3,000 tours and presentations to more than 100,000 people, and he thinks that picture is wrong from the start. The decision starts forming the first time an investor comes across you, and it gets shaped by a story in their head that you only partly control.

I see this constantly with the founders I advise. If you’re adding slides the night before a meeting, you’re protecting yourself from leaving something out, while the bigger risk is that nobody remembers what you left in. School rewarded you for proving how much you knew. The room you’re walking into rewards you for making one idea easy to repeat to the next person up the chain.

“In many cases, an executive is kind of paid not to listen to you. Their job is to filter out as much of the noise as possible to get to what’s actually important to them.”
Rob D. Willis

The research

• Investors now spend less than three minutes reviewing a pitch deck, according to DocSend’s fundraising research. Review time has fallen for three years running, to a record low. dropboxgurufocus

• The effect of a statistic on what people believe fades by 73% within a day, while a story fades by only 32%, according to Graeber, Roth and Zimmermann (2024). sufe

• Employees are interrupted every two minutes through the day, per Microsoft’s 2025 Work Trend Index. That is the attention you’re pitching into. hrexecutive

• PowerPoint edits spike 122% in the final ten minutes before a meeting, the same Microsoft report found. Most people are still fiddling with slides when they should be thinking about the room. hrexecutive

The playbook

1. Answer three questions before you build a slide. Rob borrows these from Kendall Haven: what do you want to happen, why isn’t it happening already, and who needs to make it happen. The failure mode is aiming for a cheque in meeting one, when the real goal might be a follow-up or a technical demo. Founders also forget the associate in the room has to re-tell the story to a partner.

2. Open with the problem. Rob’s order is problem, impact, solution, consequence. Leading with your answer only works when the room already agrees the problem exists. Founders usually open with the solution because they’re excited about it, and the room pushes back on something it never agreed needed fixing.

3. Cut to what the listener needs to decide. Go through your deck and ask what each slide does for the person reading it. Rob calls his early self “Mr. Data,” showing nuance and complexity nobody asked for. The failure mode is treating volume as credibility, which confuses and bores people who know less about your topic than you do.

4. Start a story bank today. Rob recommends Matthew Dicks’ Homework for Life. Open a spreadsheet, put the date in one column, and write one story-worthy moment in four or five sentences. Founders say they have no stories, when the truth is they never wrote them down.

5. Borrow the packaging, keep the point of view. Study what already works in the format you’re using. Rob started as a guide by copying the one most like him. The failure mode now is handing the idea itself to AI, which gives you the average of everything.

The worksheet

1. What do you want to happen at the end of your next investor meeting? Name one specific outcome.

2. Why isn’t that happening already? Write the most likely reason they’d say no.

3. Who else has to say yes after the person you’re meeting, and what will they need to hear?

4. Write your pitch in four sentences: the problem, its impact, your solution, the consequence.

5. Which three slides could you delete without changing the decision?

6. What story is probably already in this investor’s head about your market or founders like you?

7. Write one story-worthy moment from today in four or five sentences.

The operating rule

Decide what you want the room to do before you decide what to say.

I’ve been advising founders for a few years now, and somewhere in the last twelve months I stopped being surprised by the distinct differences between a good one and a bad one.

For context, I don’t mean good and bad in terms of career success, who they are as people, or what they build. I am talking about how they do it. There are many ways you can achieve “success,” and it is not anchored to notoriety or fortune. It is how you go about it that I really give a shit about.

“Success” has become a vacuous term for many founders, who are chasing superficial rewards and lack any real purpose. If you chase headlines, your behavior will reflect this, and it won't be pretty. Vanity is a pursuit that does not end, you will never be truly happy.

I had a VC on my podcast who told me of a founder he knew who turned down a $935M acquisition offer because he wanted to be a unicorn. Sit with that for a moment and try to rationalize that decision; if you can give me an objective reason why, I will take you out for the best NYC cocktails, on me!

How it manifests…

The bad ones start out almost defensive, they have an answer for everything, and before I even ask it. The founder talks in headlines, talks a lot, buzzwords, a lot of hype. They tell me what the company does, what the market is, what they need from me, and none of it is untrue exactly; it’s just armor. I have learned along the way that this response is a tell, a bigger pattern.

The toxic ones are a step further. They don’t just perform, they extract. I hand over strategy, models, hours of real thinking, from earned and lived experience, and get nothing back except a request for more. No curiosity about what I see. No willingness to be told something they didn’t already believe. I’ve learned that I need to end those relationships quickly, the moment I feel myself doing all the giving and see nobody listening, I now tap out.

Then there’s the third kind. The ones who tell me the real story before I ask for it. They are capable of talking openly about what scares them about the business, not the safe version of scared, the real one. They let me see the version of themselves they don’t put in a deck.

I didn’t have language for this until recently. I just knew the work that I did with the “good” ones was better every single time. Not a little better, it was categorically different. I thought it was chemistry, some people you click with, some you don’t.

I definitely don’t think that anymore. It is, in fact, a threshold, and once you see it, you can spot it in the first meeting, it jumps out early.

I went deep into the research. The tell… whether someone lets you in.

There’s a theory in psychology called self-expansion theory. It comes out of romantic relationship research, but the mechanism underneath it has nothing to do with romance.

Humans are wired to grow, and one of the fastest ways we grow is by letting another person’s perspective into our own sense of self. Psychologists call it “including others in the self.” When it happens, both people expand. When it doesn’t, nothing moves, no matter how much time you spend in the room together.

That mechanism shows up well outside romantic relationships:

• Leaders who self-disclose, who admit uncertainty instead of performing confidence, build measurably higher trust and a real readiness to work toward a shared goal, not just tolerance of one another

• Teams with high psychological safety, meaning people can say “I don’t know if this works” without penalty, are dramatically more likely to produce genuinely innovative output

• The reason isn’t that safety feels nice. It’s that half-formed, uncertain ideas only get spoken out loud when the cost of being wrong in front of someone is low

• Shared moments of awe, encountering something too big for your existing frame, produce a nearly identical psychological signature to self-expansion. It’s the same growth mechanism, just triggered fast instead of built slowly

Every closed founder I’ve worked with was protecting something, my assumption is that they had no idea, and definitely did not want to hear that. Every open one had already decided the story was more useful to me than posturing some bullshit.

That’s the whole difference between these three kinds of founders. It was never talent, or vision size, or even how nice they were. It was whether they let me in far enough to see something true, or whether I was negotiating with a version of them built to be seen.

How founders learn who they are in the first place.

Most founders don’t arrive at self-knowledge but practical self-assessment. They get there the hard way, in public, under pressure, usually while something is on fire.

