Yes it is gendered feedback.

Yes it is real.

I’ve met with a few women founders lately who’ve brought the age-old question to me: “I’ve gotten XYZ feedback a few times, and now I think I need to pay attention. It feels gendered to me - I think I’m only getting it because I’m a woman. My (male) co-founder does the same behavior, and no one bats an eye when he does it. I’m not sure how I can lead if I can’t lead the way that’s authentic to me. What do I do with this feedback?”

XYZ is usually something like…

… When I give people direct feedback it hurts their feelings.

… When I think the work delivered is sub-par, my employees think I’m angry/ emotional/ overreactive.

… I don’t do enough to “build rapport” at the beginning of meetings. People think I’m all work and no fun.

This feedback can be painful to hear because while it is often gendered, there is always some kernel of truth in it. It if wasn’t true at all, it wouldn’t be painful - it would be easy to dismiss.

Earlier in my career I was working at Oculus as we were launching VR to the world. Oculus was a male-heavy company with a strong masculine culture. Pounding on tables to emphasize a point or physically towering over someone in a heated discussion were things that just happened. It was part of the culture. (It wasn’t a great culture.)

I was only two years into my product management career, but I had a significant scope of work - I led the product teams that invented the first virtual reality social platforms and created the retail demos used to launch VR to the world. In one of my performance reviews, I received some fairly gendered feedback that I dismissed out of hand because it was gendered. I was so angry at how sexist it was that I didn’t see the truth in it. I also didn’t see (until later) how sexist the culture was that enabled it. Because I dismissed it, I missed two crucial opportunities:

1. I missed the opportunity to learn that my behavior had a perceived impact in the culture I was existing in. People expected me to behave differently than I was, and there was a cost to that. Even though the behavior that was expected was fairly gendered (something along the lines of “smile more”), there was a truth that people felt less connected to me because of that. And as a product manager, people feeling connected to me is a key factor that enables success in the job.

2. I missed the opportunity to reflect on the context in which this feedback was offered. Any manager with an awareness of gendered feedback would have read this feedback from colleagues and weighed the tradeoffs of passing it along. My manager chose to deliver the feedback to me without this awareness, and without the ability to engage in a constructive conversation to help me make sense of it at the time. It was the first red flag signal of a culture that was, in my experience and many observations later, especially challenging for women. But since I dismissed the comment outright, I missed the clarity of that signal.

More than 10 years have passed, I’ve run my own company in that time and coached many women founders on the nuances of gendered feedback.

One of the crucial things to recognize when you are a founder receiving gendered feedback is the multiple types of power dynamics at play. When I was a relatively junior employee at Oculus receiving feedback from male peers and more senior/tenured/older male colleagues (all of whom held more power than I did), the “smile more” feedback was somewhat akin to “get in your place” (albeit, again, with lessons I could have learned but wasn’t ready to hear).

If I were to get that feedback now from people who report to me, I’d see it very differently because of how hard it is to give feedback upward based on the power dynamics at play. If I can fire someone, I have a lot of power over them. So offering me feedback when I am in the founder/CEO seat is a true gift, and one I hold reverence and respect for. I try to invite my ego to get out of the way so I can see the wisdom in the feedback that is offered.

A few years ago a peer coach offered me the feedback that she expected me to emote more. She offered it as a true peer and out of a desire to be feel connected to me. I had started to get curious about whether I was on the autism spectrum, and when I shared that with her, it all made so much sense to both of us. Diagnoses of women for autism often get missed in childhood because we learn how to mask better, and yet our masking still isn’t “good enough” for what society expects - hence the feedback I got at Oculus.

I offer this here because, while autism spectrum may or may not describe you, all humans exist with a range of behaviors and skills. You may have noticed up above that the examples I gave of the gendered feedback are all relational - people do expect women to behave differently relationally than men. Women are expected to be more compassionate and show their anger less. This is the reality of the context we live in, and as women founders, we get to choose how to relate to the feedback given that reality.

Some women founders, particularly technically strong ones who have grown their companies and found themselves managing teams fairly quickly may find themselves wanting to invest in improving the relational skills that are expected of them - and that are helpful for leading their teams well. This is something I work with my clients on in coaching.

Together we hear the feedback and pull out what can be learned from it and what parts of it need action (not all of it does). Sometimes it means there is a skill the founder needs to strengthen. Sometimes it means a team member isn’t a fit. Sometimes the culture needs to shift. We sort through it, I support the parts of you that might struggle to hear it or make sense of it at first, and then we game plan what’s needed. There is no one-size-fits-most approach to growing through gendered feedback, and yet it is something that many women founders face. If you ever want to chat about it, feel free to book a time. YC founders, check out the discussion on Bookface here.

I’d also welcome hearing in the comments from other women founders who have experienced this and what they learned/ how they grew through it.

Well, except we became profitable.

And yet stepping off the venture funding escalator was perhaps the best thing I ever did for our business and the thing that’s most likely to help it become the company it’s meant to be.

For the first time in a year, we’ve started to see growth turn positive. We’ve started to add new recurring revenue. We’ve shipped successful products for the first time. We have a team that loves working on the product, and for the first time since I replaced myself as CEO three years ago, I’ve actually had fun running the business.

For the first time in many years, I see a true future for the company. I didn’t let it go because I knew we were in a multi-billion dollar open space with little competition and we just needed to figure out execution. And as we’re figuring out execution, bit by bit, I am zooming out from the dots of the impressionist painting and seeing the whole picture. Wow. This is a fucking wild journey.

I often say I didn’t think we’d make it this far. I got into YC! Holy shit! I raised millions of dollars! Woah. I built a product people actually use?! Wow! (Sometimes, I see links to my product other people send to group chats and I’m shocked people are actually using it.) I run a profitable company?! What?!!!

I never could have imagined the awe I’d feel when the final dots started to be dropped into place and the painting was indisputably beautiful. I never could have imagined we’d make it this far and be this successful.

I also never could have imagined how insane this journey would be. I lost my physical abilities and became disabled for a while, I may have lost my fertility, and I’ve definitely lost my sanity for a bit. And I’m so incredibly grateful for all of the hard-won lessons that come along the path of being a founder. My god this work is hard.

I’ve lived it myself, left, and (like a masochist) came back. Along the way I started coaching other founders to help them on their journey. I love that work often more than I love running my own company, which is why I do both. I get to ride their journey with them and help smooth the rough edges - it’s such a wild privilege to be alongside them. I get to help them find their reasons for doing this work, I support them as they discover their own hard-won lessons, and I’m there to celebrate their successes and coach them to new heights.

If you are looking for coaching support on your journey, I have one spot open in my coaching practice.

Reach out for a discovery call: lunarayemail@gmail.com.

I had just finished a 360 review with her team of her leadership, and as she listed her complaints about her company culture, I could immediately see how she had unknowingly created it.

She asked me to share examples of how. I went through my notes from my conversations with her team and read some of the quotes out loud. They were painful to hear. Words like “micromanager” and “doesn’t trust the team” abounded. “She lashes out at the team when she hasn’t processed her emotions.” It was the first time she was hearing that feedback, and it stung. But she’s one of my most resilient clients, and I knew she could handle hearing it, as painful as it was.

Culture always comes from the top. Culture is not what we do as a company, it’s how we do it. It’s what it feels like day to day to work here. A high anxiety culture always points to a founder (usually founder CEO) with a lot of unmanaged anxiety. A high blame culture points to a founder who doesn’t trust their team. A “fly by the seat of our pants and ship whatever we feel like it” culture points to a founder who leads that way.

Whenever founders notice a culture that they don’t like, they need to look in the mirror at themselves. That can be really hard to do.

The interesting thing is that the way we lead is also behavior we learned. Most of it we learned from our parents or early caretakers, but some of it we learned from bosses or mentors in our career.

Anger was a common theme for my client, and when I asked her about her anger and who she might have learned that from, it was from her mother. Her mother’s unprocessed and unmanaged anger impacted her every day of her childhood. And then she realized that her own unprocessed and unmanaged anger was having the same impact on her team.

Together we did an exercise to help her feel and process some of the anger towards her mother to help it move and release. Adjacent emotions like sadness, shame, and guilt for propagating this experience to her team came up, and we welcomed those as well. We closed with a few deep breaths to bring a positive sensation into her body, ground, and re-regulate her nervous system.

And then we spoke about what comes next.

It’s clear to her her culture needs to change. And now it’s clear to her that she’s the one that’s created it as it is, and she needs to take ownership for changing it.

