What I Wish I Knew at 24 When I Co-Founded SinglePlatform

We started building SinglePlatform when I was 24. I had a founder I trusted completely, a problem I could see clearly, and no meaningful understanding of what I was about to go through. Twenty-two months later we sold to Constant Contact for $100M.

I've been asked to reflect on that experience more times than I can count, usually by founders who are earlier than I was. What I know now is that the version I tell at dinner is the right one and the version I tell myself is a different story. The dinner version emphasizes the outcome. The honest version includes the mistakes that happened between founding and exit that I'd never have made with better information going in.

Here's the briefing I wish someone had given me.

Your Speed Advantage Is Real, Finite, and Burning Right Now

Paul Graham has written about this more clearly than anyone. In his essay "Do Things That Don't Scale," he argues that the defining advantage of an early-stage startup isn't technology or capital. It's the willingness and ability to do things that a larger company structurally cannot. Speed is the most valuable version of that advantage.

A startup can make a product decision in a morning that takes an established competitor three months of roadmap prioritization, legal review, and executive alignment. It can sign a partnership this week that a company with $100M in revenue won't even evaluate until next quarter. It can change direction on Tuesday because someone heard something on Monday. The entire strategic posture of an early-stage company should be built around exploiting this window while it exists, because it closes.

It closes as headcount adds process. It closes as investors get more involved in decisions. It closes as the company accumulates the organizational memory and defensiveness that comes with any institution trying to protect what's working. You cannot recover it. And most early-stage founders squander it by running deliberate processes designed for a company ten times their size.

At SinglePlatform, we made one explicit operating principle out of this. Jeff Bezos articulates a version of it in his 2015 shareholder letter as the distinction between "one-way door" and "two-way door" decisions: most decisions are two-way doors, reversible if you're wrong, and should be made fast with available information. A small number are one-way doors and deserve real deliberation. The mistake most founders make is treating every decision like a one-way door.

We shipped things that weren't perfect. We closed deals that were directionally right and needed to be renegotiated later. We moved. The cost of being wrong and correcting was almost always lower than the cost of being right six months late. I've never seen a founding team regret moving too fast. I've seen dozens regret waiting for certainty that never arrived.

Hire for the Company You're Becoming, Not the One You Are

The most expensive personnel mistakes I made at SinglePlatform were people who were right for the company at the moment I hired them and wrong for the company six months later. Early-stage companies evolve faster than most people can grow with them. The skills that get you from zero to one are not the same skills that get you from one to ten.

The scrappy generalist who is perfect at $1M ARR can become a ceiling at $10M. The operator who thrives in ambiguity can struggle when the business needs structure. This isn't a failure on their part. It's a physics problem. The job description changed underneath them faster than anyone could adapt.

Ben Horowitz covers this in The Hard Thing About Hard Things under what he calls the scale problem: "A person who is doing their job well at a company with 50 people might be failing at a company with 200." His advice is to hire slightly ahead of where you are, which I'd extend to: think explicitly about what the role looks like in eighteen months, and hire for that version, even if the immediate version is simpler.

The other half of this lesson is harder to execute: have the conversation early when someone has outpaced their role in either direction. Before it's obvious to everyone. Before the team has compensated around it. Before the person has stopped believing the company sees them clearly. The conversation is never as difficult as the six months of ambiguity that precede it.

The Credential Is the Company. The Career Is the Relationships.

The strangest thing about selling a company in your mid-twenties is how anticlimactic the moment is. The wire hits. The next morning the same problems exist that existed the day before. The same people need managing. The same product decisions are unresolved. You're expected to show up as if something fundamental changed and also as if nothing did.

What I know now that I couldn't see then: the headline number matters for about six months. The reputation you built for how you operated, whether you were honest with people, whether you made hard calls clearly, whether you treated people the way you'd want to be treated when it was your turn on the receiving end, that matters indefinitely.

Almost everyone who was part of the SinglePlatform story is still in my life in some meaningful way. Some are founders I advise. Some became investors in things I care about. Some are just people I call when something is hard. The company became a line on a resume. The relationships became the infrastructure for everything that came after.

Build that way from the beginning. The outcome tends to take care of itself.