There’s a well-documented pattern in psychology called post-traumatic growth. It shows up after divorce, illness, failure, any period that shatters the story you had about yourself. Roughly two-thirds of people who go through something like that report real growth afterward:

• a sharper sense of what matters

• deeper relationships

• a version of themselves they didn’t know was available

It’s not automatic. Some people come out resistant to change, or still stuck in the struggle. But growth is the more common outcome than we assume.

Founders go through a version of this constantly, just compressed. The round that didn’t close. The cofounder who left without warning. The product nobody wanted after eighteen months of certainty that they would. Every one of those is a small identity collapse. The founders who come out the other side with a clearer sense of who they are, not just what they’re building, are the ones who did something specific with the collapse. They made meaning out of it instead of just surviving it and moving on.

That’s the raw material a great collaboration runs on. It’s also exactly what a closed founder won’t show you. If they haven’t metabolized the hard part yet, or they’re still defending against it, there’s nothing underneath the pitch for you to work with. You get the polished outside and none of the true inside, and you can build a campaign on that, but you can’t build a story.

I don’t want to babysit a founder’s narrative. I want to get the real one and turn it into their superpower.

How the work grows with them

The founders who open up aren’t just easier to work with. They’re mid-process. They’ve done enough of the internal work to know the real story is more interesting than the polished one, and they’re often still finding out what it means as they say it to you.

That’s the moment self-expansion kicks in for both of you. You’re not managing their narrative anymore, you’re building it together in real time. And the result…

You both end up somewhere neither of you would have landed alone.

This is also why the collaboration itself can be the growth mechanism, not just a byproduct of good chemistry. Saying the true thing out loud to someone who isn’t going to use it against you is its own kind of progress. You didn’t just help them tell their story. You helped them find out what it actually was.

Aaron Alpeter spent years inside Unilever, The Flex Company, and Lululemon Studio before building Izba Group, and he’s since helped founders realize more than $2.5B in exits. His view is that buyers start grading you long before they make an offer. Your supplier mix, your fulfillment setup, your margins and whether the company runs when you take a week off are the real diligence, and the banker mostly reads the results out loud.

I learned this the expensive way on my first exit, where we sold 51% up front and tied the other 49% to three years of EBITDA performance. At the time I thought I’d negotiated well, and looking back, the buyer was simply hedging on me. And the pandemic bit us hard on that value.

If you’re seven months from the end of your runway and making a hundred calls a day, the exit feels like a problem for your future self. The choices you make this month are the ones a buyer will end up using to assess price, so this episode is about making them on purpose.

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The research

• CPG deal value more than doubled year-over-year in Q1 2026, even as deal volume continued to fall, with three transactions accounting for close to $120 billion in combined value (PwC, US Deals 2026 Midyear Outlook). Money is flowing, but it’s concentrating on a handful of bets.

• Megadeals now make up 47% of consumer markets deal value, up from 23% in 2024, while overall deal volumes are on track to drop 12% this year (PwC, Global M&A Trends in Consumer Markets). Capital is chasing category leaders, so being clearly best at one thing beats being decent at five.

• PepsiCo closed its Poppi acquisition at $1.95 billion, and the deal included a performance-based earnout (Food Processing). Pepsi had reportedly planned its own functional soda under the Soulboost brand before cancelling it, which likely cleared the way for the deal (CNBC via NBC). For big CPG, M&A has become the R&D budget.

• Earnouts appeared in 24% of private-target deals in 2025, and the median earnout potential rose from 31% to 34% of the closing payment (SRS Acquiom 2026 Deal Terms Study). Smaller deals get hit hardest, with 35% of deals up to $25M carrying an earnout (SRS Acquiom Lower Middle-Market Report).

• Across the deals SRS Acquiom has tracked, earnouts have paid out roughly 21 cents for every potential dollar (SRS Acquiom). If a third of your price depends on you sticking around, plan as though most of it never arrives.

The playbook

1. Write down what a buyer would actually be buying. Aaron says acquirers want three things: profitability, a unique capability, and meat left on the bone. Hero Cosmetics is the textbook case, with Church & Dwight paying $630 million, a 14X multiple of Hero’s $45 million in EBITDA, for a business the founder says was built bootstrapped (Beauty Independent). According to Aaron, a big part of the appeal was how good that team was at selling on Amazon. The failure mode is assuming your brand is the asset, when the real asset is usually a capability the buyer can spread across their whole portfolio.

2. Sequence your channels and leave room to grow. D2C is where you learn about your customer, retail is where you scale, and eventually you shift to protecting what you’ve built. Founders get this wrong by doing too much too soon in the wrong order, like expanding globally while still private. A buyer with global distribution wants that growth still ahead of them because it’s how the deal pencils out, so every market you enter early is upside you’ve taken off the table.

3. Build it to run without you. Earnouts exist because buyers fear key person risk. Aaron sees growth-stage companies bring in a CEO and fill out the exec team roughly 18 months before targeting an exit, so the buyer inherits people with a five-year plan instead of founders about to cash an eight-figure check. The failure mode is identity, because once your self-worth is tied to being the final decision maker, you become both the bottleneck and the discount.

4. Run ops like someone will audit them. Supplier diversification, clean fulfillment contracts, and documented processes are what survive diligence. Aaron also flags a newer trap, where one or two person brands running on agents post huge margins that strategics can’t confidently price, so some are hiring people back before a sale. The failure mode is optimising for a margin that only exists because nobody’s there to run the business.

5. Decide what exit you actually want. A full sale, a majority investment where you work a few hours a week, or a business you run for decades all demand different builds, and Aaron’s point is that being honest about this early changes every decision after it. The failure mode is raising money you didn’t need, then watching a $15M offer that would have changed a bootstrapped founder’s life turn into a bad outcome after dilution.

Build it so someone else could run it tomorrow, then decide whether you want them to.

The best venture returns in America this year came out of Washington, DC.

PitchBook has DC delivering an 11.7x MOIC through August 3, 2026, against 3.74x for the Bay Area and 3.18x for New York. The city best known for politics beat Silicon Valley roughly three to one.

What grabbed me was the next data set I found. When Revolution’s Rise of the Rest ranked where each state’s investors put their deals, DC-based investors backed companies in California, New York, Texas, Florida and Virginia most often, and DC itself didn’t make its own top five. pitchbookchristopherwink

If you’re a first-time founder outside the Bay, you’ve probably lived a version of this. You build a pitch list from the famous firms, book the flights, and spend weeks explaining your market to people who’ve never set foot in it. Meanwhile, the operator who spent 20 years in your industry lives four suburbs away and has never been shown a deal. Knock on their door (if you know them!)

Local capital rarely funds your Series A. What it does well is get you to the point where a Series A partner takes you seriously, and it comes from people who understand your problem without a translation layer. This week is about raising where you’re understood first.

