Founder Intensives

When you’re stuck, 90 minutes can change everything.

A laser-focused session on your biggest roadblock, critical decision, or knowledge gap — so you know exactly what to do next.

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Bruce C, a happy Startup Distillery client

"Diane is a straight shooter who isn't afraid to tell it like it is."

“My favorite part of our intensive was getting clear on what we’ve done right, what we’ve done wrong, and what we need to do next to kickstart momentum.”

Bruce Caughman

GAME VODKA

What is a Founder Intensive?

You’ve been trying to figure this out on your own. Maybe for weeks, maybe for months. You’ve listened to podcasts, read everything you can find, attended events.

Everyone has an opinion — investors, other founders, the media — and everyone sends you in a different direction. You’re not short on advice. You’re short on knowing what leads to expensive mistakes — some you can recover from, some you can’t.

Building a business is a completely different skill set. And when you’ve never done it before, there’s no way to filter what you’re hearing. So you keep spinning.

You can’t read the label when you’re inside the bottle.

A 90-minute intensive is designed to cut through all of that — no cheerleading, no bias, just the questions you haven’t thought to ask yourself. That’s how we get to the real issue — the one that’s actually blocking you — and bring it to the surface, often for the first time.

This is a one-shot, high-impact session. No ongoing commitment. Just concentrated problem-solving in a single session. Some founders book one and that’s all they need. Others come back whenever they hit a wall.

Here’s what 90 minutes can do.

Walk in stuck. Walk out knowing exactly what to do next.

01

Thought he needed a co-founder.

The setup: Just launched his own app. 10 years building AI systems at Apple, Expedia, Stitch Fix.

His problem: He didn’t have marketing, growth, or fundraising experience — and everyone around him kept telling him he needed to find a co-founder. He didn’t actually want one. But when every investor and founder you talk to says the same thing, you start to believe it.

The real problem: When I asked why he wanted a co-founder, he said he didn’t have marketing or growth experience. I pushed back. He didn’t need a partner — he needed to hire for the skills he was missing. You don’t need to be the expert in every part of your business — you need to understand enough to ask the right questions, then hire people who can execute.

My recommendation: Stop looking for a co-founder. Hire the expertise instead. Taking on a co-founder is like getting married — and you’re giving away equity, control, and your vision to someone whose goals may not always align with yours.

The shift: From months of searching for a co-founder he didn’t need, to keeping his equity, hiring for the gap, and trusting his own gut.

02

Thought banks were his only option.

The setup: Building an aquafarm on the South Side of Chicago. Needed $300K for property and equipment.

His problem: Banks wouldn’t lend to him without a year of operating history — and he couldn’t launch without outside funding.

The real problem: He told me he had no financial projections. When I asked how he’d set his pricing, he said he’d walked into a few stores and copied what competitors charge. That’s not pricing — that’s guessing. And the $300K? A rough estimate based on 20-year-old numbers. He didn’t know what he actually needed because he’d never done the math.

My recommendation: Stop calling banks. Get real numbers — line item by line item — so you know exactly what you need. Then pursue funding. Consider other sources: SBA loans, grants, aligned investors — options he didn’t know existed until we talked them through. The shift: He came in thinking banks were his problem. He left knowing the numbers have to come first — and he has funding options beyond banks.

03

Knew he should “know his numbers.” Had no idea what that meant.
The setup: Six months into building his business. He was making decisions about pricing, expenses, and how much funding to pursue — and realized he was making every one of them blind. His problem: Everyone kept telling him to know his numbers and he’d nod in agreement. One day he was talking to another founder and realized he was just nodding along without understanding. That’s when he realized, “I can’t keep faking this.” The real problem: He didn’t know the basics — like the difference between a P&L and cash flow projections. And why would he? Nobody teaches you this — not in corporate, not anywhere. But the gap is dangerous. A business can be profitable on paper and still go bust by running short on cash. Without understanding both, every financial decision he was making was a guess. What he needed to know: You don’t need to become a financial expert — but you do need a working knowledge of what each spreadsheet tells you. How to price for profit, how much money you need to reach profitability, and how much runway you have. The shift: He came to me not knowing what any of these spreadsheets are or why they matter. He left understanding all three — P&L, Cash Flow, and Sources & Uses of Funds — what each one tells him about his business and how to use them. Once you do, you stop guessing.