We talked about what to do to turn her culture around. Here was my advice:

1. Acknowledge what the culture is and take accountability for the fact that you created it. Acknowledge the challenging impact it has had on the team. Help people feel seen in their difficult experiences as a result of the culture.

2. Create a task force to help shift the culture. That task force should include a few senior leaders you are really willing to listen to and a few ICs from different functions, since people at different levels of seniority experience culture differently. Meet weekly with those folks: work with them to articulate the culture as it is today and to describe how you want to shift it.

3. Articulate a vision for the culture that you and your task force are completely in alignment on. Share that broadly within the company.

4. Create a plan with your task force to shift the culture and hold you accountable. Create mechanisms for people in the company, and particularly the task force, to let you know when you’re steering off course from the intention.

5. Work with outside support on the hardest growth edges for you personally. If anxiety, anger, fear, or other challenging emotions have been part of your life for a long time, the right therapist or coach can help you learn how to move those emotions skillfully and reveal the wisdom underneath them.

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If shifting your company’s culture is something you’d like to talk about, feel free to reach out. I’m currently offering complimentary 1-hour coaching sessions to up to 3 YC founders who reach out before the end of the month. Grab time here or reach out: lunarayemail@gmail.com

My work is informed by my time at Meta, Instagram, Oculus, and Faire, and from running my own YC company (Plura), as well as the dozens of founders I’ve supported as a coach.

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They have a shared reality problem.

Work is happening. People are trying. Everyone’s doing their best version of “moving fast.” And still: projects drift, timelines blur, growth becomes a blur of activity, and the founder ends up carrying an invisible job called making sense of everything.

When people say “we need more accountability,” they often mean one of three things:

• “I don’t actually know what’s going on until it’s already late.”

• “I don’t feel like we’re learning as fast as we could be learning.”

• “I keep getting surprised by what we built / shipped / spent time on.”

The fix is almost never “more pressure.”

It’s almost always more clarity earlier.

And the simplest way I know to create that clarity is:

Write the plan. Review the work. Repeat.

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The eggshell rule: catch bad decisions early

There’s an old analogy from High Output Management that I love:

If you’re running a breakfast kitchen and a piece of eggshell falls onto the griddle, the best time to catch it is immediately.

The worst time to catch it is when the customer bites into their eggs, crunches eggshell, and now you’re comping the meal, apologizing, and losing trust.

Startups do the same thing.

The “eggshell” is the poor decision, the unexamined assumption, the unclear scope, the “wouldn’t this be cool?” detour.

The “customer bite” is when it ships, breaks something, annoys users, or creates a new surface area you now have to maintain.

Planning docs (or even lightweight written plans) are how you catch eggshells before they hit production.

Growth experiments: the weekly cadence that changes everything

When I led the User Acquisition team at Instagram growth, every growth team had a weekly experiment review.

Not fancy. Not bureaucratic. Just relentlessly consistent.

I wish more early-stage teams would steal this.

Why it works

A weekly experiment review does three things at once:

1. It spreads learning

   • Everyone sees what’s running and what worked

2. It creates accountability

   • If you have to report back next week, you think more clearly this week

3. It forces hypotheses

   • You can’t “review” a thing if you never decided what success means

It also solves a classic founder complaint:

“They’re doing a lot, but it feels random.”

Often that “random” feeling is just missing structure:

• no opportunity sizing / impact estimate

• no stated hypothesis

• no success threshold

• no time box

• no written record of what was tried

Weekly review fixes that without slowing speed.

The simplest experiment tracker (that still works)

You do not need a fancy tool for this.

The “most advanced” tool many top growth teams use is… a doc or spreadsheet.

Here’s a starter template you can copy into Notion / Sheets / Airtable.

• Experiment name

• Owner

• Hypothesis (one sentence)

• What we’re changing (the variable)

• Success metric (one metric)

• Success threshold (the “if we see X, we keep going” line)

• Start date

• Next review date

• Time box (how long we’ll run it before deciding)

• Current results (updated weekly)

• Decision (continue / iterate / stop)

• Learnings (what we now believe)

And then structure it into three sections:

• Running

• Queued

• Archived (with learnings)

That’s it.

If you do nothing else: require a success threshold.

Because “we launched a podcast” isn’t an experiment.

It becomes an experiment when you say:

• “We’ll run this for 4 weeks.”

• “If weekly listeners exceed 300 and we see at least 5 demo-intent inbound mentions, we continue.”

• “If not, we stop or redesign.”

Experiments need a hypothesis and a finish line.

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Engineering planning: where speed actually comes from

Here’s a thing founders learn the hard way:

The fastest teams don’t skip planning.

They skip unnecessary planning.

They do just enough thinking up front to avoid expensive rework later.

A lot of engineering accountability problems are actually scoping problems in disguise.

When the scope is fuzzy, two failure modes happen:

• engineers run off in a “weird direction” (despite best intentions)

• initiative that isn’t aligned with product/customer impact (founders only discover misalignment once something is already built)

Here’s the core move:

Make “plan first” the default

Especially for multi-day work.

For multi-day work, there should be some version of:

• What are we building?

• Why are we building it?

• What are we not building?

• How will we know it’s done?

This can be bullets. It can be a few paragraphs. It can be a ticket comment.

But the point is: it becomes reviewable. You can catch eggshells before they ship.

A useful framing for founders:

• For junior folks, you do more scoping.

• For senior folks, they do the scoping — but you still expect a plan.

But at every level, there is still a plan. Even “senior” doesn’t mean “YOLO into production.” It means: “I can think this through, write it down, and get alignment quickly.”

The goal isn’t to add process. The goal is to shift thinking earlier, where changes are cheap.

Because again: eggshells.

The takeaway: “Make them plan” is kinder than constant escalation

If you take nothing else away, take this:

1. “Hold people accountable.”

2. “Make them plan.”

And I want to underline something:

Requiring a plan is a kindness.

It reduces:

• surprise

• rework

• resentment

• “why the hell did you build it this way?”

• and founder whiplash

It also makes it dramatically easier to lead without becoming a micromanager, because you’re not policing execution - you’re shaping intent.

How to implement this

If you want to implement this with minimal overhead, here’s a clean rollout:

Week 1: Make work visible

• Create one tracker:

  • either “Experiments” (growth/outbound) or “Projects” (engineering/product)

• Add 5–10 items that already exist

• Add owners + next review dates

Week 2: Start weekly review

• 30 minutes, same time every week

• Agenda:

  1. What shipped / progressed?

  2. What are the metrics right now?

  3. What are we learning?

  4. Any blockers?

  5. Any experiments/projects to kill?

Week 3: Add success thresholds

• Require every new initiative to define:

  • hypothesis

  • success metric

  • success threshold

  • time box

Week 4: Tighten scoping

• For any multi-day eng work:

  • short written plan before implementation

  • founder/product reviews plan, not code

This is enough to create a huge step-function improvement in accountability without introducing Big Company theater.

If you’d like support implementing better accountability for fewer surprises with your team, this is something I coach founders on as an executive coach. Reach out for a discovery call: lunarayemail@gmail.com.

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When I started my company, my conscious reasons were:

1. I always knew I wanted to start a business. Running your own business was a multi-generational tradition in my family. Because it was valued in my upbringing, I always knew I’d do it too.

2. I thought long and hard about product-founder fit and realized the place I’d have the most product-founder fit was in social products after 5 years at Meta. When I explored specifically what I wanted to build, I saw that the non-monogamous and queer communities I was part of were underserved by the mainstream social platforms, and I thought I could serve them better.

After several years of running my company and stepping down due to burnout, I realized my subconscious reasons for starting it were:

1. I had experienced deep loneliness as an only child and (probably) autistic teenager. I didn’t understand how to connect with people for many years of my life. And while I felt the loneliness through most of high school, I didn’t learn how to “fix” it until college at MIT, where being neurodivergent was pretty normal.

2. The pandemic triggered my loneliness - as it did for many people. I went from feeling an abundance of community to realizing I was at a place where I had very few close friends, despite a decade of living in the Bay Area. I missed spending time with people at community events and wanted to make that possible again.

Essentially, a sense of lack triggered my subconscious motivation for creating my company, Plura. I was running away from loneliness and wanting to “solve” it with an app. Somehow, it worked.

When I unexpectedly needed to relocate cities to San Diego for my partner’s job after 14 years in the Bay Area, I was devastated to leave behind 14 years of dear friendships and community.

But, what I saw on the other side of that was how much I had learned through years of running Plura, studying how people build relationships and community, and learning alongside folks who were masters of community building. In the few months from the time I started living in San Diego part-time to choosing to move down fully, I found my people so quickly through Plura that I was able to hold a birthday party for myself with new friends in San Diego while my belongings were on the truck on their way down. I felt a deeply connected sense of community and incredible gratitude that I had found my people so quickly, completely in awe of how this was even possible.