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The research

• DC’s standout year sits well above the national line. Across all metro areas, the median MOIC is now 4.1x, up from 3.6x in 2025 and 2.6x in 2024, with smaller hubs like Miami and Phoenix also outperforming the coasts. (PitchBook, August 2026) pitchbook

• The money is still flowing the other way. Bay Area and New York funds captured roughly 65% of new commitments in 2025, and PitchBook’s longer-run returns-by-series model still favours the coasts. One strong year is a snapshot, which is why the regional edge matters most at the earliest stage. (PitchBook Q1 2026 Analyst Note) pitchbook

• Proximity still drives who writes the first check. In the average state, 37.6% of startup deals include an investor based in the same state. (Rise of the Rest 2026, PitchBook data) christopherwink

• The DMV is split down the middle. DC’s local participation rate sits at 12.5%, while Maryland is at 40.2% and Virginia at 47.9%. The founders are local. A lot of the capital isn’t acting like it. (Rise of the Rest 2026) christopherwink

• Your first local check may come from public money. In 30 of 50 states, the most active in-state investor in 2025 was a state-backed or public-private fund. (Rise of the Rest 2026) christopherwink

Stop flying past the people who already understand your market.

The playbook

1. Map your backyard before you book a flight. Build a list of every angel group, state-backed fund, university fund and operator-turned-investor within an hour’s drive. In the DMV, TEDCO was Maryland’s most active in-state investor and the Virginia Innovation Partnership Corporation led Virginia, so start there. The failure mode is opening with the famous-firm list because it feels like the real game, then learning three months later that those partners pass on markets they can’t see. christopherwink

2. Make your geography part of the pitch. If you’re building near agencies, contractors, research universities or health systems, that access is a moat, so say it out loud. Local investors can underwrite that knowledge in one meeting, while out-of-town investors tend to discount it. The failure mode is sanding off your location to sound like a San Francisco company, which throws away the one advantage nobody on the coast can copy.

3. Get on a stage where the room is already warm. Regional pitch competitions and demo days put a room of local angels and VCs in front of you at once, which beats 40 cold emails. The failure mode is treating the event like a trophy hunt. The win is the list of people who leaned in, so send each of them a one-page update within 48 hours while you’re still top of mind.

4. Let local conviction earn the national round. Local checks are often small, so stack them into proof: a pilot with a regional customer, a lead investor who knows the market, a round that closes fast. Take that proof to the coastal funds once you’ve earned it. The failure mode is treating local and coastal as either/or, or collecting 30 tiny checks with no structure. Ask your lawyer how to pool them before you say yes to the first one.

The worksheet

Set a 20-minute timer and answer these for your own company.

1. Name five investors within an hour’s drive who have backed a company in your sector or a neighbouring one.

2. Which local institution (agency, university, health system, big employer) gives you access that an out-of-town competitor can’t easily get?

3. Write the one sentence in your pitch that explains why building in your city is an advantage.

4. Which operator in your market has lived your customer’s problem, and have you asked them for advice or a check?

5. What’s one regional pitch event, demo day or angel group meeting in the next 60 days you could get in front of?

6. What proof (pilot, customer, local lead) would make a coastal fund take your next meeting seriously?

7. If three local angels said yes tomorrow, how would you structure their checks?

Where to go this month

If you’re building in DC, Maryland, or Virginia, Battle of the Regions is the stage I’d point you at. It’s a startup tournament built by District Angels, a volunteer-led investing community. The Maryland regional is October 7, and the Championship is October 23, live at DC Startup & Tech Week. Every winner gets listed on Play Money, where angels anywhere can read the deal, ask questions, and invest. Full disclosure: I’m Head of Growth at Play Money, so weigh the recommendation with that in mind.

*Investing through Play Money requires accredited status, with details at letsplaymoney.com/dmv.

A customer hears the hype, carves off some budget to experiment, and signs. It lands in their ARR line looking exactly like traction. Six months later somebody runs a budget review, and the curious customers quietly leave.

Vanessa has sat on every side of this. Product leader, founder who sold her company, NEA partner, and now co-founder of her own firm. Her point is that founders and investors look at identical data and regularly reach opposite conclusions.

If you’re sitting on your first real bookings and wondering why investors seem less excited than you are, the gap usually comes down to which signals you’re counting. That’s fixable.

Vanessa Larco is cofounder of Premise VC, backing early-stage software founders.

The research

• ChartMogul’s 2025 retention data showed AI-native companies with a median gross retention of just 40%, worse than B2C products. That gap is curiosity walking out the door. Growthunhinged

• MIT NANDA’s July 2025 report found 95% of organizations in its research saw no measurable return from their generative AI initiatives. Your customer’s experiment is on someone’s review list. letsdatascience

• CRV reports that usage depth, meaning whether customers have AI embedded in daily workflows or are still experimenting, is now its own diligence layer, and that presenting pilot activity as commercial traction is a recurring pitch mistake. CRV

• Carta’s Peter Walker puts the share of seed companies raising a Series A within two years at around 20% in 2025, with bottom-quartile seed companies graduating at roughly half that rate. Pmf

• SVB data cited on The PMF Show puts the median ARR to raise a Series A at about $3.5M, up from roughly $1M a few years ago. Only revenue that renews gets you there. Pmf

Just because you have a bunch of bookings doesn’t necessarily mean Product Market Fit. Now there’s product curiosity fit. Vanessa Larco

Key lessons from Vanessa

1. Your old skills are your edge. Vanessa walked into NEA believing she was throwing away a decade of product experience. It became the foundation of how she invests. Deciding what to build next and deciding what to back run on the same muscle: weighing signals, picking what matters, ignoring the rest. Whatever you did before founding is doing more work for you than you think.

2. Numbers can lie as well as anecdotes. Vanessa makes a contrarian case that qualitative data can be more objective than quantitative. You can slice a dataset to support almost any argument, and it feels black and white, so nobody questions it. The data shows you what’s happening. People fill in the why with whatever they already believed.

3. Fit is in the eye of the investor. When a founder values the same signals Vanessa does, she has conviction. When she doesn’t, she passes, and someone else might lean in. That shared view of what counts is worth more than the cheque, because it makes every hard decision after the raise easier.

4. Every round is a different game. Pre-seed and seed back the founder and how they make decisions. Series A backs execution and whether you can grow into a public-facing CEO. Series B is proof in the numbers. Later rounds are about the exit multiple. What won the last round won’t win the next one.

5. Hiring swaps your problems. One founder told Vanessa it would all get easier once the team doubled. She told him he’d be trading product problems for people problems. Grow slowly if the product is what you love working on.

6. Keep one thing you love. Jeff Lawson built with unreleased Twilio APIs on weekends and showed up Monday with notes. Aaron Levie still obsesses over customers and two-pixel drop shadows at midnight. The CEOs who last hold onto the part of the job that made them start.

