By Meka Asonye
Think of the framed first dollar bill you see behind the counter at your local mom-and-pop shop or restaurant, an iconic symbol of someone bringing an idea to life. For founders building B2B companies, getting to that first $5 million in ARR represents a similar milestone — albeit with a few more zeroes behind it.
But something too many gloss over, in my view, is that the path to that first few million starts long before the first dollar comes in the proverbial door. Too often, technical founders furiously build before coming up for air, telling themselves “We'll figure out the commercial stuff later.” The pressure to move quickly on the product front can cause founders to skip the critical early work of laying strong commercial foundations.
This temptation to focus solely on building will likely only grow more pronounced in an era where AI makes it possible to ship faster than ever. Founders can now go from idea to launch in record time. And we’ve all seen the headlines about AI companies that have reportedly sprinted to their first several million in revenue in absurdly condensed timeframes, with social posts touting growth curves that resemble almost vertical lines.
But the jury is still out on how sustainable these growth engines will be — a fast start off the blocks doesn't guarantee staying power, and we’ve already seen just how quickly competitors can crop up and moats can dissolve. What looked like near-instant product-market fit might later reveal itself as temporary fervor, with high churn rates lurking around the corner. When it comes time for renewal, the question is: Did you truly become part of the workflow, or were you just a shiny object worth experimenting with?
Reaching extreme PMF and unlocking lasting commercial success — the kind that compounds year after year — remains incredibly challenging. That’s why here at First Round we get particularly excited to team up with founders who’ve gone unreasonably deep — not just in lines of code, but in excavating many layers into the market, their customers, and their potential path to building an enduring business.
It’s never too early to think about the commercial side of your business — getting to your first few million starts long before the first check clears. It begins by choosing the right market, the questions you ask in customer discovery interviews, and the ICP you land on.
The real question isn’t just how fast you can sprint to your first few million in ARR. It’s whether you’re building a GTM engine that can sustain the growth, even after the hype dies down. In my experience (and what I tell every founder I meet with), neglect of the commercial side of the ledger is a recipe for pain down the road. Put simply, this isn’t “Field of Dreams,” and the “build it and they’ll come” strategy usually doesn’t pan out in the long run.
You’ll have to forgive the clunky baseball metaphors — my non-linear path to becoming a partner at First Round started out in the “Moneyball” world of working on player development and baseball operations for the Cleveland Indians. But it was my time at Stripe as one of the first account executives that would more directly shape my perspective on what it takes to build enduring companies.
As Stripe scaled from 250 to 2,000 people and began moving upmarket to land enterprise logos, I headed up our efforts to 10x our Startup/SMBs business. This meant everything from launching outbound sales and building a customer success function to developing distribution partnerships and standing up new offices. Later, as VP of Sales and Services at Mixpanel, I led a 100-person global team, owning the customer lifecycle from first website visit to renewal.
These experiences showed me that early commercial choices, even ones that feel incidental, compound over time — both positively and negatively. Now as an investor at First Round, I partner with founders further upstream at the very beginning of their journeys — often pre-revenue — tackling the full range of early-stage challenges: What should we build first? Who's the right customer? How do we price this? When do we start hiring?
These are questions that every founder must grapple with, whether they’re building straight down the fairway B2B SaaS like automating startup compliance, literal rocket scientists building better satellites or creating more effective 911 tech for first responders (and I’m fortunate enough to be partnering with each of these builders). The early decisions can ripple through a company’s entire growth trajectory, far beyond those first few customers and the first few million.
Working closely on these very early founders and hunting for good resources to recommend specifically for the journey from 0 to $5M, what I noticed is that most early GTM advice floating around out there misses the mark in one of two ways: It’s either too broad, doling out platitudes that apply to everybody but help nobody, or too specific, focusing on an already-successful company’s path to millions in ARR, which may not be applicable for most other startups. There's surprisingly little tactical guidance that hits the sweet spot in between.
My goal with this series is to attempt to fill that gap (and it’s heavily inspired by the work my friend and fellow First Round Partner, Todd Jackson, has undertaken these past few years by sitting down with founders of top startups like Airtable, Vanta, Gong and Replit to diagnose precisely how they found their paths to product-market fit).
I’m not aiming to present some kind of universal formula for early GTM efforts — those are few and far between when it comes to startups. Instead, I hope to surface concrete patterns and practical frameworks that still-very-early-days founders can apply right away, tweaking to suit their unique circumstances.
That’s why we’re taking a slightly different format here. Instead of deep-dive profiles on how one company cracked the code on GTM, in each installment in the series, you’ll hear from a chorus of different voices to provide a wider range of perspectives — from technical founders who had to learn sales from scratch to early GTM hires who helped scale today's iconic companies (and clean up the messes). Some of these folks are well past that $5M milestone, others are currently working towards it now.
My goal is to unearth the hard-won lessons that founders and first sales hires learn (often painfully) during the 0 to first few millions process but tuck away in the corners of their brains. We'll examine not just what worked, but why it worked, diving deep into the nitty-gritty details that often get glossed over in startup lore, like how to approach those first customer calls (do you sell right away or take a softer approach? When should you demo?), warning signs that PLG isn’t a good fit for your buyer, when to consider moving upmarket and trying your hand at selling to enterprise, and what are the signals that it’s time to set aside founder-led sales and hire your first salesperson.
I hope you’ll follow along (and send in any ideas for future topics or guests to @BigMekaStyle on X).
With that, let’s dive into the first article in the series, all about how founders can overcome their fear of the “sales boogeyman” and embrace founder-led sales.