The product I had built had worked for me - it had solved my own problem.

After fours years of running Plura, I burned out and replaced myself as CEO.

Two years later, I came back. Since stepping back into the CEO role 8 months ago, I struggled to re-find my motivation for leading the company. The original source - a sense of deep loneliness - is not something that’s present for me anymore. And I’d rather run a company off of an inspiring vision instead of a sense of lack. I’m finding that vision again.

Human connection is a lifelong practice.

Throughout our lives, we move cities and lose friendships. Romantic relationships end or transition. Loved ones die. That is part of being human.

The ability to cultivate new connections is deeply foundational to being human. We need people in our lives for fun, for support, for co-regulation, for leaning on when times are hard, for offering a hand when they need help, and for love. And yet, it’s something so many people struggle with.

As I recommit to my company for the next decade, I’m choosing to step into a vision of abundant love.

Abundant love in all it’s forms - romantic, sexual, platonic, friendly, compassionate… the list is infinite.

Plura exists to help people connect to abundant love.

In addition to running Plura, I also coach founders. My practice is full at the moment, but if this work speaks to you, reach out and I can let you know when I have an opening. I offer complimentary coaching deep-dives to YC founders when I can. lunarayemail@gmail.com

And then we both burst into laughter.

I was sitting across the table from an ex-founder who had successfully IPO’d his company and did have significant resources to invest in my company.

We were each playing a role in a “persona” dinner at a founder retreat hosted by Dave Kashen. Each of us had been tasked with stepping into a persona that was far from our usual identity in order to learn what could be found from exploring the edge of who we thought we were. He had been invited to act like the douchebag he was very far from, and I was invited to “show romantic interest in every person there” (with consent).

When I’m invited to play at the edge, I rise to the challenge.

Over the next 10 minutes after my opening line, we collectively conspired to create a deal that was absurd both for how wild it was and how it pointed to something so unspoken in Silicon Valley that all we could do was laugh. And for me, it was deeply healing.

One of my great fears as a founder that never happened was being hit on by potential or current investors. I had heard stories from other women founders who had experienced this. I was running an explicitly sex-positive company serving non-monogamous communities, and I thought investors would interpret that in a way I didn’t want them to. I had been inappropriately propositioned in almost every job I’d ever had and from MIT professors. Before fundraising, I experienced a lot of agitation and distress by anticipating the fear of what might happen. And it never did.

Getting to step into that fear directly and play it out was incredibly empowering and healing. The deal we “arranged,” though absurd and fantastical, is perhaps a deal I might have taken with the right energy. I joked in our banter that “everything has a price.” And while that deal was imaginary, getting to explore it from a place of empowerment helped me release the last remaining dregs of the fear.

My YC company is profitable, so we’ll never again be reliant on prospective investors who may or may not want additional benefits for their investment. I’ve also shied away from fundraising out of fear of investors having control and exerting that for whatever additional benefits they want. Was this fear real? Well, all fears are. Whether it will happen or not is beside the point.

Releasing the fear creates choice. Optionality. If I’m not afraid of investors making bonus requests as part of their investment decision, I have more choice as to whether to raise money or not.

As founders, we’re all running fears on a subconscious frequency in our psyche, and they affect every decision we make and the way we run our business. Bringing them into the light can allow us to understand them, get curious about them, and release them, so that we have more opportunity to make different choices than the patterned cycle of decisions that led us here.

If you want explore your underlying fears to create more space in your decision-making, this is something I coach founders on as an executive coach. Reach out for a discovery call: lunarayemail@gmail.com.

There is some part of me that wonders if I really want everything that comes with a million dollar coaching practice and a massively successful startup. I look at the people I know personally who have those things, and don’t see their lives as any better than mine in the moment, and certainly not better along the dimensions that I’d expect might change if I had those things.

When I really think about being pregnant for any longer than half a second, there are so many aspects of it that completely squick me out.

I just completed a coaching training program where the mantra of the weekend for me was “appreciation of the present state.” One of the core beliefs in this modality is if you are working with a client and they tell you they want something they don’t already have, you can simply recognize that there is some part of their body system that doesn’t actually want that thing yet.

There is intellectual agency - I want that thing because I think I should have it - I see other people have it, because I’m told by my peers/my parents/society that it’s the right thing to want, or because it seems like a good thing to have. And then there is somatic agency - I want that thing with my whole body, every part of me wants it, and no part is hesitating.

Weirdly, while we’d like to think we have control over our wants, we actually don’t have control over our deepest desires. In the wise words of professional dominatrix and Daoist nun Kasia Urbaniak, “We what we want.” Everything that’s happened in our lives - and many things from before our lifetimes - converge to create those wants for us. And when we can surrender into them, we can actually welcome in what we most want.

One of the elements of this weekend training program is we rotate through becoming a “subject” and “surrending” our coaching business to a new CEO (one of the other coaches) who helps us unlock what we most want through the course of the weekend - typically focused on how to uplevel our coaching business and get new clients. As a subject this time around, I couldn’t even figure out what I wanted to ask for - it wasn’t clear to me that I actually wanted new clients despite the fact that I should want new clients (running a startup and a coaching business is kind of a lot). I set my intention to figure out what was next for me with both businesses and life.

Instead of doing the things I was “supposed” to be doing to get new clients, I ran off into the trees. I’ve been really missing the beautiful redwoods of the Bay since moving to San Diego, and our retreat sanctuary was set on the base of Mount Tam. I really wanted trees. I needed trees.

Along my first hike, I “accidentally” took a wrong turn and only noticed it when I’d gone so far, I’d be 30 minutes late for the training if I turned around immediately. But the trees were so beautiful and my curiosity to continue on the path I was on was so strong, so I just followed my curiosity.

And as I ran along, some other hikers ran by me in a conversation.

Dude 1: “It’s great, I finally feel like I’ve gotten the old JD back.”

Dude 2: “Oh really, how so?”

Dude 1: “He said to me, I don’t know what I’m doing next. But for the first time in my life, I’m giving myself until the end of the year to not know.”

Overhearing that, something just hit for me. I don’t know what I’m doing next. Is my focus the coaching business, the startup, or building a family? (For those who have been following along, the family piece was been delayed for me while I waited for a clear biopsy of my pre-cancer diagnosis - which I got a few days ago!)

The reminder that I can just accept the not knowing provided so much peace. And that I can not know until the end of the year, and it’s fine.

And as I started to just appreciate the present state - two businesses, soon to be a third (yikes), a who-knows-what-the-future-brings pre-cancer diagnosis, a beautiful home near my parents who I love dearly, a loving, supportive how-did-I-get-so-lucky husband, the most incredible friends and community across two cities - a new level of peace settled in.

I don’t have a billion dollar startup right now because I don’t actually want to be the CEO of one right now. I don’t have a million dollar coaching practice yet because it’s unclear how my life would be any better if I did. I love the clients I already have. And I’m not pregnant yet because I don’t actually want to be (that one is really hard to write “out loud”).

One of the mental models I’ve come to associate with appreciating the present state is the recognition that when I deeply want something and every part of me is lined up with that want, I’ve always gotten it. If you think of all the parts of you that could want something as vectors pointing in slightly different directions - because they want slightly different things - and you add up the sum of those vectors, they point in a direction with a certain magnitude. But when all the parts align in a single direction and you sum them all together, they become unstoppably powerful.

So what do you really want and why don’t you already have it?

I wrote this post in July 2025 but waited until now to post it until I had more space to support other founders. I now have space to support other founders with coaching. If you know what you really want and want to explore why you don’t already have it, feel free to reach out lunarayemail@gmail.com with subject line “what I want.” I’m currently offering complimentary coaching deepdives to up to 3 YC founders.

Do any of these feel familiar?

• Your day disappears into Slack, meetings, and quick tasks — but the big stuff never happens.

• You struggle to make time for strategy, new growth channels, or building functions that don’t yet exist.

• You’re constantly context switching and end the day exhausted but unfulfilled.

If so, you’ve hit a founder skill gate. On the other side is leverage, clarity, and compounding progress — but only if you learn to actively manage your time and priorities.

The Core System

To consistently do your most important work, you need three simple practices:

1. Weekly Planning

• Pick a consistent time. I like Fridays.

• Review company metrics and your quarterly OKRs.

• Identify the 5–10 highest-leverage tasks for the upcoming week.

• Right-size the list so you actually complete it — momentum matters.