7. Constraints breed creativity, and repair beats avoidance. Bluey builds a whole game out of a balloon. SoftBank handed companies $100 million before they needed it and drowned them. Vanessa and her co-founder want tension in their decisions. The skill is repairing conflict, because if you never disagree, you’re not pushing hard enough.

The worksheet

1. For your three biggest curious customers, what specifically would need to happen for them to renew?

2. Write the three signals you’d point to if an investor asked “why do you believe you have product market fit?”

3. Which of those signals is quantitative, and what’s the qualitative story behind it? If you can’t explain the why, who will you call this week to find out?

4. Which round are you raising next, and what does an investor at that stage care about most? Is your current deck built for that, or for the last round?

5. What’s one constraint you’re trying to raise or hire your way out of that might be forcing better decisions?

I am a vulnerable person. I see it as a superpower, but it has taken me years of active reflection to understand the code of my character.

Hidden Potential is really a book about how people “become”. Not whether they have talent or genius. More like what conditions help ordinary people compound into exceptional ones over time.

The interesting spin is that Grant leans heavily on research showing growth is less about raw intelligence and more about character skills and learned habits. These are what shape how someone responds to friction, feedback, uncertainty, and repetition.

Founders obsess over many things in their startup, while their internal operating system quietly runs the whole company from a dark place in their minds that they do not even know exists.

The distinction that matters here is simple.

• Personality is how you’re wired, like “I’m introverted.”

• Character is what you do when things get hard, and the research says you can train it. Character behaves more like a muscle than a tattoo.

Test yourself out

When you’re seven months from zero, every problem looks strategic, whether it’s pricing, hiring or the raise. More often the bottleneck is one behavior you keep repeating under stress, and no strategy survives a founder who keeps dodging the conversation that would fix it.

The filter question to sit with this week: what situation keeps knocking you off balance, and what do you do instead of facing it?

What the research says

Grant leans on a few bodies of work that line up pretty neatly for founders.

The first is scaffolding, a term coined by Wood, Bruner, and Ross in the 1970s. People improve fastest when a challenge sits slightly above their current ability, feels emotionally survivable, and comes with feedback. Too easy and you stagnate, too hard and you shut down. Founders tend to overshoot straight into chaos and call it ambition.

The second is deliberate discomfort. Anders Ericsson’s work on deliberate practice and Carol Dweck’s growth mindset research both point the same way: improvement speeds up when you keep walking into situations that make you feel mildly incompetent. Most adults build an entire identity around avoiding exactly that feeling. For a founder, it means dropping the performance of expertise long enough to learn something.

The third is confidence. Albert Bandura’s self-efficacy research found that mastery experiences, the small wins you actually earned, are the strongest source of belief in your own ability. You will not feel ready first. Readiness is usually built after the fact, out of evidence you collected while you were still unsure.

The last thread is culture. People adapt to whatever gets rewarded, so a startup that only celebrates the closed deal teaches the team to hide weakness and protect ego. Reward curiosity, coachability and experiments that failed usefully, and you get a team that learns faster than the market moves.

The framework: the Character Reps Sprint

Four weeks, one skill. Think of it as a psychological gym you visit three times a week.

Week 1: find the hidden ceiling. Ask yourself what repeatedly drains you, what you avoid, where you overcompensate, what feedback keeps coming back, and who you become under stress. Then pick the one character skill that would most change your trajectory if it got stronger. Be specific. “I avoid difficult conversations” is useful, while “I want to be a better leader” gives you nothing to train.

Week 2: build tiny exposure reps. Each rep should feel uncomfortable, measurable, and survivable. If the skill is courage, send one uncomfortable outreach a day and make one direct ask without overexplaining. If it’s listening, speak last in meetings and ask three follow-up questions before giving advice. If it’s resilience, write down a setback within ten minutes, pull one lesson from it, and retry within 24 hours.

Week 3: close the loop. At the end of each day, jot down the rep you did, the emotion that showed up, the story your brain told you, what actually happened, and what you learned. If you have an advisor/mentor, check in weekly on consistency, never on outcomes. You’re rewarding the behavior because the results lag.

Week 4: update the identity. Ask what got easier, what resistance weakened, and what surprised you. Then rewrite the sentence you tell yourself. “I’m bad at sales” becomes “I’m someone who practices courageous communication.” It’s a tiny wording change that shifts the whole weather pattern in your head.

One skill, measured by reps, is the entire design.

Tiny reps beat giant motivational speeches every time.

None of this is overnight transformation. It works more like building your 401k, wearing running shoes, a small uncomfortable deposit every day that looks like nothing until it looks like a different founder.

Then she became a founder herself. Her first startup, Nosy, landed two investment offers on Dragons’ Den UK and generated more than one billion views with less than $5,000 in media spend. Today, Favikon ranks her among the Top 3 LinkedIn Voices for Sales and the Top 10 for Venture Capital.

Here’s the tension. Founders treat a raise as the win. Carina treats capital as fuel, not proof. For her, the proof is traction, and fundraising is just another sale. Capital should scale something that is already working, not fund the process of figuring out whether the theory works in the first place.

Before you can change that, she says you have to see the system you inherited. Raise big. Grow fast. Exit. Nobody chose those rules. Most founders just accept them and call it strategy.

Fact sheet

• Only 63 percent of first-time VC managers who raised a debut fund go on to raise a second one, per PitchBook, despite often outperforming established firms on returns.

• As many as 75 percent of venture-backed companies never return cash to their investors. Harvard Business School research covering more than 2,000 startups.

• Fewer than half, 48 percent, of seed-funded startups manage to raise a follow-on round at all, according to a CB Insights analysis of over 1,100 companies.

• Roughly 85 percent of startups that raise a Series A never make it to a Series B.

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Carina Cunha: Building an investment bank and writing a book on human consciousness. She structures capital raises across venture, debt, and private equity, work that showed her a broken system up close. She’s advised over 100 companies from pre-seed to IPO.

The constraint

Founders inherit a system that was built by many before them. Raise big, grow fast, exit. Nobody sits you down and asks if that’s actually the outcome you want. Here’s the question to hold against your own situation. If nobody ever told you that raising was the goal, would you still be chasing this round, or would you be building the business you actually have?

The framework

Carina’s framework is capital as energy, not capital as validation. Money is fuel. It buys you time and speed, nothing more. The failure mode is treating a check as proof you’re right. It isn’t. It’s a loan against your future decisions, and every investor who writes it wants something back, whether that’s board control, a specific growth curve, or an exit on their timeline instead of yours.

Here’s the edge case that trips people up. You can take capital and still lose the operating system fight, because the money changes who you answer to before it changes what you can build. Carina’s filter for founders raising with no traction and no leverage: stop pitching a story about the market size and start being honest about what you’re actually good at and what problem you’ve actually solved, even if it’s small. Investors can smell a TAM slide that’s doing the talking instead of the founder.

