I Can't Breathe

[Originally posted on Medium]

I've struggled with whether or not to write this. My stories aren't all that special. There are countless others who've experienced worse.

But I'm writing this to those of you in my life that don't quite understand what's going on right now. Who think that people are making too big a deal out of all this.

I wanted to blame you for not getting it, but maybe in some part, it's my fault.

It's my fault that I haven't told you my stories. It's rare that I've opened up about my pain. And because of this it's possible that I've left the impression that I haven't been affected. Maybe I'm the example that you go to when you make the argument about how everything's okay.

I haven't told you that I can't breathe.

I didn't tell you about the first time I realized that my life in America was going to be different because I'm black. When I took one of my best friends to a middle school dance. And then her mom found out after the fact, and forbade the girl from speaking with me ever again. Because she's white, and I'm black.

I didn't tell you about how that broke my heart, and birthed a rage inside of me. I didn't tell you that her mom was an employee at our school, and I had to walk by her every day, feeling her eyes burn into my back.

There's a story I was sold: keep your head down, work hard, get good grades, stay out of trouble. If you do all that, your blackness won't matter.

I didn't tell you how suffocating that was — to be held up to that standard, just in the hope that I get seen in the same way as the people around me.

I didn't tell you about all the moments in my life that helped me understand that this story was a lie. The comments heard in earshot. The furrowed brows directed my way. The jokes I didn't find funny. Wondering about the job offers I didn't get. Wondering about the investors that told me no.

How every time I started to forget the story was a lie, someone would faithfully remind me.

I didn't tell you about the time I took a road trip with friends when I was 15 years old. When we started playing with a BB gun in the car, and someone called the cops. I didn't tell you about the shotgun pointed at my back, my hands in the air. How I knew we weren't speeding, so was confused about why we were pulled over.

I didn't tell you how I couldn't understand anything he was saying because the wind was loud and there were cars whizzing by us. How he started screaming because clearly I was doing something wrong, but I didn't know what. And how all I could think about was the shotgun blast that could rip through my chest.

I didn't tell you how I felt after John Crawford. Or Tamir Rice. I didn't tell you about my tears.

I don't tell you about all the ways I live my life differently than you do. How I think about it nearly every day, and it's suffocating.

How it comes up in things you might not expect, like when I trained for a half marathon. How I never ran after dark. How I chose clothes to try to make it clear to everyone that I was just a runner, not a black man running away from something. How I'd sometimes cross the street if I was coming up on someone too fast.

I didn't tell you how I felt after Ahmaud Arbery.

I don't tell you how it's not just those with hate in their hearts that I've come to fear. That I fear more the system that might not protect me.

So I'm telling you now. I'm one of the lucky ones. But even still, I can't breathe.


I almost shut down Formstack.

In January 2006, I quit my job a couple weeks before our first child was born. My wife had also quit her job to take care of our child full-time. We had some savings built up, but it was only going to last a few months without any outside income.

I launched Formstack at the end of February after a month of nonstop work. I was proud of the one-of-a-kind product I'd built, certain that it’d take off and be a runaway success.

Shortly after launching I learned of a similar product that’d been on the market for a few months. And then two others that launched within a couple weeks of me. I was gutted.

I had my first paying customer not long after launching, but by the end of March I was only making $75.

In April I made $72.50. Churn sucks.

As my personal expenses grew (diapers aren't cheap), I scraped together consulting income to pay the bills. And as I found more clients, it became harder and harder to devote time to work on Formstack. I could bill $100/hour for consulting work, so why would I spend that time working on a new Formstack feature with no guarantee of future payback?

By the end of the year Formstack had grown, but was only making about $1k/month. I was getting burnt out, money was tight, and the numbers weren't working. It made sense for me to shut it down to focus on consulting. I struggled with the decision for several weeks, and came close to pulling the plug.

I can’t remember exactly why I stuck with it. I know I still believed in the vision and was proud of the product. And I didn’t love consulting. It was a means toward an end — my dream to build a product company. But maybe more than anything, my stubbornness was why I didn't shut it down.

Whatever the reason, I’m glad I didn’t give up.

With a lot of hard work, it grew 10x in 2007. And six months later I was able to stop consulting and focus on the business full-time.

Fast forward a decade, and Formstack will end this year with over 25,000 paying customers, 200 employees, and tens of millions of dollars of revenue.

Success wasn't a straight line. There have been countless hurdles and potholes along this journey. And many more to come.

But I’ve never been luckier to be so stubborn.

Don't Outsource Your MVP

If you're starting a tech startup, please don't outsource the development of your MVP to a third party. Find a technical cofounder.

I know I’m not telling you anything you haven’t heard before. But please listen. I've heard too many heartbreaking stories from founders that tried to do it the hard way.

The founders that funneled tens or hundreds of thousands of their own money to a dev shop, without a product that works. Bled dry, a few thousand at a time, hoping that this time, they'll fix all the bugs and ship critical features.