2. Daily Planning

• Choose your top priorities before opening Slack or email.

• Make a short list you’re 95% likely to complete.

• Check things off. That sense of progress is fuel.

3. Time Blocks for “Important But Not Urgent” Work

• Protect 2–3 hour blocks every week for deep focus: strategy, vision, product innovation, growth experiments, AI planning.

• These blocks are where you create future value. Without them, you stay stuck reacting to the present.

What Happens If You Don’t Do This

Your day defaults to reactive mode:

1. Open Slack

2. Go to meetings

3. Answer messages

4. Squeeze in small tasks between calls

Result: the game-changing work never happens — not because you’re undisciplined, but because you’re using Slack and email as your to-do list. The loudest voice wins, not the highest-leverage work.

Start With One Block

Even one protected two-hour block a week will change your trajectory. You’ll crave more. And you’ll realize that much of what falls off your plate… didn’t matter anyway.

Want Help Building Your System?

Every founder has a different working style. The frameworks are universal — but each implementation is personal.

I have one open coaching spot. If you’re a YC founder and want to build a system that guarantees you’re working on the highest-value thing every week, reach out with with subject line “slack”: lunarayemail@gmail.com. Right now I am offering complimentary coaching deepdives to up to 3 founders.

Learn more about my coaching here.

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Some plants will turn their heads dramatically within days. Others will take years to noticeably shift towards sunlight.

Where is your sunlight?

The things we put our attention on inevitably grow. If you focus on one friendship over others, you’ll deepen more quickly with that friend than with others. If you focus on one part of your business over the others, that will be the part that will be more likely to grow.

One of the patterns I often see amongst the founders I coach is a tendency to do the things we think we should do for our business because we see other founders doing them. Or we hear from our investors we should do them. Or (this is so common) the YC partner told us to, based on a short conversation with limited context on the business and the founder.

And we contort ourselves in these ways where we stop doing the things we love and we start doing the “shoulds” and then we lose sight of the reason we started this in the first place. Because we liked it. Because it was fun.

Starting a company is hard enough. You can do it in extra hard mode, where 80% of your day you force yourself to do things you don’t enjoy doing and where you live in a state of heightened anxiety, stress, cortisol, and/or fear, where every decision seems life-or-death, where everything has so much weight. Or you can do it in just basic hard mode, where you do the hard work of starting a company, but over time you find people who enjoy doing the tasks you hate, and you get to spend more and more of your time on the things that bring you joy. Finding joy in your work is a choice. It’s your choice.

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When I see founders really struggling (and wow have I been there), I ask them what would make this just 5% more fun. What could we do to introduce just a little bit more joy into your day?

Were you a deeply technical software engineer who found himself a CEO and miss the fun of getting to hack on the next product? Ok, block out some time on your calendar and go do that. Did you used to spend more time with your friends and family, enjoy traveling, love laughing and playing, and find yourself without enough time to do those things? Make changes. Go do those things.

It’s actually quite simple.

When founders are at the end of their rope, every action feels like pushing a boulder uphill, and even the easy tasks seem hard. Find a way to cultivate more joy.

Right now I am offering complimentary coaching deepdives to up to 3 founders. Reach out with the subject line “Joy” to lunarayemail@gmail.com.

Learn more about my coaching here.

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I was a product manager and product lead before I became a founder. I led User Acquisition at Instagram from 700M → 1.1B people, I launched consumer social VR for Oculus, and I led the marketplaces team at Faire. My product philosophy comes from this experience, and from what I learned when I applied it at my pre- and later post-PMF startup, Plura.

There are a lot of ways to write product specs (or product requirements docs - PRDs), and I don’t think there’s any universal format that’s objectively better than others I’ve seen. I’ve developed one that’s worked for me which I share below and link to some others from Lenny Rachitsky.

But before that, here’s some philosophy behind what the purpose of these docs is, and how they tie into the product cycle.

Purpose of product specs

The purpose of product specs is to get the whole team on the same page about what you are building. The most expensive time to change a feature is after the product has already shipped.

I’ll say that again for those in the back - the most expensive time to change a feature is after the product has already shipped. The book High Output Management uses a restaurant kitchen analogy. The most expensive time to catch a piece of eggshell in a breakfast of fried eggs is when the customer takes a bite and discovers egg shell. Gross! Full refund + a negative review. The least expensive time is when the egg gets cracked onto the griddle. Catch your eggshells before they go to their customers. Write product specs.

The least expensive time to change a feature is when you’re writing the product spec. Your teammates can’t read your mind, so if you have specific opinions that you want to see come to fruition in the product, you should include them in the product spec. Verbally stating these without writing them down is a recipe for miscommunication. This is the time to engage the whole team in feedback and discussion.

Product cycle

Product specs come in during a particular phase of the product development lifecycle.

1. Gather customer feedback (and share it with your team)

2. Write a product spec

   1. Then, get team feedback and iterate

3. Design the product

   1. Then, get team feedback and iterate

   2. This is also a good time to write engineering specs. Even if there is only one engineer, scoping out the engineering work in a doc with specific tasks can help the engineer think through the pieces of what needs to get built and offer options for design tradeoffs.

4. Create the engineering tasks

5. Build the product

   1. Then, get final design and product sign-off + bug testing

6. Ship and measure impact

Length / detail

You want product docs to be specific enough to communicate the key information so that there aren’t major surprises farther along the product development process, and you want to keep them a wieldy length so that they are useful for collaboration. Again, your teammates can’t read minds and none of us have perfect memories; writing things down reduces confusion later.

Components

The exact format doesn’t matter too much, but most product docs should have most of these components.

1. Context

   1. Why are we building this product/feature?

   2. What have our customers told us they need?

   3. Is there anything else the whole team should know about why we’re doing this?

2. Metrics / goals

   1. What are we trying to achieve by building this product?

   2. How will we know (measure) if we achieved that?

   3. What instrumentation / logging / analytics will we need to set up to measure that?

3. Key features / flows

   1. I tend to think in terms of user flows, which can also help designers in their process. E.g., what is the first thing the user does, second thing, etc.?

   2. What are the edge cases we need to think about and specify behavior for?

   3. Which features are within MVP and out of scope for MVP? I like to include one section that’s MVP, and one section called Vfuture where we can put all the great ideas we have that we aren’t going to build right now.

4. Open questions

   1. What does the team still need to answer? What’s our plan for answering those?

Examples

Product spec: Publish to Eventbrite

Product spec template

Lenny Rachitsky also did a great writeup that includes links to many PRD templates.

When to start using product specs in a company’s journey

The best time to start using product specs is the moment you start your company. It’s simply an exercise in clarifying your thinking and getting the whole team (even if that’s just you and an AI) on the same page.

I see a lot of early stage founders not writing product specs because they think it’s faster to just build what’s in their head. But as long as there is human to human communication happening in order to build and deliver the product, having the details written down will save so much time later. The cost of a feature built incorrectly or a miscommunication that results in a cofounder disagreement is so much more expensive than the relatively short amount of time it takes to write these. And, you will build a better product when you get the full input of the team at the product spec and design phase (vs after it’s shipped).

If you’re a founder coming from an engineering or non-technical background and you’d like to jam on product specs, right now I am offering complimentary coaching deepdives to up to 3 founders until Nov 10th. Reach out to lunarayemail@gmail.com and mention product specs.

Be coached by a founder who gets it

Founding a company is hard - I’ve been there. Sometimes you just want to sprawl on the floor - what do I do next? In those moments, having support from someone who’s been through it before can make all the difference. As a former YC founder turned founder coach, I get what you’re going through and can help you think through your hardest problems, up-level your skills, and come out successful on the other side.