The pattern underneath all five: the person across the table asking about your traction may not have any of their own. Discernment goes both ways.

Worksheet:

Before your next investor conversation, answer these honestly.

• What decision have I made this month that was actually about the business, versus about what a raise would let me say?

• Where is my energy leaking right now, and would more capital fix that or just fund it faster?

• If this investor’s fund never raises a second one, what do they actually want from me?

• What can I say about my business today, with no spin, that would still make someone want to back me? The facts!

• What am I optimizing for? The round, or the company?

The operating rule

A raise is not the goal. It’s a tool, and tools only work when you know exactly what you’re building with them.

Why I Started a Playlist for Founders

I’ve been sitting with this idea for a while and I finally just have to write it down.

Music has never been background noise for me. It’s been the thing running underneath every version of my life, long before I ever called myself a founder.

I started my career in creative technology, working at the intersection of brands and artists. I co-founded Listen, a sonic branding agency, and spent years figuring out how sound and music actually move people, not just entertain them. Across my career I have worked with Microsoft, Visa, Smirnoff, Red Bull, Tinder, and Ford. Every one of those projects came back to the same question. Why does music get under people’s skin faster and deeper than almost anything else a brand can do?

Turns out there’s a real answer, and it’s not marketing theory. It’s biology.

The ears got there first

Long before humans could talk, we could hear. Bony fishes were the first organisms with hearing, something like 400 million years ago. Eardrums showed up around 250 million years ago. Human speech didn’t arrive until roughly 200,000 BC. Ears had a 400 million year head start on words.

That order matters more than people realize. Sound reaches your brain 20 to 100 times faster than sight does. It hits before you’ve had a chance to think, which means it shapes every perception and thought that follows. Your brain is also, in a strange way, a sloppy drum machine. It’s constantly hunting for rhythm and pattern, in a familiar voice, in birdsong, in rain on a window. Sound gets in, and it stays there.

I wrote about this back in 2017 for Fast Company, when I was running Listen. The piece was about why brands needed to rethink their relationship with music, moving past a single song in a commercial toward something built on defining what they sound like. Music is a cultural universal. It’s one of the only things every society on earth practices and celebrates, in some form, without exception. Almost a decade later, I still believe that line more than almost anything else I’ve written.

The numbers back up the feeling

I’ve spent years around research on this, and the data never stops surprising me. I ran a large study of Australian music fans, 86% agreed that music is integral to who they are. That number barely moves across generations. Gen Z sits at 87%. Baby Boomers sit at 86%. Whatever gap people assume exists between a 22 year old and a 60 year old when it comes to music, it isn’t there.

People also spend real time with it. Average daily music streaming came in at 3.1 hours. And when people love an artist or a song, they don’t sit on it. 67% said they actively seek out and share new music with people around them, and that instinct doesn’t fade with age either.

Here’s the part that always gets me. When researchers asked people who inspires them, musicians ranked second only to friends, ahead of entrepreneurs, athletes, and celebrities by a wide margin. Music doesn’t just move people emotionally. It shapes who they look up to and how they see the world.

Where this lands for me now

I’m not running a sonic branding agency anymore. I’m building Startups Decoded, talking to founders every week about the messy, unglamorous work of building something from nothing. But the thread never actually broke. Every founder I talk to is trying to do the same thing music does without even knowing it. Cut through noise, create a feeling, build something people carry with them.

I’ve also noticed something about my own process. On the hardest days, when a founder’s story isn’t landing, or a script isn’t coming together, music is what gets me back in the room. Not lyrics I’m trying to analyze. Just the right track at the right moment, doing exactly what it’s always done for humans, giving my brain something to hold onto when everything else feels loose.

So I’m starting something small. Every week I’ll drop a playlist called “Music for Founders”. No theme, no forced narrative, just what’s actually on repeat while I build. Some weeks it’ll be moody. Some weeks it’ll be something to lift you up.

If you’re building something right now, drowning in decisions, running on less sleep than you’d admit to anyone, I get it. I’ve been there three times over. Music isn’t a fix for any of that. But it’s one of the oldest tools humans have for getting through hard, uncertain stretches, and it’s been doing that job for a couple hundred thousand years before any of us showed up.

New tracks drop every week.

»» Available now ««

Nobody sits a first-time founder down and tells them that incorporating alone creates a legal board, whether they’ve thought about it or not. Nobody tells them that a small check from an angel can come with a request for a board seat they didn’t need to give away. Nobody tells them that the safe they’re so relieved to close comes with almost no strings, right up until the priced round, when every string shows up at once.

I learned this the hard way, twice. Both my exits taught me the same lesson: the people advising you in year one usually haven’t made these calls before either. So I brought together a J.P. Morgan Asset Management advisor, an early-stage investor from Girl Math Capital, and a governance lawyer from The Fourth Effect in one room, in front of 60+ founders, and asked them to lay out exactly what happens before anyone tells you it’s happening. Board composition, deal terms, and what to do with the cash once it lands.

The single biggest takeaway: the decisions that feel small and procedural in month one are the ones that decide how much control you actually have by Series A.

Presented by J.P. Morgan

Helping venture-backed founders navigate the financial decisions that come after the term sheet. From capital preservation to liquidity strategy, we help companies make the most of every dollar they raise.

The constraint and filter question

• The friction point is this: founders don’t know which early decisions are permanent until they’ve already made them.

• Ask yourself right now: who is legally on your board, and can you name one decision they’ve formally ratified in the last quarter? If you can’t answer that cleanly, you’re exposed.

The framework

Here’s how the board actually evolves, whether you plan it or not. At incorporation, you and your co-founder are the board by default. No fundraise needed, no paperwork beyond the entity itself. At seed, if an investor writes a big enough check, usually somewhere between 10 and 20 percent of the fully diluted company, they can negotiate a board seat that comes with real fiduciary weight, not just a friendly check-in. At Series A, a third kind of seat shows up: the independent director, someone without a stake in either the founder’s or the investor’s agenda.

The mistake almost every first-time founder makes is doing nothing about the board until the investor director is already negotiated into the term sheet. By then, you’ve lost the leverage to choose who sits in the independent seat, and the room can tilt against you fast if there’s only one founder director across the table from one investor director. The fix is proactive, not reactive. Seed or seed-plus is the moment to start seating your own independent, before you’re forced to accept whoever the lead VC recommends. If you’re not ready for that, promote a trusted advisor to observer status first. They sit in the room, they don’t vote, and you keep control of who eventually earns the real seat.

The same logic runs through fundraising structure and cash management. A SAFE gives you almost total freedom because the investor has almost no formal claim on your decisions. A priced round changes that instantly, because now there’s a class of preferred stock with real shareholder rights attached, whether or not the investor takes a board seat. And once the money is actually in your account, the framework simplifies to three priorities in order: preserve the principal, keep it liquid enough to access when you need it, and only then think about yield. Founders who skip straight to yield, chasing an extra half point of return on money they’ll need in ninety days, are optimizing the wrong variable.

