On how timing always seems to be shit in startups, as in fatherhood

But also on how you can't let that stop you

Welcome Entrepreneurs!

I’m writing to you from a house full of kids. A child at our oldest son’s montessori contracted COVID, so both our boys are at home for a week while Laura and I tag in and out between our work and art projects with the boys.

Early in quarantine, the same situation felt like a nightmare, but this time it’s actually been kind of great. There’s still the emotional pull toward work when I’m with the boys and that toward being a dad while I’m working — the very tension that made early quarantine so miserable — but I’ve learned to let that tension simply be there, and have improved at intentionally returning to where I am at any given moment.

Which, right now, is writing to you.

I’m glad you’re here. Let’s dive in.

"This is the real secret of life -- to be completely engaged with what you are doing in the here and now. And instead of calling it work, realize it is play." — Alan W. Watts

On how timing always seems to be shit in startups, as in fatherhood (but also on how you can’t let that stop you)

A profound image about fatherhood, laying out the entire journey in nine simple, frighteningly brief steps, found its way to me through the miracle of the Internet.  And thanks to this profound image I was reminded to turn my phone off and build a pair of secret agent shoes with my four year old son (complete with string-attached glue sticks to adhere the feet of any following bad-guys to the floor).

I remember in the early days of building VNN, when Laura and I used to talk about having kids.  The topic first came up around 2013, when the first of our friends had theirs.  It seemed like fun.  We both knew we wanted to have kids (three, we agreed), but every time we talked about it we would inevitably end the conversation talking about timing.  Whether this was the right timing, or we needed to wait until timing was better.  Throughout that period I was traveling to the coasts weekly (sometimes 2x), so it was a legitimate concern.  I couldn’t imagine being a father, but I also couldn’t imagine not being one, at least at some point. 

So timing was the refrain, for a long time.  A refrain I’ve heard from more pre-kid entrepreneurs than I think any other.  

And then one day in 2015 Laura and I went golfing.  For us, this meant and still means about 4 holes of golfing together, followed by 5-14 holes of Laura driving around watching me golf and enjoying the sun.  We went golfing one day, and the topic of kids came up as it had on so many other occasions.  Except on that day, something was different.  

Even as I look back I couldn’t tell you what it was.  Maybe something in the air.  Maybe I was playing well.  Maybe having raised a round of financing a month prior I was feeling a bit untouchable.  I can’t say.  But whatever it was, on that day when the topic of timing came up, the discussion didn’t stop.  

We considered timing, as always.  I was still traveling all the time, Laura was running her company Blackbird, and timing was still as shit as it had always been.  We considered all this, but we also considered the years that had passed since we had first discussed kids, and that, as far as we looked into the distance, timing still looked to be shit.  

For the first time, that day as we were carting through the sunshine, the crazy hecticness of our lives didn’t look like an anomaly that would be over at some point.  A matter of timing.  It looked like, simply, life.  The life we had chosen looked like one that didn’t support kids, but it was never a matter of if, for us.  It was always when.

And for the first time that day, we figured that now was as good a time as any.  

In the months leading up to his birth, as we did our showers and put everything we could think of into place, amidst all the excitement I remember a bit of panic set in.  I was back in fundraising mode, flying all around the country to raise our Series B, and after a month of hotels I still didn’t have a lead investor. Prospects, sure, but put prospects in one hand and shit in the other.  See which one’s worth more.  

What was going through my head at that point was timing.  Now was a terrible time to have kids, I knew.  How in the hell was I going to keep our company growing, keep our people employed, while still changing diapers?  Timing was awful, it was clear.  But it didn’t matter because he was coming.  

Kaspor Jordan Vaughn was born in 2016.  Kaspor, for his great grandmother, and Jordan, because I’d never made it to the NBA.  

I stopped negotiating legal docs for our Series A-1 round for about a week after the birth, and called it paternity leave.  The first three months after that were hell.  Sleepless nights, screaming and pooping.  The stuff you hear about when you hear your parent friends talk about kids, just way, way more of it.  All the time.  During those first three months I remember wondering if we’d made the right decision.  There was just too much to do, and too many people counting on me.  We closed our financing round, but I still couldn’t manage, I knew, and I was going to let down my team and my investors.  My company would fail by the time Kaspor was one, maybe two, and my soul would be sucked dry by a corporate gig a year after.  When asked about this time in my life, I’ve been known to say “the first 90 days were like Vietnam.”  I’ve never been to Vietnam, but I imagine people were just trying not to die over there, and that’s what it felt like. 

But then, less than 30 days later that phase was over.  Laura was back to work, we’d developed a routine, and I realized (after a meeting in which a manager-who’d-joined-the-company-as-a-college-intern informed me about a critical fire, and also that she had handled it and was just letting me know) that our company was succeeding without me working 80 hour weeks.  I was traveling less, home by 5:30pm every day, and not only were those things not a problem, our company was growing faster than it had in years. Out of necessity I’d given my team space, and in that space they’d developed a habit of stepping up to tackle things they never had before (culture played a big role, which I’ve written about here).