Topics founders work on in coaching

• Transform culture into AI-first - shift the mindset of your team to think AI-first with every process and product, and operationalize this across the company to compete with AI-native companies coming up behind

• Build systems & teams that scale - create the operational, product, and organizational practices that take you from PMF to A, B, C and beyond

• Scale yourself to lead your scaling company - understand your blindspots and gain the skills you’ll need to take your company to the next stage

About Luna Ray

• Luna Ray is the founder and Chair of YCombinator-backed Plura, the social app for edge-of-culture communities, where she raised multiple rounds of venture funding and built Plura into a profitable business

• Luna led User Acquisition for Instagram when it was the fastest growing app in the world (700M → 1.1B people)

• She led led the marketplace org at Faire and is a former consultant at Bain & Company

• She has two MIT degrees in business and engineering

• Luna has trained in six different coaching modalities, including IFS (Internal Family Systems / parts work) and Pain Reprocessing Therapy (for chronic symptoms)

About Luna’s approach

• Deep empathy: As a former YC founder, Luna gets what it takes to be in the trenches day-in and day-out

• Learn the best practices from Instagram product that Luna road-tested in her YC startup and proved effective at all stages

• Receive direct feedback and ongoing accountability in your growth process

• Get feedback from someone who’s “been through it” - an empathetic sounding board to hash through your current biggest problem

• Help you see around corners and avoid common scaling mistakes

• Gain access to your inner intuition for better decision-making and deeper conviction

• Break through team tensions and build deeper, stronger relationships with your team

• Grow the “you” product so you can grow your company

Exclusive YC Offer

• Limited time enrollment period until Nov 10th

• Complimentary 60-minute coaching deepdive for three founders who sign up before Nov 10th

• Bring the hardest problem you’re facing right now and come out with fresh ideas and a sense of relief and greater ease

• If you are seeing this after Nov 10th, 2025, reach out to learn what’s available

How to redeem

Email Luna Ray at lunarayemail@gmail.com and mention “substack coaching post” in your email.

Do you feel like…

… Your day gets away from you and you aren’t always sure that you did the most important things?

… You’re struggling to find time for longer term planning and strategy work or creating and building out new functions that you don’t have yet (e.g., growth marketing)?

… You feel like you’re constantly context switching and being pulled in a million directions by your team, and you’re not sure which way is up?

If so, you’ve got yet another founder skill gate to clear in front of you. And the good news is: the skills you develop to pass through that gate will make your life much better on the other side.

As a founder, I learned these skills by trial and error. I noticed that I felt exhausted at the end of each day but wasn’t accomplishing as much as I could. Month after month I reflected on the way I was managing myself and designed a system to optimize for my own productivity.

The most basic high-level requirements are:

1. Weekly planning for your own work that’s tied to company metrics/goals and any personal OKRs.

2. Daily planning that assesses what you intend to accomplish that week and what you’ll do today.

3. 2-3 hour calendar time-blocks for the “important but not urgent” work that always slips.

When I meet founders who aren’t doing these things, their day usually looks like:

1. Open Slack and respond

2. Attend meetings on the calendar

3. Check Slack and email between meetings and unblock people

4. Fill in the gaps between meetings with smaller projects that can be done in 30-60 mins

The deeper work that requires 2-3 hours to really get into never happens. This means they miss out on accomplishing some of the most important work: setting strategy and vision for the company, figuring out their AI strategy, opening new lines of business or growth channels, inventing a new product based on customer feedback, planning a detailed roadmap for the quarter, etc.

Founders will often have a sense they should be doing these things but don’t know how to get there.

If this is you, you are likely using Slack/email as your to-do list. This means that your priorities are directed by your team and customers - and you’ll be responsive to the loudest voice. The loudest voice isn’t necessarily calling you to the most valuable thing to spend your time on.

Let’s say you want to unlock a new growth channel but you haven’t hired for it yet, so your task is to do the work to figure out how to set up that new channel. If your day-to-day is responding to Slack messages, emails, and fixing whatever is most broken, well, that means you’ll never get to the growth work. Clearly that’s a problem.

So let’s talk about how to fix this.

Weekly planning

Find a time each week you can consistently do weekly planning. I like to do it on Fridays. I’ve done it either Friday afternoons before I sign off, which works when the planning is lighter-weight and takes me only ~10 minutes, or Friday mornings first thing when the planning is more extensive and needs to involved more than just my own work plan (e.g., takes 30-60 mins, if I’m also using that time to check on dashboards and metrics and plan for the team). Some founders already do team planning right before their Monday morning team sync; if you are already planning for your team then, adding your own planning at the same time should be easy. It doesn’t matter when it happens.

Add a time block to your calendar to remind you to do this.

The time you do your planning is the right time to check in on company metrics and your personal quarterly OKRs. Are there things you need to do this week to remain on track to accomplish your quarterly OKRs? Add them in. (For brevity, I’m not going to cover OKR planning here, but feel free to contact me if that’s something you’d like to chat about: lunarayemail@gmail.com.)

The output of your weekly planning should be a list of tasks that you plan to do in the following week. You should attempt to right-size this so you accomplish all of them almost every week. The reason for that is it feels really good to accomplish your to-do list.

Daily planning

Again, consistency here matters. Pick a time each day to select your to-do list for the day. I like to do it first thing before I open my computer (I keep my to-do list on paper like an old school millennial). For other founders, the best time of day to do this is the end of the day when they’ll prep for the following day. Other founders like to do it at a consistent time the afternoon before, either lunchtime or 3 PM, as examples, since the end and start of each day can be rushed. Again, add a time block to your calendar if that will help you remember to do this.

The output of your daily planning should be an ordered list of tasks that you can go through as you have time in your day. Check off your tasks as you go. It feels good. You’re aiming for a volume of tasks that you can fully complete in the day 95% of the time. Because it feels good to do that.

Time blocks for important but not urgent work

Each week when you’re doing your weekly planning, put time blocks on your calendar to accomplish the bigger projects that require uninterrupted 2-3 hours of time to make significant progress on.

When I was a seed-stage solo founder and the only product designer on my team, I learned that I needed time to do this work before my team started pinging me on Slack, so I blocked off Wednesday mornings every week and moved standup to be async the evening before. On Wednesdays I’d wake up and sit at my computer in my PJs and jam on design before my team got going.

I’ve seen founders block off half days or full days once a week for their own IC work - whether that’s planning, strategy, new projects, or other important but not urgent work that might change the trajectory of the company but will never get done if it isn’t given a protected home. Another approach is blocking off the first two hours of every day for this work.

Start small - even just one two-hour block a week will make a noticeable impact. Once you have these, you’ll want more of them. And you’ll find the other stuff still gets done, and whatever gets dropped didn’t need to happen anyway 🙂.

As I’ve worked with founders as their coach, I’ve learned which elements of this system are universally valuable, and which parts need to be customized to each individual based on their working style and preferences.

My coaching practice currently has one open spot. If you’re wanting to talk more about maxing your productivity, reach out to me at lunarayemail@gmail.com.

Way back in the day we cared about food for survival, so we made stone tools that helped us kill and skin animals and grind plants into consumable forms. Today, the AI technology we build and how we build it reflects our values.

With AI advancing at unprecedented speed, there has been been a time in human history when technology has so rapidly shaped our collective future.

As a CEO pivoting my own company towards this AI future, and as a founder coach working with other founders on their own AI transformations, I think a lot about what values we want to imbue into the technology we create and how we run our businesses.

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One of the unique circumstances about this wave of technology shift is the degree of fear that it’s been met with. So many founders I speak with talk about how incredibly impactful AI has been on the areas of their business that have chosen to learn how to work with it - most often the software teams - and yet how reluctant the other areas have been to even give it a try.

There is so much fear. That fear is felt amongst engineers, who are rapidly seeing the unique role they used to play within companies be replaced overnight. That fear is felt amongst managers who don’t know if they can promise jobs to their teams in the future, or if their own role is even safe. That fear is felt amongst the individual contributors across sales, customer support, operations, finance, and every other function, who see AI rapidly moving in on areas of their expertise that they developed many years accumulating.

That fear is valid.

As founders, we must meet fear with leadership.

Leadership here isn’t about “power over” - telling someone what to do or how to do it. (”Just learn how to use this new AI tool and your job will be so much easier! You’ll have more time to do… MORE WORK!”)

Leadership here is about listening. About hearing all the fears. About compassionately responding.

Leadership here is about leading with vision and values. What will our company look like in five years? What role will AI play in our future? What will that mean for the people who are employed by us today? What are the values we have as a company that will guide those decisions?

What are your values?

How will you steer your ship into the future with those values?

How will you transparently and honestly communicate those values to your team? (Assuming transparency and honesty are part of your values.)

I’ve already seen so many different approaches to answering these questions. None of them are right or wrong, better or worse.

I’ve seen some founders say to their teams: “the job you had doesn’t exist anymore here. You are still employed, but it’s for a new job. And that job includes AI as part of every workflow and every system. Those are the new expectations for your job. If that doesn’t work for you, this isn’t the right job for you.”

I’ve seen other founders say: “this AI thing is scary. It scares me too. It’s also a tremendous opportunity for our business. I am deeply committed to the people who work here and I plan to build AI around the people who already work here. I promise that if AI “takes your job” and we lay people off due to AI, that will be my last day of employment here as well.”