“Something that takes you five minutes now can save you eight hours in the future, if not more.”

The data

• Founders retain voting control in 71% of companies post-Series A, down from 88% at seed, according to First Round Capital’s analysis of over 300 portfolio companies (PitchBook, Q4 2024, n=1,204 Series A rounds).

• The typical board structure moves from three seats at seed (two founders, one investor) to five at Series A (two founders, two investors, one independent), and can flip to investor-majority by Series B.

• 34% of co-founder disputes that ended in a founder exit were preceded by an equal equity split at incorporation, compared to 19% for unequal splits, per First Round Capital’s 2024 founder survey.

• Lead investors typically negotiate a board seat only when their check represents 10 to 20% of the fully diluted company. Smaller checks are increasingly offered observer rights instead, a compromise that preserves founder control without shutting out valuable investors.

• Qualified Small Business Stock (QSBS) can shield founders from significant capital gains tax at exit, but moving too much post-raise cash into non-qualifying investment vehicles can jeopardize that exemption entirely, a detail that rarely comes up until it’s too late to fix.

The playbook

Run this sequence before you’re forced into any of it by a term sheet:

1. Incorporation. Confirm who is legally a director today. Write down every material decision you’re already making.

2. Pre-seed to seed. Choose one or two trusted advisors and formalize observer rights before you need to fill a real seat.

3. Seed to seed-plus. If you’re not seating an independent yet, get directors and officers insurance in place. If a carrier will underwrite you, you’re ready.

4. Before any priced round. Get a clean cap table, historical and projected financials, and a use-of-funds narrative that answers two questions: why are you burning what you’re burning, and what milestone does this raise actually buy you?

5. After the round closes. Split cash into three buckets by timeline: three to six months of burn in checking and savings, the next stretch in a money market fund, and nothing chasing yield that you’ll need before it matures.

The worksheet

Before your next fundraising conversation, answer these on paper:

• Who is currently on my board, and have we documented a single decision this quarter?

• If my lead investor asked for a board seat tomorrow, do I know what percentage triggers that request, and am I prepared to negotiate it?

• Do I have one advisor I trust enough to give observer rights to before I need an independent director?

• Can I state, in one sentence, why I’m burning what I’m burning and what this raise gets me?

• If the round closed today, do I know exactly which bucket, checking, savings, or money market, each dollar goes into?

The operating rule

The decisions that feel too small to matter in month one are the ones deciding how much control you have by Series A.

Disclaimer

The views and opinions shared on Startups Decoded are for informational purposes only and do not constitute investment or legal advice. Always consult a qualified professional before making any financial or legal decisions.

Open your feed. Open your inbox. Open LinkedIn, if you can stomach it.

It all feels weird, like everyone’s talking, and somehow it’s louder and emptier at the same time.

You’re not imagining it. That’s just what the internet is right now.

The Situation

AI didn’t just enter the content game. It flooded the field.

An OECD tracker that monitors AI-related content incidents in the media went from about 50 a month in early 2020 to nearly 500 a month by January 2026. Ten times more, and the growth has doubled in just the last year. Ahrefs went and checked actual web pages, and found close to three-quarters of them now carry some AI-generated content. Axios reported that AI-written articles briefly overtook human-written ones online back in late 2024. They’ve been running neck-and-neck ever since.

So…more content than ever, made faster than ever, by fewer humans than ever.

Here’s the part most people miss. People noticed, and they don’t love it!!

• Animoto’s 2026 State of Video Report found 83% of consumers say they’ve watched a video they suspected was AI-made, and more than a third said spotting it made them trust the brand less.

• A December 2025 survey from Klaviyo, covering 8,000 people across eight countries, found something sharper: when consumers clock AI in a brand’s marketing, they’re four times more likely to trust that brand less. A real cost.

• A 2026 Raptive study found half of US consumers now check multiple sources before they believe what they read online.

Put those things together, and you get the actual situation: an ocean of content, and an audience that’s getting better at telling which parts of it came from a person.

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The Opportunity

Here’s the flip side, and it’s the good part.

When everyone can generate infinite content, infinite content stops being worth anything. What’s left is the stuff that’s actually, unmistakably someone. A real point of view. A story only you could tell, because you’re the only one who lived it.

That’s not a content play. That’s a trust play. And trust is the thing that was never going to scale, no matter how good the tools got.

For founders and investors, this shows up in the places that actually move a business: who gets on your cap table, who takes your call, who you get to hire, who introduces you to who. People don’t back the loudest founder. They back the one whose thinking they’ve been quietly following for a while, the one who feels like a known quantity before the first meeting even starts.

The window on this is wide open right now, but it won’t stay that way. Every founder who gets specific and human while everyone else is pumping out generic AI slop is banking trust the others can’t buy back later. The ones who wait will be trying to stand out in a room that’s gotten a lot louder.

How To Approach It

Most founders hear “tell your story” and picture a content calendar. That’s the wrong instinct, and it’s why most of it doesn’t work.

The story is already there. You’ve said it a hundred times, on calls, in pitches, at the bar after a bad week. Problem is, it’s scattered, and it never makes it out of the room in a form anyone remembers.

Three things, in order:

1. Find what’s already true. Not a brand exercise. Go back through what you’ve actually said, the posts, the pitches, the interviews, and find the lines you keep repeating without noticing. That repetition is the tell. That’s your real story, hiding in plain sight.

2. Get it out of your head and onto the record. This is the part almost everyone skips, and it’s the part that actually matters. A real conversation, on video, about what shaped you, what you believe, what you’ve earned the right to say. Not a content brief. A human one.

3. Build something that keeps running. A story you tell once is a nice LinkedIn post. A story that’s built into a system, feeding your pitch, your hiring, your press, your investor updates, off the same throughline, is a compounding asset. That’s the difference between people knowing you exist and people trusting you before they’ve met you.

Do that, and you’re not adding to the noise. You’re the reason someone stops scrolling.

Brett Turner learned it the other way around. Twelve years as a CPA, then a controller, then a CFO across a string of startups, some of which failed spectacularly, before he ever founded one of his own. By the time he built Trovata, his seventh company, he had already seen every version of what a cash crisis looks like from the inside.

That order matters more than people admit. Most first-time founders build the product first and back into the numbers later, treating finance as a chore they will hire their way out of eventually. Brett’s story argues the opposite. He treats cash flow, liquidity, and your own control board as the operating system running underneath the business, not a support function you delegate the moment you can afford it.

