Ugly Talk Weekly #24

Hi {{first_name | Ugly Talkist}},

One founder watched his company run out of money the same week his girlfriend left him. Another let her store go while she chased a magazine cover.

8 Ugly Talks. 18 founders on stage. Over 2,000 of you in the rooms, across two Tech Weeks in Boston and New York. We distilled it into 3 ugly lessons, each one a mistake somebody already paid for, so you don't have to. Here they are.

Boston Tech Week + NY Tech Week · May 26 – June 6, 2026

The setback. Fresh out of college hackathons, Osama bet brum on consumers, building a "medical tourism Expedia" and hustling to drive patients to clinics himself. The money never came fast enough, and every VC passed on the consumer motion. By the winter break of 2024, the company was out of cash. He spent it broke with no plan, and his girlfriend left him over it.

The comeback. Cornered, he stopped selling to patients and sold the same engine to healthcare businesses instead. The phone started ringing, and brum finally had revenue.

The takeaway: if you can't afford to find out whether the market wants it, you're in the wrong motion. Pick the go-to-market that lets you learn for the price of a phone call, not an ad budget. B2C makes you pay to learn; B2B lets you dial the phone.

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The setback. When the rent on her Aspen store tripled from $11K to $33K, Bonnie let it go without a fight. Her head was in Paris, on the cover of W, on getting Gigi Hadid into her clothes. She lost the store and the real customers who walked through its door, and found out the glamour she chased had never once paid the rent.

The comeback. She rebuilt around the customer she'd been ignoring, and now runs every call through one test, business or ego, and won't outgrow her funding again.

The takeaway: before the splashy move, ask which line item actually pays the rent. The visibility that feels like growth is usually the thing quietly starving it.

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The setback. Kanika built myPeers out of her own experience with mental illness, and since she'd already sold a company to Google, money wasn't the pressure. For two years she optimized for impact and let the business drift.

The comeback. She pivoted from consumers who wouldn't pay to the insurers and enterprises who feel the cost, got disciplined about when to raise, and closed $8.5M.

The takeaway: loving the mission can quietly excuse you from building the business. If your company vanished tomorrow, who would actually miss it? Build for them.

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UGLY TALK:

WHAT INVESTORS DON’T TELL YOU ABOUT FUNDRAISING

WED 24 JUN 6:00 PM – 8:00 PM EST
Silicon Valley Bank -New York

Most founders hear "no." Few hear why.

Join a panel of early-stage investors as they unpack the hidden reasons deals don't happen, from timing and traction to story gaps and red flags.

The conversation investors usually have after the founder leaves the room.

See the full calendar »

Don't' just sit on the sidelines