And I’ve seen other founders say: “we don’t totally know what to do with this AI thing yet in our company, but we want to play and explore together. So every few weeks, we’ll do a company-wide hackathon, where anyone can work on any project they want to - company-related or not - and then we’ll ‘show and tell’ those. And we just think that if we let everyone play, we’ll find good ways to incorporate AI into our business over time.”

Each of these approaches has merit. Each of them has values embedded within it. The first is a capitalist-leaning approach that’s aligns with the fiduciary duty founders have when they raise money from VCs. It’s a capitalist winning mindset.

The second approach is a people-first approach, with deep loyalty to the team. Even if the business could survive longer or “make it through” a crunch period with layoffs, these founders are committed to the people who followed them on the journey. There’s a beauty in that.

The last approach is fun and playful. It accepts that we don’t know the future or how AI will impact things, and doesn’t declare anything about the safety or lack of safety of the jobs of the team. It focuses on the present moment and what we can learn as we play. It mimics the way children learn - through play.

Again, there is no single right approach, and anything you choose as a founder will be a reflection of your own values. And it can shift over time.

In my own experience as a founder, I’ve shifted between these. I leaned heavily - at times too heavily - in the direction of “people-first” #2, until I realized that leaning too heavily in that direction might mean I wouldn’t be able to serve the community we built the product and the company for. My AI-approach incorporates more of #1 than I have in the past. I’m rebuilding my team after stepping in as a boomerang CEO, and every job description is now different, including my own.

But the one that resonates the most with me is #3 - play. At the most challenging times in my company’s journey - the wandering-in-the-dark phase in the beginning, the throwing-everything-out-because-it-was-a-pandemic-and-what-we-first-built-became-irrelevant-overnight phase in the middle, and the current-moment-in-time-as-I-reimagine-everything-yet-again phase*,* play has always been the light through the darkness.

Once again, play seems to be the word of the moment. Perhaps this resonates because my company is a social app founded on play. Or, perhaps, it’s because in the face of fear, the best antidote is play.

If you’re a founder reflecting on how to transform your business through this AI era, here are a few questions to reflect on:

1. What are your own values? What of those values do you already see reflected in your company?

2. What values do you want to embrace more of in your life? What values do you want to bring into your company?

3. What vision do you have for your company in 5 years, 10 years?

4. What role do you imagine having within your company on those timeframes?

5. How do you imagine AI will be part of your business in 2 years, 5 years, 10 years?

6. What commitment can you make today to the people who are currently working with you? What can you share about how AI will impact the company and their roles? What do you not feel ready to share?

7. How do you want to compassionately hear and be with the hesitations and fears of your team around AI?

8. How do you want to commit to helping people gain the skills they’ll need to continue to be part of your team over the next 5-10 years?

Want to chat about this?

As a founder coach, I work with series A and later companies who are answering the above questions. I offer twice monthly coaching sessions and leadership offsites that guide your team through AI transformation for systems, culture, product, & operations. Right now, I’m offering complimentary AI strategy calls to up to 3 post-PMF YC founders who reach out by 9/21/25. Reach out: lunarayemail@gmail.com.

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Most of the time I don’t have issues with productivity. Over six years as a founder and two years as a coach, I’ve dialed-in my own productivity system to keep me mostly on track. Quarterly goal planning for self and team, weekly task lists that I commit to completing 98+% of, time-blocking, and ample time for self-care and well-being throughout the week so I don’t have parts of myself fighting with other parts of myself most of the time.

But today, I was fighting. I still am. Man, when one part of you fights another part of you, you always lose. I see founders do this a lot when I coach them, and I do this too.

Since productivity isn’t usually an issue for me, when it is, I get really curious.

It’s like - oh, what have I not figured out yet? What have I not learned about myself? What is the part of me that’s not wanting to be productive on this thing that most of me seems to think I want to / should do trying to tell me?

Since the quarter just started, I set my goals last week. I set goals for both of my businesses - my YC startup and my coaching business. When I was only running one business, it was relatively easy to set goals. With two businesses, it’s an order of magnitude harder, since my time is finite and setting more ambitious goals with one business necessarily impacts the time and mental/emotional space I’ll have to achieve the goals I set with the other.

To the best of my ability, I’ve learned to set goals around the things that I can control vs the things I can’t control. I can’t control whether my startup will grow 10% MoM. I can control the actions I take to test hypothesis around what would make it do that. I can’t control how many potential coaching clients will reach out to me. I can control posting to Bookface with some regularity and trusting the right folks will find me at the right time when I can help them.

Beyond my quarterly goals, I have longer-term goals / intentions for each business. I’m building a $1M ARR coaching business and a $1B social & dating app (Plura). I have ideas around the time horizons for when I’ll get there, but those are loosely held. I have a decent amount of clarity around the actions I need to take to get there.

Productivity comes easiest for me when I know where I’m going and have broken down the problem into sufficiently manageable increments that my brain can understand the path ahead.

Hence, quarterly goals → weekly actions → daily tasks.

When you know where you’re going, it’s easier to step through the day-to-day, even the stuff that might not be as fun in the short term. But today, it felt hard.

Even looking at my to-do list today, it was mostly comprised of tasks I would usually find fun to do:

1. Write (here I am)

2. Post to Bookface and Substack (less fun, but easy / fast)

3. Meditate for 30 mins (having resistance there, 30 mins is too long)

4. Write a plan for understanding where Plura’s growth is coming from

5. Reach out to kick off hiring for a new data / growth role for Plura

6. Catch up on Plura emails & Slack

It’s not a terrible list. At some point, I was excited about each of these tasks (minus email, ugh). And yet so much resistance. I planned an entire birthday party for my partner this morning. I ordered new bathing suits on Amazon. I cooked lunch. I FAF’ed (fucked around forever).

And then I finally sat down to journal and figure out what is going on. Why am I in avoidance of these tasks that at other times would actually bring me joy to do?

Oh, because I don’t actually want the outcomes of those tasks. If I write well, I’ll get more clients. Do I want more clients? (I won’t post this until I’ve answered that question as “yes”.)

If I meditate, I’ll be calmer. Sometimes I like not being calm. It’s more exciting. Not calm is also the state my nervous system is most familiar with.

There is some big, ignored part of me that’s currently fighting with the rest of me around this whole future-of-my-company thing. While many parts of me, particularly what I consider the “self” (if you are familiar with parts work, this is the most “core” part of you that is present when there aren’t protectors in the way), believes in the future of Plura and believes there is at least a $1B business opportunity in our market (more likely closer to $2-3B), there is also some part of me that is not onboard.

And that “not onboard” part of me is waking me up in the middle of the night and driving my daytime procrastination. Until I finally listen to it and honor its wisdom and its message, it’s going to keep doing the same things. It might even switch to more severe tactics.

The truth is, I’m not totally sure I know what that part is yet, or what it wants for me. I know it wants to keep me safe. I know it has kept me safe.

It feels like there is something at the intersection of not wanting to go back “there”* and fear that even it if I did and it were to be different this time, “success” would bring with it a whole host of other problems that I don’t currently have today.

*To me, going back “there” represents the place I was when I was running my company full-time as a solo founder, where the intensity of it took an extreme toll on my physical health, rendering me in debilitating chronic pain and disabled. Obviously there’s a wisdom in the warning signs my body is giving off of not wanting to go back to that place. And this time, there’s a very real potential cost: cancer.

We play a high stakes game of poker as founders, don’t we? 😂

When we gamble with our health and with our lives, there’s really nothing greater. We only get one.

And then there’s also the fear(s) of what success would bring with it. Disconnection from my own community if I were to become wealthier than I am now. Not knowing what to do with myself if I had endless financial freedom. A public identity that I have limited control over. Death threats from people who don’t understand why we do what we do (we serve queer, trans, and non-monogamous communities). Oh, and more stress 😂.

When I work with founders as a coach, I often witness how activation feeds more activation. Fear begets more fear as you start to fear the fear itself. Anxiety begets more anxiety as you become anxious about the anxiety. Stress begets more stress as you become stressed about the stress.

In my case, I know that my fear of the stress - because of the fact that it landed me disabled last time, and possibly caused the pre-cancer - is begetting more stress. So the moment stress emerges, I loop on it, fueling it’s potency, and want to run away.

This is just how nervous systems work. We’re evolutionarily wired to save ourself from predators, and our nervous systems that evolved thousands of years ago respond the same way to the stress impulse from metric dropping as they do from a tiger chasing us. As long as there’s some part of our brain that fears the worst, it can take us a little while to come back into regulation.