The data

• Running out of cash is now cited as the proximate cause in up to 70% of startup post-mortems, though the root causes usually start earlier, with product-market fit and team problems doing the real damage. Review42

• About 29% of startups point to running out of cash as the actual root cause, not just the trigger that finished the job. Review42

• Roughly 80% of startups operate without a CFO in their early stages, meaning the numbers usually sit with a founder who never trained for the role. Embroker

• A 2026 Ripple survey of over 1,000 finance leaders found 74% believe stablecoins can boost cash flow efficiency and unlock working capital currently trapped in slow settlement. StablecoinInsider

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The workbook

1. Pull your last three months of bank data and compare it against your P&L. Where do they disagree, and can you explain why in one sentence.

2. Name the three or four numbers that actually run your business, revenue, COGS, OpEx, EBIT, whatever they are for you. Could you recite them from memory right now?

3. Check whether you have filed an 83(b) election if you hold founder stock. It is two pages, and it can save you real money later.

4. Look at your cap table like a stranger would. Does it read clean, or does it look like a decade of decisions nobody explained?

5. Decide honestly whether you need a full CFO, a fractional one, or just better tooling right now. Timing this wrong is expensive either way.

Big ticket items to action

1. Set a monthly cash review separate from your P&L review. Cash and profit tell different stories, and only one of them can bankrupt you fast.

2. Get your bank data and your books talking to each other automatically. Manual reconciliation is where good decisions go to die.

3. Build one simple cash forecast this quarter, even a rough one. A bad model beats no model every time you need to make a call fast.

• The situation: why most advisor deals lack process

• What 2026 data says about paying advisors. Cash Vs Equity

• How to find, vet, contract, and work with an advisor

• Announcing “Stump the Advisor”, a livestream for founders to ask me their big questions and get free advice

• Want $500? Send me a founder, they join my Advisory, $500!

The situation

Most founders build their advisor bench by accident. A friend introduces someone, a LinkedIn DM turns into a coffee. Six weeks later, that person has 0.5% of the cap table, and nobody remembers agreeing on what they’d actually do for it.

That’s not an advisor relationship… It’s gifting equity. This model, of course, does not scale. They don’t get you unstuck when cash is tight, and they definitely don’t add value on the right thing at the right time. Likely more interested in their vesting.

The advisor market has grown up around founders faster than founders have grown up around it. There are more people calling themselves advisors than ever, more frameworks for compensating them, and still almost no consistency in how founders actually run the process. This issue is about fixing that.

One number worth sitting with

Many founders say their advisors genuinely add value to the business. But there are so many who don’t.

That gap isn’t about talent. It’s about structure. Founders typically skip the right steps: so there is no clear role, no defined time commitment, no way to exit the relationship if it stops working. It can become almost toxic

What 2026 research says

• Advisor equity typically lands between 0.1% and 1% of fully diluted shares, with most advisors receiving 0.25% to 0.5% vesting over two years, allocated monthly.

• Time commitment sets the range: a casual advisor giving one or two hours a month sits at 0.05% to 0.15%, while someone in the room ten+ hours a month can reasonably ask for 0.25% up to 1%.

• Equity shrinks as the company matures. Pre-seed advisors are landing around a 0.21% median as of last year, down slightly from 0.25%, and only about one in ten pull 1% or more.

• Cash is back on the table for transactional or short-term help. Active advisory roles are commanding cash retainers in the $500 to $2,000 a month range, on top of or instead of equity.

• The FAST agreement is the closest thing this space has to a standard. It’s a template originally built by the Founder Institute, and the standard structure is two years with monthly vesting starting from the date the agreement is signed.

None of these numbers matter if the relationship isn’t structured right in the first place. Which brings us to process.

Finding, interviewing, contracting, collaborating

1. Finding. The best advisors rarely apply for the job. As one founder put it in the research, a true advisor doesn’t ask you to make them one, they show up adding value, and the title just catches up. Look for people already in your orbit giving good advice for free. That’s your shortlist.

2. Interviewing. Treat it like a hire, not a favor. Ask what specific problem they’d help you solve in the next 90 days. If the answer is vague, that’s your answer. On my podcast, Breen Sullivan from The Fourth Effect (An Advisory Platform) made a point that’s stuck with me: advisory relationships should be fit for purpose, built around what you actually need right now, not a static board you assemble once and never touch again.

3. Contracting. Write a role summary before you write a cap table line. What do they do, how often, for how long. Set a vesting schedule with a cliff, and build in a pause or exit clause both sides can use without it turning nasty. I’ve watched a founder remove three advisors in one sitting because they’d committed to a role and simply never showed up. She was right to do it, and every good advisor should want that accountability.

4. Collaborating. Revisit the relationship every quarter, not just when something’s on fire. If they’re not moving the needle, that’s not a betrayal, that’s the system working. If someone’s not driving value, you should be able to exit them. That’s fine.

Announcing!!! Stump the Advisor

I’m launching a live series called “Stump the Advisor” with a rotating lineup of partners. I will be on the hot seat, a cohost runs the queue, pulls a founder’s hardest, messiest problem live, and hands me the mic cold. I solve it in real time, in front of everyone. It’s a genuine test of pattern matching under pressure, not an AI cheat.

We have two amazing co-hosts booked already. I will promote it across every channel I’ve got, and package the recordings for all of our communities afterward. If you’ve got a problem you think might actually stump me, keep it. That’s the point.

I will announce dates, partners, and RSVP details soon!!

$500 for the right referral*

I run a Founder advisory practice alongside the podcast, direct access, no forms, no AI, just me. If you know a founder who needs that kind of unfiltered help and they sign on for a month, I’ll pay you $500. Simple as that. *There are terms, always terms :)

Email hello@startupsdecoded.com and introduce me today.

What they haven’t done is the math. How many conversations does one check actually take? How long does the whole thing really run? What does a messy early cap table cost you two years from now, quietly, when nobody’s looking?

Vadim Gordin (Healing Healthtech) has spent years closing that gap. He ran a venture studio inside NYU Tandon that helped 300 teams raise $2.7 billion, then built a custom dataset of first-person fundraising accounts to answer the question nobody else was tracking: not who got funded, but what it actually took to get there.

What the research says:

• Warm intros convert at 8 to 12% from intro to meeting. Cold emails convert at 2 to 4%. DocSend, via The VC Wire

• The median time to close a seed round hit 142 days in 2025, more than double the 68 days it took in 2021. Carta, via HummingDeck

• About 18.5% of US households meet the SEC’s accredited investor test. Only a small fraction of those ever write an angel check. Walnut

• Roughly one in four companies that pitch angels actually get funded. Walnut, citing UNH Center for Venture Research

• Angels provide close to 80% of outside equity for early stage startups, more capital sources than most first time founders ever think to tap. Center for Venture Research / NVCA

None of that is random. It’s the mechanism behind everything Vadim describes.