04

Couldn’t close despite a killer track record.
The setup: 30 years in banking delivering million-dollar projects. Led teams of 90. Closed deals across continents. Her problem: She kept pitching prospective clients and not closing — kept striking out or getting lowballed, despite an undeniable track record. The real problem: When I asked how she pitches, she gave me this: “I build consensus, streamline operations, and manage complex transactions.” Then I pushed. And out came: “Projects hemorrhaging time and money — because no one owns the problem. I fix that. And then deliver.” She had the goods the whole time. She just wasn’t leading with them. My recommendation: Stop leading with credentials. Lead with the pain — where they’re hemorrhaging time and money in their operations. Once you know what the pain is, press your thumb on it so hard that the reaction is visceral and immediate — and they come to you. The shift: A complete shift in how she positions herself, how she sells, and how she shows up.

More examples.

Thought they had a funding problem.
The setup: Two products in the green/sustainable gardening space — one commercial, one consumer. Commercial: industry relationships and a licensing path in place. Consumer: already successfully piloted. Their problem: They wanted to go all in on the consumer product — that was the dream. But it was capital intensive, and they didn’t have the money to manufacture at scale. (The commercial product had low startup costs and the first project would pay for itself.) The real problem: When I asked why they weren’t leading with commercial, they went quiet. They’d been so focused on the consumer product that they never considered using the commercial product to fund it. A much easier and faster funding option. My recommendation: Launch commercial first. Phase 1: License the technology to companies that already have the infrastructure and suppliers. Use that revenue to fund Phase 2: the consumer product. The shift: They came in thinking they needed outside funding — and were ready to drop the commercial product. They left realizing that’s what can fund everything else.
Thought he knew who his ideal customer was.
The setup: A tailgate kit company — everything you need for game day in a box. Had a product he’d already tested and was ready to take to market. His problem: He’d been trying to sell to “sports fans” and couldn’t get traction. The product was strong — everyone who tried it loved it. But he couldn’t get retailers to bite and couldn’t figure out why. The real problem: When I asked who his ideal customer was, he said, “sports fans.” I pushed back. What age? How often do they go to games? Burgers off a disposable grill or brisket from a smoker? A 25-year-old tailgating with buddies and a 50-year-old season ticket holder are looking for completely different things — different budgets, different habits, different messaging that resonates. “Sports fans” isn’t a target market — it’s half the country. My recommendation: Figure out exactly who your ideal customer is first. Pick one fan — and speak directly to them. Then build a real customer base and expand from there. Once you do, your messaging sharpens, your marketing has a target, and retailers know exactly who they’re selling to. The shift: He came in sure he knew his customer. He left understanding that “sports fans” was the reason nothing was working — and that his business is dead in the water until he knows his customer so intimately that everything he does resonates with them. They see his product and feel like it was made just for them.
Thought they had a sales problem.

The setup: A sports-themed beverage. They’d been trying to get their product into retail for months. Doors kept closing — but an NBA team wanted to partner with them.

Their problem: They were focused on how to get back on shelves. They assumed the issue was their sales approach — the pitch, the positioning, getting the word out.

The real problem: As we talked through their history, they let something slip that changed the entire conversation: their product had already been on shelves. They’d created demand through pure hustle. Stores were calling for more product. But… they couldn’t produce enough, so they were kicked off shelves. They had done the hardest parts — getting on shelves and an NBA team asking them to partner — most founders would kill for just one of those. And they lost both because they couldn’t fulfill demand.

My recommendation: The question isn’t “how do we get back on shelves?” — it’s “why did we get kicked off in the first place?” Focus on your supply chain, production capacity, and what it actually takes to meet demand before you create it again.

The shift: They came in focused on sales. They left understanding that the real problem was operations — and knowing exactly what needs to be in place before they’re ready to knock on doors again.

Thought VC was her only path to funding.
The setup: Recently launched a baby sleep app. Already on her second startup idea after scrapping her first. Her problem: She assumed VC was how startups get funded. She was already thinking about how to approach investors. The real problem: She had no revenue, no traction, and no leverage. When she brought up VCs, I stopped her and explained that raising VC at that stage means negotiating from the weakest possible position — and means giving up more equity and control than if she waits until she has leverage. My recommendation: Don’t raise VC now — maybe not ever. Build revenue first through strategic partnerships and organic growth. Prove traction. If you need outside capital later, you’ll be negotiating from a position of strength, not weakness. Founders who build revenue first often fund their own growth — and keep far more of their company. The shift: From assuming VC was how startups get funded, to understanding that venture capital at that stage would actively work against her — and that revenue is the real leverage. She left saying it was a million-dollar session — because she’d been about to spend months chasing the wrong thing.
One conversation changed everything.

Every one of these founders had been sitting with their problem for weeks. Some for months.

They weren’t missing effort or smarts. They were missing someone who could see what they couldn’t.

Ready to get unstuck?

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