The way we do it is by existing in the world around us and noticing signs of safety. Noticing birds singing (they don’t sing when there’s a predator around), noticing the objects in the room (we are physically here, not actually needing to run from a predator), deep breaths with a slow exhale, or co-regulating with another person who we trust who is calm (co-founders are great here, and when that fails, there’s always coaches 😉). When we notice signs of safety, we can calm down, knowing it will all be ok.

And on some time horizon, it will be.

Plura is profitable, so we have a decent amount of breathing room. I’ve built a successful coaching business faster than just about anyone else I’ve known, so I’m confident I’ll continue to do that.

Cancer is this interesting wildcard on top of everything else.

Despite having more confidence in the future of my businesses than I’ve ever had, there is a fear that’s present too. If I had to trace it to it’s source (I’m trying here, ok), it’s this real fear that I get to pick two of the three: a billion dollar Plura, a very successful coaching practice, and / or healing from cancer.

And when I set my goals, I implicitly picked the first two. Because I didn’t set any quarterly goals around my health.

And frankly, so far this quarter, had I set goals around my health and the daily practices I know honor my health, I’d have missed most of those goals.

I’m only one week in, and I’ve met my Plura and coaching goals, and failed at my health goals. Womp womp.

Ok, I think I’ve found the part of me that needed to be heard. It’s the part buried deep in my uterus, that may or may not be there (Schrodinger’s cancer, anyone?), that’s reminding me there is no point in building a million dollar coaching practice or a billion dollar software business if there’s no life to enjoy them.

And just when I thought I couldn’t possibly work less and still run two businesses, here I am, contemplating how on earth I am going to do exactly those things.

I recognize my current stress-loop, insomnia, and procrastination combo as just another neuroplastic symptom. Since I’ve backed myself off the cliff of neuroplastic chronic pain through a mindfulness and meditation practice before, I actually know how to do this again. I just have to choose to.

Update: one month later

I’ve created more space in my week for my health, and I’m no longer fighting myself in a procrastination loop each Monday. I also took a week off, which gave me a fresh perspective on my approach to “pushing” each business forward. I have a lot more peace and a lot less procrastination now.

I time-delayed this post until I felt ready to take on a new client in my coaching practice. I work with post-PMF founders who have a clear vision of the future they are creating and want support to get there. If you’d like to hop on a discovery call to see if we’re a fit, reach out: lunarayemail@gmail.com.

In case you are also a female founder (or know of a female founder thinking about this), I’ll just share a few facts that helped me gain comfort with my decision to have my company pay for my own egg freezing:

1. Companies pay for egg freezing all the time. Meta, Google, Mercury, etc.

2. Companies pay for founders/executives to “save time” - executive assistants, etc.

3. Investors invest in the founder’s ability to run the company. If the founder’s preference is to delay childbearing to focus on the company, that is also aligned with the investor’s interest.

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And lastly, if it’s helpful for another founder to give you permission to do this or say it’s normal, well, here I am saying those things.

Here’s my story.

When I was at Meta (Facebook at the time), I had an incredible fertility benefit. They would cover the costs of my egg freezing. I was 27 when I asked my doctor if I should use the benefit. My very well-meaning doctor pointed out that I was already married and had the man I’d want to have kids with, and since I thought I wanted to have kids around age 32, I didn’t need to freeze my eggs. I listened to that bad advice.

I always knew I wanted to start a company. As I approached 30, I thought about my timeline for doing so with also having a family, and realized I needed to get going. At 29.5, I quit my job and applied to YC.

When age 32 came around - the age I thought I’d start trying to have kids - I was a solo founder running my first seed-stage startup and it was the middle of the pandemic. I was not ready to have kids.

I wrestled quite a bit with whether to have my company pay for embryo freezing for me. As a founder, I paid myself 1/3 of what I made when I had left Meta, and while it covered expenses, I wasn’t exactly rolling in a spare $17k (the cost of embryo freezing). I could have dipped into savings, but that seemed stressful, and yet another sacrifice for my startup.

I could have paid myself more temporarily to cover this, but that wasn’t efficient from a tax standpoint. It actually just made the most sense to make it an executive benefit and expense it.

But the important thing is: you can have your company pay for your fertility preservation. If you are the CEO, it’s your choice.

There’s so many complex emotions with the decision of whether to have (and carry) children in the context of being a female founder - being a founder is hard enough, bearing, birthing, and caring for a baby on top of that can feel totally overwhelming. I have the most tremendous amount of respect for the female founders I know who have done that. If you’re a man reading this post with a female co-founder, know that this could be something she’s thinking about, and the best thing you could do is support whatever decision she makes.

I was living life yesterday. It was the day we closed on our new home for our new life in San Diego, and the day my partner earned tenure after his nine year journey to becoming a law professor. These are milestones that were so many years in the making. So much to celebrate.

As we were about to head out the door to our celebratory take-out dinner in our new home, I got a call from my doctor.

She was as surprised as I was to learn the test results of a minimally invasive removal of a uterine polyp as I prepare for pregnancy: despite having absolutely none of the underlying risk factors, my results indicate a endometrial pre-cancer.

As I sat on my new deck in the new home we had bought for the new family we hoped to create, I explained to my parents (who can’t wait to become grandparents) what this likely means for my family planning: delays of at least a year while we attempt to treat the pre-cancerous symptoms, and eventual removal of my uterus and reproductive system to prevent cancer altogether - or find and remove it if it’s already there.

Life has been coming at us in avalanches lately, with each subsequent avalanche so much larger than the previous that it makes us laugh at the stress we had from the one that came before.

In recent posts I shared how I became a boomerang CEO, unexpectedly stepping back into leadership of my YC company after two years away while running a full-time founder coaching business. Last week I launched my coaching work publicly for the first time. Next week, I’m moving into and setting up my new home.

And now, this.

In a cosmic reminder that we don’t get to control everything in our lives, it started to become clear why I built a meditation practice two years ago. My meditation practice is part of my spiritual practice, one that incorporates indigenous medicine tradition (ayahuasca and others) in shorter “burst” treatments with an ongoing “maintenance” protocol of daily meditation. As life has kicked up its velocity, I’ve found it harder to sit my butt on the meditation cushion and actually meditate - to-do lists flood right in, next steps on each of the major life items trickle in in my attempt to control a chaos that’s become unbounded - and then I remember to go back to “meditating” (whatever that means).

But I built the practice towards the end of my founder journey (part 1), when I really didn’t know what it meant to meditate or why anyone did, but grandmother ayahuasca told me to, and I like to respect my elders (yes, a plant spirit). And what I’ve found was a simple way to downregulate my nervous system, even if just by 2%.

As founders we live in incredible states of activation, cortisol flooding our bodies 24/7. I’ve seen this in almost every founder I’ve coached. It isn’t a chill life (for most of us). Over time, this takes its toll - on our bodies, our health, our companies, our loved ones. When we’re in states of activation (stress - even if we don’t feel “stressed”), we’re more reactive to stimuli (e.g., anything going wrong with the company) and we’re shorter with our loved ones. It can be harder to access states of joy without an equally intense experience to kick us into presence with fun (e.g., a raging late night bender), whereas before a simple dinner party with friends was enough to bring us into presence and relaxation.

My meditation instructor Dustin DiPerna likes to remind us that meditation is a choice. Even when we are “meditating” - sitting in a meditation posture and going through the steps - we have a choice whether to really commit to it or not. I have spent many hours of my life on the meditation cushion crafting to-do lists for the day ahead. While they may give me some illusion of control, to-do lists don’t actually downregulate the nervous system. Meditation does. I know that committing to meditate will be an important part of the path ahead.

One of the other lessons I’ve learned from my spiritual practice is radical acceptance of what is. Fighting it and resisting it is what causes the strife. As I start this next chapter - another health journey, running two simultaneous companies, and moving my life to a new city, I’m learning to tune into radical acceptance. The cosmic joke of the moment is I don’t seem to have a choice but to radically accept.

I don’t know in this moment how I’ll be able to navigate a health journey with all the appointments and treatments in front of me while running two companies. I’m deeply committed to the founders I serve as a coach. The social app I built, Plura, is an incredible community I am deeply dedicated to serving. I know that on the other side of this will be profound lessons that will benefit those who I serve. I don’t know what they are yet, and I’m beginning to radically accept the not knowing.

But if there is one thing I’ve learned in the last two years, it is that I need to serve myself first. Put on your own oxygen mask before helping others. So tomorrow, instead of skipping the lab work I’ve been trying to get done for a year, I’ll be heading to the clinic for tests, and everything else will happen after.