Somehow, my son Kaspor had Miagi’d me into becoming a good leader.  I realized this parked outside our house at 4pm, the sun shining and Kaspor sleeping in the backseat.  Timing had never not been shit, but somehow through it all things had found their way.  Two years later I sat in the same spot on the side of the road, reflecting that the first 90-days with our second son, Leo, weren’t even so hard.  Paternity leave had been a full month for Leo, and it didn’t surprise me when that was one of our top sales months ever.  Business continued to grow despite my leaving the office at 5:30 each day, and while part of me stressed out over every latest thing, another part of me, a growing part, was considering taking a couple month sabbatical.  Timing was shit, as we were raising capital again, but that didn’t scare me like it used to. 


There’s a lot of things you think as a first time parent, that end up not being true.  One of those things you think, particularly with your first infant, is that whatever things are like, whatever kind of shitty existence you’re putting up with to keep your child alive, that that’s just your life now.  That you’ve made this decision, and now your life is just shit and no sleep forever.  Such is the burden of the firstborn, that they have to deal with our manic-depressive whiplashing while we figure out what the hell we’re supposed to do as parents.  Not that different from what my first startup would have felt, had it been conscious (that first startup would have had some serious complexes had it grown into an adult).

But amidst the chaotic craziness of having kids, like that of building companies, part of what my expanding bald-spot has taught me is that nothing is forever.  Even the deepest jungles are really only about a block wide, and if you just keep walking you’ll see daylight before you expect.  And then you’ll look back and wish you’d taken pictures of the foliage while you were there.  As I build my fourth company, as Kaspor is learning to ski and Leo is saying “no” to literally everything we say, what’s clear to me now is that even as irritating as an obstinate toddler and a company with virtually no leverage to speak of can be, they’ll be gone soon enough, replaced by the next version of themselves.  

And I can’t turn around, so I’d better take some pictures.

Of course I still forget, sometimes, and find myself on my phone while my kids strategize how to detain would-be antagonists to their secret-agent agendas.  And for those times, I’m grateful for the random guy posting the random picture to his random Twitter account that changed my afternoon and maybe my life.  Despite its flaws, on days like today I’m grateful for the miracles of the Internet.

Miracles like this picture, which is now also my desktop background:

Now I’m going to go figure out how to make wings for a Matchbox car.

(HT: Anushri Kumar and Compound for editing)


Who is Ryan Vaughn?

I’m an executive coach for startup founders, a role in which I get to help founders expand into leaders. I’m a 3x Founder/CEO who’s raised $20m+ in VC and built a market-changing company, as well as two other companies that taught me things. I’m an avid writer, meditator, reader, athlete, father, husband, amateur physicist, student of leadership, and adventurer. I’m also none of those things. But I am glad that you’re here. Here’s a more detailed bio.


One: In and Of Itself (Hulu)

I’ve never given a movie recommendation before, but I have to lead with one this week. If you haven’t experienced In And Of Itself, a one-man-show about identity by Derek Delgadio, do yourself a favor and do so tonight. I also suggest you optimize the experience by not reading anything about the movie and going in completely blind, but understand that that takes a bit of trust. If we don’t yet know each other like that, feel free to click the link below to learn more.


Two: Revamping our cultural operating system (Medium)

Michael Katz, CEO of mParticle, described a situation with which I am very familiar in this Medium post. He walks through how he identified that corporate culture was becoming an issue (while still growing 100%+/YoY), how he connected the symptoms he was seeing (employee engagement, etc) to the cause that his corporate operating system was obsolete (“we were attempting to grow up but still behaving like teenagers”), and how he implemented a solution that added psychological safety without sacrificing results. Loved this.


Three: Doing vs Being: Practical lessons on building an agile culture (McKinsey)

Four interesting and true parables about how companies are responding to the increased entropy in their business (and society) by building agile cultures. Part of me feels like this is behind the times as I find myself spending most of my time building lean leaders leading agile cultures, but then again the majority of companies still ignore the warm & fuzzies entirely so McKinsey talking about it may help.


Four: A healthy economy should be designed to thrive, not grow

“Hey doc, I’ve got a growth here.”

There is no scenario in which perpetual growth of a thing is good for the system in which that thing lives. And yet the one thing both political parties can seem to agree on is that our economy must continue to grow at all costs. Many of us are so submerged in the growth Kool-Aid that we may have never questioned it. This Ted talk by Kate Raworth lays out a very rational alternative named after delightful pastries. If the talk makes sense to you, the link below it can help you get started.


Five: VC funds at / below $200M in size (new funds raised since 2011)

If you’re raising money for your company, here’s a (semi)secret list of funds who have raised new capital since 2011 (meaning they likely have funds to invest). Yet another miracle of the Internet.


I hope this week’s essay resonated, especially if you have kids or a startup. Being a father and a CEO are two incredibly important roles that can seem mutually exclusive at times, God knows they have to me, but in hindsight they always seem to fit just right.

Whatever you’re juggling, be well. And thanks for reading.


PS> Did someone forward this to you? Join our fast growing community of Purpose Driven Entrepreneurs by subscribing below.


Top Posts

If you liked this, check out this list of my top posts, read and shared by thousands of entrepreneurs.

Here are a few of my favorites: 

Executive Coaching for Entrepreneurs

There’s a reason every elite athlete in the world works with a coach. You need more than one perspective to see your best work.

I’m privileged to work with amazing humans every day to help them grow into extraordinary leaders, and support them in building the company of their dreams. As a 3x founder and CEO for 15 years myself, I coach entrepreneurs how I want to be coached — laser focused on results, without the fluff.

To find out more, click here or simply reply to this email.