The founders that gave up almost half the equity in their company to launch an MVP. Only leads aren't converting, and maybe they'll find traction if they add another feature or two. But the project's "done", so founders can't get any more time from the dev shop. And new investors won't fund the company because the cap table's all screwed up.

A Confession

Many years ago, I started a custom dev shop. Pretty quickly, my entire client list consisted of nontechnical founders who were using me to develop their MVP.

I loved startups, so was eager to work on these types of projects. And I was pretty picky about which ones I took on, so only worked on products I believed in. I hit almost all my deadlines, and charged way less than most of the competition.

But a couple years in, I shut down the dev shop to work on Formstack full-time. I transitioned all my clients to other firms or freelancers, and applauded them from afar.

My first startup client brought all development in house shortly after they launched. They raised a few $M from angels and VCs and later exited to a Fortune 100 company.

My other clients met less desirable fates. None of them got much traction with their MVP. I don't remember any raising that much money from outside investors, if at all. Some had enough capital to fund a few more iterations of development to give the company a shot. All those businesses are now long dead.

I've felt guilty about this. I put a lot of heart and sweat into the work I did for them. We built a good relationship while working together, and I wanted to see them succeed. How was I able to make Formstack successful, and not do the same for them? How much of the blame for the failure was mine?

But as I reflected and listened to other founder stories, I realized launching with outsourced development is a near-insurmountable uphill battle. There wasn't anything I could've done differently for my clients. The odds were stacked against us.

You'll Move Too Slowly

It's critical, as an early stage startup, for you to be able to iterate quickly. I don't care how perfect your idea is — you'll need to make frequent changes in response to your product touching real-world customers. You'll more likely be struck by lightning than not have to make changes to your MVP to find traction.

The dev shop's going to be working on many projects in parallel. So your 40-odd hours of resources will be spread across several weeks, not one. Or, they're going to assign resources serially — once your project is "done", they're on to the next one. And good luck getting resources until that one's complete.

Nothing beats working with a cofounder or team member side-by-side, in real time. Critical bug that's preventing new users from signing up? Fix it now. Metrics looking bad and you need to overhaul the onboarding process? Drop everything else and crank away to ship by the end of the week.

Some dev shops will be able to respond quickly, but only for a while. Their business model is always working against you here. For every change, you'll need to go through the process of scoping out requirements, bidding, and scheduling out resources. And as a founder with time working against you, that'll bring lots of stress and frustration.

You'll Burn Too Quickly

If time isn't against you, cash is. Working with a dev shop will always be far more expensive than working with a technical cofounder or team member who's doing the work.

Again, there's no getting around it — there's overhead baked into the business model of the dev shop. They need to make money. For every $10k you pay them, I guarantee that you can find a great full-stack engineer who's eager to work on something with you for a fraction of that price.

And what most first-time non-technical cofounders don't realize is how much work comes after the launch of the MVP. The dev shop may even say that to you, but it's easy to let optimism cloud your judgement. You'll spend a tiny percentage of your total development costs on the MVP. Where it gets really expensive is afterward, when all those bug fixes and iterations start adding up.

You might get into this trap where you blow through your bankroll before you're able to demonstrate traction. Or even if you've already raised some investor money, you might funnel all that to the dev shop before hitting important milestones. In either case, it's practically impossible to get the next round of funding.

In the end, this ends up costing far more equity in the long run. It's cheaper to find a great technical cofounder and give them 20-50% of the company on a vesting schedule.

You Won't Build The Right Thing

The result of all this is that you likely won't get a chance to build exactly what you need to put your startup on the path to success.

It's not only the lack of speed and limits of cash that lead to this. It's the intangible of working with a cofounder that's bought into the startup as much as you are. Someone whose hopes and dreams hinge on making this work. Whose anxieties and fears revolve on making sure this thing doesn't fail. Someone that's thinking about your startup in the shower, on the drive home — just like you are.

You're not going to get this from a front line coder at a dev shop, no matter how skilled they are.

Who's going to put in the effort to find effective ways to cut development time? Who's going to search endlessly for elusive opportunities for 100x outcomes?

Some Exceptions

There's no one way to build a successful startup, and exceptions to every rule. I'll even bend my "have a technical cofounder" rule for a few exceptions.

Is your startup not really a tech startup? If custom software isn't really core to your business, then none of this applies. If you're creating a shoe company, work with people that can help you build the best shoe possible, whether or not they can code.

Do you already have a lot of your own money that you're willing to spend to get this startup off the ground? And you're unusually averse to the idea of hiring a half dozen engineers with that money instead? Then go forth and bless a local dev shop with your riches.

Do you have experience launching a successful product within another company? And done so as an engineer or product manager? And you're only planning to hire a contractor or two while you do a lot of the core work, not outsource completely? Then none of this applies either.

What Do You Do Now?

I know it's hard to find a technical cofounder.

Maybe you already hired a dev shop, and they're promising to deliver exactly what you want, on time, and within budget. What do you do?

Fire them.

You need to ignore sunk costs. Find a technical cofounder, or take what money's left and hire a "founding engineer" to work on it with you full time.