Power is often projected onto the person in power by the person with less power. Unless the person in power has done their own work to become aware of that power, this can easily happen unknowingly to them. Hence, in the classic example of white men having social power and privilege in society, many white men are simply unaware because the relative difficulty faced by everyone else as a result of having less social power and privilege simply goes unnoticed by many white men. (This is not an attempt at a gender attack, it’s merely summarizing an example of what’s been discussed ad nauseam elsewhere.)

In the context of VC / founder dynamics, typically VCs have more power. VCs get to decide which businesses get funded or not, and founders are at the mercy of those decisions. In some instances when a company is doing exceptionally well, is already profitable and growing quickly, and/or the market dynamics shift heavily in favor of founders, the power balances more evenly or even tips in favor of founders, and founders are more likely to get to call the shots on price, etc. Oversubscribed rounds shift power towards founders.

It’s not a secret that around 2% of VC funding goes towards women founders. In a sad way, this makes sense: seed stage funding, especially pre-PMF, is largely based on “vibes.” VCs are pattern matching based on who they’ve seen succeed before, and since fewer women founders were funded before, there’s simply fewer examples of successful women founders to pattern match to. (You can drop in most underrepresented identities in tech for roughly the same story.)

Layer onto this the fact that there’s historically been a strong investor bias towards at least one founder being an engineer (for good reason), and the fact that women make up a smaller fraction of software engineers, and we have the landscape of gender in tech that we have today.

And that’s all about to change.

In my second business, as an executive coach for founders, I see where this is all going.

As more and more products hit the market based on vibe-coding alone, pre-existing technical skills within the founding team become relatively less important to finding product market fit. In their place, empathy for customers, the ability to talk to users to tease out feedback and unmet needs, and knowing how to tailor the product towards those become more important.

Founders with technical skills are still needed for building and scaling robust technical systems, but over time a smaller fraction of tech startups will require excellent technical skills within the founding team. If founders can get to product market fit and revenue traction on vibe coding alone, they can hire to unblock technical issues as the product scales.

Essentially the balance shifts from engineering excellence as as core competency of a founding team towards an even greater emphasis on empathy and the ability to build trusted relationships with customers - skills that women have long excelled at due to our socialization.

Layer on top of that the ability to hyperscale with lower costs - AI agents for customer support, operations functions, etc. - and access to capital becomes less important. The VCs won’t hold all the power for determining the winners and losers at the early stage because capital requirements will be much lower. The relative disadvantage women have always had in a funding system built to pattern match towards men will shrink.

I see a future of tech where it’s easier for people to start companies who don’t have power and access today.

As technical and funding barriers shrink and the importance of empathy rises, we’ll not only see more business successfully started and run by women and other underrepresented identities in tech, but we’ll also see more businesses solving problems uniquely faced by communities that aren’t being served today. And that’s a future of tech that I’m excited about.

One of my specializations within founder coaching is working with founders who want to create excellent places for diverse teams to work. If this speaks to you, feel free to reach out for a discovery call. Lunarayemail@gmail.com.

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In my last post, I wrote about my intentions to maintain the balance I’ve found in my life running my own founder coaching business. I pledged all the things I’d do differently, with the perspective of a two-year break from being a founder, the lessons learned from a spiritual journey that took me to the edge of the planet and back, and the observations from coaching over 40 other founders.

But taking over the reigns on a bucking startup is hard. It reminded me how much of what we do as founders is hard. Even though I now know what my sustainable work hours look like, the sheer overwhelm of trying to get a handle on things drove me to compensate for chaos by adding in more hours. I know it can’t work that way long-term.

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Even though I know what to do - where to focus my time, how to spend my energy, and what capacity I realistically have to work on this business - I didn’t do it starting day 1. I’m telling myself some sort of story that I’ll get to the work-life balance thing once I get a handle on what’s going on right now. There are urgent things I am days behind on with the unexpected transition, and the story I chose to believe is that I have to do all those things yesterday. (I couldn’t do them yesterday because yesterday I was in the operating room - and yet the world did not fall apart.) My story is sustainability will come after I do those things.

And yet the way we live our lives today is the way we live our lives.

The way we intend to live our lives tomorrow is not the way we are currently living our lives.

Almost all of the founders I’ve coached have faced some form of this narrative: I’ll do XYZ (which is the most important thing for me to do) when I get enough time, after this next milestone happens, once I hire this key employee, after Saint Patrick’s day… The reasons are infinite. But once again, the way we live our lives today is the way we live our lives.

If we (founders) aren’t prioritizing the most important thing with the greatest importance, then we’re prioritizing the wrong thing. And that’s hard because there’s always a million urgent but less important things.

What happens to our companies when we do this? We send the message to our teams that the most important thing is not, in fact, the most important, otherwise we’d be spending our time there. And our employees learn from our example that it doesn’t matter if they are working on the most important thing. When we prioritize what’s urgent over what’s important, we tell our employees (whether directly or subconsciously) to do the same.

And then what happens to our business? We sprint hard all the time to accomplish a million micro-tasks but no one is steering the ship with intention.

Why do we do this? As I’ve gotten into the nuance of this with founders I’ve coached, this is a recurrent theme. There’s a dopamine reward system that hits every time we accomplish a small task - unblock an employee by responding to a Slack message, check off a minor item on our to-do list, etc. It feels like progress to do many micro-tasks in a day, even if that means we delay the more important ones indefinitely. The work that seems to get punted is the high-level strategy, the planning for what we’ll do this quarter, the team changes that need to be made, the bigger product pivots, etc. I’m guilty here too.

The way out of this is to choose to do it differently and to hold yourself accountable. As a coach, this is perhaps the greatest gift I give to founders. I’m simply the person who asks you each session what the most important thing is for your business and helps you get that done.

Whether that’s blocking time on your calendar, pairing with a teammate, exploring the fears that are blocking you, or simply holding you accountable to the goals you state out loud each session, we find the thing that works for you and we do that.

And now I have to find the thing that works for me…

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I remained Chair of the Board of Plura and was still involved, but in a much lighter way than I had been before.

It became clear to me a few weeks ago that I needed to come back. After almost two years away, the company needed a shift in direction to take it onto its next chapter, and that is one that only I can make. I never thought I would be the CEO again (and, for now, I refuse to claim that title).

So now I’m in this interesting position, asking myself the question: if I could do it all over with the lessons of the first four years running it and the last two years healing from it, what would I do differently?

The company hasn’t changed that much. We’re on the cusp of profitable (phew). We’ve tried so. many. things. And when they didn’t work the first time, we tried them again. We know what works in our business and what doesn’t work.

The thing that’s changed is, well, me. After I left my day job as CEO, I spent 6 months healing my body, mind, and spirit, meditating, walking in nature, and listening to silence. About 8 months in, due to Pain Reprocessing Therapy, and frankly, not running a company, my chronic pain healed. I then started coaching founders. I trained in four somatic coaching modalities to better understand the link between mindfulness, stress, healing, emotions, pain, and productivity. I took a short break from coaching to run an extensive acquisition process (that was fun!), and in that time, learned a lot about our competitors. I’ve coached over 40 founders and learned about how they run their companies and the challenges they face, and what works for them to overcome them. It’s been a symbiotic relationship: as I coach them, I learn about what works for more people, which then makes me a better coach, and will make me a better leader of my company.

And once again, I’m being called to lead.

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There are things I know I’ll do differently this time. For starters, my boundaries will be different. I always thought I should be working more hours and always carried a lot of guilt when I wasn’t doing that. I just won’t think that way anymore. I have a thriving full-time coaching business that I love, and I won’t be giving that up. So I’ll be running my company in 1-2 days a week. Will that work? I can’t wait to find out.

I love having mornings to run on the beach or in nature, do Pilates, meditate, and spend time with my family and my dog. I like starting work at 11 and ending at 5 or 6. I’m going to keep doing that.

I like having weekends and evenings to spend time with the people I love. I know I’ll never get this time back. My parents are aging but still vibrant. My friends are wonderful and fun to spend time with. My niece and nephew are 3 and 6, and they won’t be those ages for long. My grandma is 100. I want to spend time with all of these people.

I delayed starting a family because I was running my company. I won’t do that any longer.

The great irony in all of this is I started this company because I was lonely. Plura was an answer to a pandemic-era problem I had: wanting to connect with people when it was impossible to do so. In the four years that followed, I lost sight of what mattered most: my own people, my own community.

And, like a classic hero’s journey, I went on the most epic adventure of my lifetime just to come back to right where I began. In the final step of the hero’s journey, the hero “returns to their ordinary world, undergoes a final test or transformation, and shares the knowledge or treasure they gained.” I’m not sure what my final test will be, though I’ve got some ideas. If you want to hear about the knowledge or treasure I gain, follow along here.

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