The story that anchors this episode isn’t a single company, it’s a pattern Vadim kept seeing across hundreds of raises. Founders would land twenty real conversations and walk away with one or two checks, every time, regardless of industry. They’d treat that ratio like a personal failure. It’s not. It’s just the shape of the funnel. Vadim built his entire coaching practice, an 80% follow-on funding rate at his last NYU cohort, around teaching founders to trust that math instead of panicking inside it.

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The constraint.

Founders treat the friends and family round like a warm up. A box to check before the real fundraise starts. Vadim’s data says that’s backwards. The habits you build raising your first dollars, how you track conversations, how you manage expectations with people who love you, are the same habits that will make or break your Series A cap table two years later.

The framework.

Vadim calls it the traction funnel. The idea is simple: every relationship with a future investor moves through a stack of increasing commitments. A stranger agrees to a conversation. Then they share information. Then they run a small pilot. Then they sign something real. Each step earns you the right to ask for the next one.

• The trap most founders fall into is skipping straight to the ask. They want a check before they’ve earned a conversation, let alone a pilot.

• The other trap is pacing. Vadim contrasts the marathon fundraise, an exhausting, open ended drip of asks, with the sprint, where founders lock in a follow up meeting before they leave the first one, build urgency with real traction updates, and close a tight window on purpose.

“Nobody who could have raised an angel round should fail to do so if we give them adequate information.” Vadim Gordin

The workbook

Pull up your own numbers and answer these before your next investor conversation.

1. Count your last twenty investor conversations. How many turned into a second meeting, and how many of those turned into a check.

2. Are you running a sprint or a marathon right now, and did you actually choose that, or did it just happen to you.

3. List your last five investor intros. How many came from someone who has actually written a check into that person’s portfolio.

4. Write down your guardrail number, the dollar amount and time horizon you and your household have agreed on before this raise puts real strain on your life.

5. Pick one gap in your process, meeting conversion, check conversion, or intro quality, and name the smallest fix you could test in the next two weeks.

Healing Healthtech

Healing Healthtech is a field guide and podcast for builders working to create effective digital health interventions. Only new mistakes.

By Vadim Gordin

Everyone’s going to talk about the number. I want to talk about what he actually built to get there.

The big idea

Shetty didn’t win that deal because of reach. Four media companies bid on him when his old contract expired, and none of them were bidding on download counts alone. They were bidding on the fact that people believe him. That belief is what lets a brand borrow his audience and know it’ll convert.

Here’s the part that matters for founders. You don’t need $100 million or a Netflix call to build the same asset. You need the same mechanism, just at your scale. Trust compounds the same way whether you’ve got eight employees or eight hundred thousand downloads. The math doesn’t care how big you are, it cares whether people believe you.

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The constraint

Here’s the wall you’re actually up against. Advertising doesn’t work the way it used to, and it’s not close.

People have spent the last two decades learning to filter out anything that smells like a pitch. Edelman’s newest research shows the world pulling inward, people trusting smaller, familiar circles more than institutions or brands speaking for themselves. Trust hasn’t disappeared. It’s gotten personal. It moved from the billboard to the person you actually follow.

That’s the constraint and the opportunity in the same breath. You can’t buy your way into someone’s inner circle. You have to earn a seat in it, publicly, over time, in front of people who are watching to see if you’re consistent.

The irony… it has always been that way; humans trusted people based upon the context of that person’s place in the community, friend group, workplace, family group, sporting team, education, experience, knowledge, community contribution, and more.

Advertising, social media, and clickbait news have consumed and milked dry the value of their impact, as they race to the bottom, seeking shortcuts to success. They are in decline and have now been left hungry, wondering what to do next.

A few numbers worth sitting with

• Nielsen’s global trust research puts recommendations from people you know at the top of every trust category, well above any form of paid advertising, a gap that’s held for over a decade.

• Trust in traditional paid ads on TV, print and radio has fallen more than 20 percent since 2009, even as trust in online recommendations climbed.

• Edelman’s 2026 Trust Barometer found people increasingly unwilling to trust anyone outside their own values or circle, which means the bar for earning a stranger’s trust is higher than it’s ever been.

• The same research found people are nearly twice as willing to trust unpaid advocates, peers, and independent voices over what a brand says about itself.

Read those together, and the takeaway is simple. The old playbook, buy attention and hope it converts, is fighting the tide. The new one, earn belief in public, is swimming with it.

The framework: human connection over polish

This is where founders get it backwards. They think building trust means looking more professional. Cleaner logo, tighter copy, a polished LinkedIn voice that sounds like every other founder’s polished LinkedIn voice.

Trust doesn’t come from polish. It comes from being specific and being seen. Vulnerability is the actual mechanism, not a soft add-on. When you tell people what actually went wrong in your build, what you missed with your first customer, what keeps you up at 2am, you’re giving them something a brand can’t fake. Consistency over time is what turns that into belief. One honest post doesn’t build trust. Showing up the same honest way every week does.

Community is the delivery mechanism. A newsletter, a podcast, a comment section that people actually return to, these aren’t distribution channels. They’re where the relationship gets built. The audience isn’t just consuming your content, they’re deciding, episode by episode, post by post, whether you’re someone worth believing.

What you can do today

Pick one channel and go deeper before you go wider. Trying to be everywhere at once is how you end up nowhere with anyone. One newsletter, one podcast, one LinkedIn voice, done consistently, beats five channels done half-heartedly.

Tell the true version of the story, not the highlight reel. The founder posts that actually move people are the ones with a real cost attached. What you almost didn’t survive. What you got wrong before you got it right.

Show up on a schedule people can set their watch to. Trust is built through repetition as much as content. Same day, same format, every week, so people know when to expect you.

What it gives you

A trust asset does something a growth hack never will. It compounds. Every honest post makes the next one land harder, because the audience already has a reason to believe you.

It also changes who reaches out to you. Investors, partners, and customers who’ve been reading you for months show up already convinced, and those conversations move faster because you’re not starting from zero.

And eventually, if you build it the way Shetty did, it becomes something you can license. A trusted voice is a business asset, not just a marketing line item.

The case study: Startups Decoded

I built Startups Decoded the slow way. Eighty episodes in, we’ve crossed 850,000 downloads, and 10,000+ people show up every month for my editorial on Substack.

None of that happened because I ran ads. It happened because I told the truth about building companies, including the parts that didn’t work, and I showed up the same way every week until people started believing me before I said a word. That’s the whole strategy. There isn’t a second one hiding behind it.

That’s Shetty talking about his own evolution from guru to entrepreneur. But it’s really about the same thing every founder building in public has to reckon with. The version of you that shows up matters more than the version you’re performing.

The operating rule

Build the belief before you build the funnel, because nobody converts if you are a stranger.

If this hit, forward it to a founder who’s still trying to buy trust instead of build it.