Would you start a restaurant without a chef? Then why would you start a tech company without someone who can build your product?

It's hard enough building a company. Give yourself the best chance possible for success.


When I first heard about TinySeed, I was excited. Venture Capital isn't for everyone, and bootstrapping can feel impossible. It seems like there isn't much in between. I'm excited to see new, innovative ways for founders to get startup capital.

Unicorn Hunting

But as I dug deeper into TinySeed, I came across this in their FAQ:

Traditionally, venture capital has consisted of unicorn-hunting. VCs are looking to fund the next Facebook or Oculus Rift. If a traditional VC funds your business and it gets to $50m in revenue, generating $20m in profit year over year, it’s considered a miss.

This seems naive, disingenuous, or both. Most (all?) angels and early stage VCs would be elated to fund a startup that grows to $50m ARR with $20m profit.

Dan Primack pointed this out succinctly on Twitter:

And the replies to his tweet are a masterclass in understanding VC. In short, VC expectations are related to fund size, check size, and ownership.

As a founder, you should understand this fund math before you a) raise money or b) write off all angel/VC money as bad.

Investment Terms

Here's how TinySeed values your company:

TinySeed invests $120k for the first founder + $20k per additional founder, in exchange for 8-15% equity.

As a solo founder, they'll value your company between $680k and $1.4m pre-money. Compare this to median pre-money valuations from "traditional" angel and seed rounds, which is now around $7M. So you can raise 5-10x more money in exchange for the same equity.

If early stage investors consider 20x return a home run, they'll be very happy to see your $50m ARR "lifestyle business" exit for $140m or more.

If, like TinySeed, the same investors had invested at a 1/10th of the valuation? The resulting 200x return would be an off-the-charts grand slam.

TinySeed may be a great option for some founders. I personally admire much of what they're doing, and might have considered it for Formstack:

  • They're targeting bootstrapped companies, and I bootstrapped for 3 years before raising a small angel round.
  • It's remote, and I started shortly after our first son was born, so wouldn't move across the country to join an accelerator.
  • They're not biased against solo founders, and I was one.

But their terms seem structured just like any angel or early stage VC investment — they give you cash for equity in your company. And at a valuation that might be way below market for your company. And you're required to pay investor dividends in perpetuity if you want to make more than their salary cap.

And they get a participating preferred liquidation preference, which has been absent from clean term sheets for a while now:

If the company sells, investors receive the initial investment back (minus any dividends paid to date), and then the proceeds are divided pro-rata based on ownership.

[UPDATE: This is fixed]

Forcing Growth

The core value prop for TinySeed seems to be the promise that they won't "force growth."

But I personally haven't seen an early stage investor do this. They're focused on making sure the company exists in the next 12 months. Even YC preaches getting to ramen profitable and default alive so you're not relying on investors for continued survival.

Investors don't want you to grow because they like to gamble with the health of your company. They want you to grow because lack of growth is why most companies die.

This is different than the pressure for huge exits, which comes after raising tens or hundreds of millions of dollars from later stage VCs. Especially when you've put yourself in a position where you have to keep raising money over and over again. At some point, the math just gets to a point where you have to become a unicorn to deliver a home run.

But if you're raising a few $100k, and do it with a standard SAFE, you're not giving investors any leverage. There's no board seat, majority ownership, or preferred stock to force you to do anything. And investors will be as happy as you when you build a $50m ARR company.

If you don't need to raise money to build the company you want to build, don't raise money.

Or look to firms like Indie.vc that are structuring funding in a very different way. They apply dividends toward a buy back of up to 90% of investor equity. And dividends are capped at 3x the original investment.

Or look to firms like Lighter Capital that offer debt financing without taking any equity.

But also know that there are "traditional" angels and early stage VCs that you might enjoy working with, and will be aligned with founders. Just raise at a sensible valuation, and build a great business.

Isolate the Pain

I started running frequently a few years ago. I ran my first 5k in 2016, and ran my first half-marathon in 2018.

One of the hardest things I have to do when running is manage my own psychology. Most days, my brain starts telling me it's OK to quit before I reach my goal.

"It's fine. You did well yesterday, take it easy today and make it up tomorrow."

And in a swirl of exhaustion and pain, it's easy to listen.

I realized there's usually only one thing that's physically bogging me down. If I can isolate and eliminate it, the swirl of exhaustion and pain gets a little better.

Is my throat burning? Maybe I just need to take a swig of water.

Is my back hurting? Maybe I just need to adjust my posture.

Have I lost focus? Maybe I just need to play that song that always adds more bounce to my stride.

I see parallels to my time as an entrepreneur. I often found myself in a swirl of exhaustion and stress, nothing going right, wanting to give up. But I had to pause and isolate the pain.

Maybe I just needed to cut enough expenses to give us more runway.

Maybe I just needed to fire an executive that was pulling the team in the wrong direction.

Maybe I just needed to unplug and take a vacation.

Most times, there was one major thing that was bogging me down. And when I isolated and eliminated it, I found a path to keep moving forward.