YI Coached Five Funded CEOs This Quarter. They All Had the Same Disease.
Over the past few months I sat down, one on one, with the CEOs of five funded companies: a rent-payment fintech, a dental supply-chain platform turned fintech, an agri-tech company detecting pests in palm trees, a health-tech company that can screen for six cancers from a home blood kit, and an equity-management SaaS taking on the market leader.
Different industries, different stages, different founders. Same disease in every single room: their go-to-market strategy was built for chapter 10 while the company was living chapter one.
This isn’t a marketing problem. It’s a CEO problem, because sequencing is the one decision nobody else in the company can make for you. What follows are five real go-to-market strategy examples, what each mistake looked like from inside the room, and what it costs.
Go-to-market mistake 1: Solving your third problem before you’ve dominated your first
The dental platform founder gave me an honest history of his company. They started as a B2B marketplace for dental supplies. Then they discovered clinics needed financing, so they became a financing aggregator. Then they saw the patient side was bigger, so they built buy-now-pay-later for treatments. Now they’re signing a bank partnership, launching a co-branded healthcare credit card, exploring crypto payments, discussing an LLM partnership with a university, and considering screens in hospital lobbies.
Each move had logic. Together, they had none. When I asked him which business he actually wanted to be in, helping clinics or helping patients, he couldn’t answer cleanly, and neither could his marketing team, which is why their website said “healthcare ecosystem” and their ads said “a milestone moving healthcare forward.” Nobody buys an ecosystem. Nobody cares about your milestone.
I told him what I tell every founder who’s discovered a second mountain: the only reason you found the struggles in problem one is because you went deep in it. The shiny object next to it looks easier only because you haven’t climbed it yet.
Here’s the kicker. His existing business had real numbers: 30 to 40 percent market penetration, over a thousand clinics, millions a month in financed volume. That’s a moat. His fastest path to the new product wasn’t a new audience, a new app, and a new brand. It was the clinics already answering his team’s calls every week. Your least-friction go-to-market is almost always the customer you already have. Opening a new category of audience, building trust from zero, is the most expensive move in business, and CEOs keep choosing it because it feels like progress.
Go-to-market mistake 2: Your best asset is buried, because you fell in love with the how
The health-tech CEO spent twenty minutes walking me through his “digital twin” technology. Blood samples, 100,000 biomarkers, AI models, a companion watch, a portal, two websites, two brands. Impressive. Genuinely.
Then I asked the team what their single biggest value was, and all three founders said the same thing without hesitating: we can screen for six types of cancer, non-invasively, from home, for a fraction of what anything comparable costs. Two of those cancers are the most common. Four are among the most lethal precisely because they go undetected.
That sentence was nowhere near the front of anything. It was buried seven layers deep behind twinning language, because the founders were in love with the how. I told them straight: nobody wakes up wanting to clone themselves. Anyone who has lost someone to cancer is your first customer, and you’re greeting them with a technology diagram.
This is the founder’s curse of knowledge, and it shows up in every deck I read. You project your obsession with the mechanism onto a market that only cares about the outcome. Twinning is the vehicle. Living is the destination. The CEO’s job is to make sure the company sells the destination, because everyone below you will default to selling the vehicle they built.
The same CEO was also waiting, month after month, on a single investor. I pushed him toward a different sequence: structure the offer with real scarcity (his lab genuinely can only process 150 clients a month), open a paid waitlist, run a crowdfunding campaign for awareness, and walk into the next investor conversation with a thousand people paying $100 a month. A waitlist of paying customers is a stronger fundraising asset than a pitch deck, and it’s fully within your control while the investor is not.
Go-to-market mistake 3: Pricing secrecy and an offer with no structure
The agri-tech founder had a working product, real demand, and near break-even economics. His growth blocker was self-inflicted: he kept his pricing secret and negotiated every deal one-to-one on WhatsApp, because he charges different customers different amounts and didn’t want them comparing notes.
I get the instinct. But hidden pricing is one of the biggest adoption killers in any B2C or SMB motion, and the fix isn’t transparency for its own sake. It’s offer architecture. He was selling the same device to a retiree with 500 palm trees and to a commercial farm with 20,000, at different prices, with nothing structurally different between them. Of course he had to hide the price; the price had no logic to stand on.
The fix: split the buyers, then build the ladder. Under 500 trees, one device, one price, published. Over 5,000 trees, multiple devices plus dashboard, analytics, hotline support, and training, at a premium the added services justify. Now the higher price isn’t secrecy, it’s structure. Now his site can qualify and disqualify buyers on its own instead of every deal routing through the founder’s WhatsApp. A CEO negotiating individual device sales by text message is not a sales strategy. It’s a bottleneck with a title.
Go-to-market mistake 4: Spending on reach before the machine can convert it
The rent-payment fintech wanted to talk about ad campaigns. They were burning $30 to $40K a month, pre-Series A, paying an agency $1,800 monthly for social banners, and planning their first big paid push. I told them to save the money. If you run ads today, a hundred landlords will not call you tomorrow, because the infrastructure that converts attention into trust, the owned media, the testimonials, the founder visibility, the clear buyer-specific message, doesn’t exist yet. Ads pour water into a leaky bucket at a startup’s most expensive moment.
The equity-management SaaS had the sophisticated version of the same issue. They were splitting effort across five channels: AI outbound doing 20,000 automated emails a month, manual SDRs, founder-led sales, partnerships, and influencer deals. The CEO had the data in front of him: the AI channel was expensive per demo and drowning in the same spam saturation everyone else’s AI tools create, while one human SDR was outperforming the entire robot army. The partnerships everyone loved talking about converted at nearly zero. His instinct, kill the AI spend and hire a second SDR, was right, and he half-apologized for it because it felt unfashionable. It shouldn’t. A high-trust product, where someone is putting their company’s financial structure on your platform, is not bought from a cold mass email. It’s bought from a person, after content and community have done the warming. Channel discipline is unfashionable and correct.
There’s a benchmark worth knowing here: the Small Business Administration’s guidance is 5 to 10 percent of top-line revenue, not profit, reinvested in marketing. Most of these founders were far below it while simultaneously overspending on the wrong things. The problem was never the budget. It was that spending had no sequence.
The pattern, and the fix
Chapter one is always the same three moves, and they’re cheap:
One buyer. Not “landlords, tenants, and merchants.” Not “clinics and patients and banks.” One. The one who owns the transaction. Everything else is a benefit you mention, not an audience you build for. When one of the fintech founders told me the hardest part is that founders dilute focus until they learn the hard way, I told him what I believe: it’s different when you’re in the water versus on the boat. That’s what advisors, boards, and quarterly accountability are for. If I hadn’t failed with companies like Sidecar, which offered riders fifteen features when they only wanted one, I couldn’t spot it in an hour.
One sentence. If your co-founders can’t say what you do identically in under ten words, your market has no chance. “The best way for property owners in Dubai to collect rent.” “Screen for six cancers from home.” “Helping founders manage equity.” When we changed one word for a genealogy platform we ran campaigns for, from “download the app” to “upload your family tree,” the whole campaign’s performance flipped. Words are the cheapest leverage a CEO will ever buy.
One proof loop. Your existing customers are your go-to-market. Testimonials, referrals (at Lyft we paid drivers just to be online in new cities and paid referral bonuses that turned every user into a recruiter), case studies, and founder visibility. All nearly free. All compounding. All ignored in favor of the next product line.
The uncomfortable truth for a CEO is that chapter one is boring. Credit cards and LLM partnerships and new markets are more fun than calling your first hundred customers and fixing your homepage sentence. But the companies that get funded, and the ones that survive, are the ones whose CEO had the discipline to stay in chapter one until it was won.
What are you building right now that belongs in chapter 10?
Roy Abdo is the founder and CEO of Digital Revamp, an executive thought leadership and digital communications agency operating across Washington DC, Dubai, and Beirut. He has advised companies from Lyft and Turo to the World Bank and global research firms, and coaches funded founders on positioning, go-to-market, and sequencing.
CTA: Want an outside read on your sequencing before your next raise or launch? Book a session with Digital Revamp.