Over the past year, my co-founders and I raised nearly half a million dollars in venture funding for our freight-tech startup. It was gritty. Dozens of pitches. Hundreds of rejections. A crash course in storytelling, psychology, and stamina. As we prep for our next round, I realized something: fundraising isn’t a one-time performance—it’s a craft. One you have to sharpen before you need it.
So I went deep. For the last two months, I’ve studied everything I could find—courses, decks, articles, investor memos. I sat in on VC panels, decoded how they think, and got coached by Frank Erschen—Canada’s top startup pitch advisor. This isn’t just a guide for beginners. It’s a tactical operating manual for myself, so I never forget how to raise with clarity, speed, and control. If you’re an early-stage founder trying to break through, this one’s for you.
1 - Pick Your Game (Founders Build for Outcomes)
— Know what game you're playing before you try to win it.
Before you step into the arena of venture capital, you need to answer a hard question with surgical precision: What game are you actually playing?
This isn’t philosophical. It’s foundational. Because raising capital isn’t a strategy—it’s a consequence of choosing a particular kind of outcome. And if you’re not honest about the outcome you want, you’ll find yourself on a treadmill that you didn’t sign up for.
Let’s break it down.
The Three Games Founders Play
Every startup founder is subconsciously choosing between three games:
- The Lifestyle Game: You’re building a cash-flowing, freedom-oriented business that lets you work from anywhere, provide for your family, and live life on your terms. You’re optimizing for control and profit, not scale.
- The Indie Scale Game: You want growth—but you're bootstrapping or funding growth through revenue. You care about solving a real problem in a niche market. You're building a base-hit company that can make $1M to $10M a year with high margins.
- The Venture Game: You’re chasing massive outcomes. You’re building a company that could be worth $100M+ or more in 7-10 years. You’re okay giving up equity and control in exchange for speed, scale, and a shot at outsized impact.
Here’s the kicker: all three are valid—but they require different mindsets, skillsets, and capital structures.
Don’t fall into the trap of assuming that VC money is some kind of trophy. It’s not. It’s a tool, and if you use the wrong tool for the job, you’ll break the whole damn machine.
Let’s take a look at how this plays out in real life.
Example #1: The Indie Hacker Who Knew the Game
Courtland Allen, the founder of Indie Hackers, knew from day one that he wasn’t building a VC rocketship. He was building a community and media brand that supported independent entrepreneurs. No blitz-scaling, no burn rate insanity.
He sold Indie Hackers to Stripe within two years—without raising a dime. It was a strategic acquisition that gave Stripe access to a key audience and gave Courtland what he wanted: autonomy, stability, and reach.
He didn’t try to raise VC money because it didn’t fit the game he was playing. That’s the clarity most founders lack.
Example #2: The Visionary Who Picked the Big Game
Melanie Perkins, co-founder of Canva, had a clear vision: democratize design. She wasn’t building a small tool or a boutique software company. She was building a platform for everyone.
She pitched over 100 investors and got turned down repeatedly. But she kept refining the vision. She was playing the venture game. Today, Canva is worth over $25 billion, and she still controls a majority of the company.
She didn’t give up when it got hard, because she had chosen a game worth suffering for.
How to Choose Your Game (A Founder Decision Matrix)
Use this decision matrix to calibrate your direction before you waste time chasing the wrong capital:
| Question | Lifestyle Game | Indie Scale Game | Venture Game |
|---|
| What outcome do I want? | Freedom, cash flow | Niche domination, profit | Hypergrowth, market leadership |
| What's my time horizon? | 1–3 years | 3–5 years | 7–10 years |
| How much capital do I need? | <$50K | <$500K | $1M+ |
| Am I okay giving up control? | No | Maybe | Yes |
| Do I want to manage people? | Prefer not to | Small team | Yes, big team |
| Am I solving a mass-scale problem? | No | Maybe | Definitely |
If you check more boxes on the right column, you’re ready for the venture game.
But even if you’re all-in on the venture path, you need to realize that VCs are betting on outcomes, not intentions. The goal is to build something that can return their fund. That means your vision, market, and model all have to show asymmetry—the chance to turn $1 into $100.
The Psychological Cost of the Wrong Game
Here’s what no one tells you: choosing the wrong game will make you miserable.
If you’re a lifestyle founder pretending to be a VC founder, you’ll drown in pressure you never wanted.
If you’re a VC founder who’s trying to bootstrap because you’re afraid to ask for money, you’ll grow too slowly and die in the desert.
The game you choose shapes your psychology, your schedule, your sleep, and your soul. Choose wisely.
The Founder Fit Test
Before you even touch a pitch deck, ask yourself the following:
- Am I building something that can realistically become a $100M+ company?
- Do I want to manage the pressure and expectations that come with VC money?
- Am I ready to give up ownership and control in exchange for speed and growth?
- Can I tell a clear, credible story about how this company becomes a category leader?
If the answer is no to more than two of those, pause. You may be playing a different game than you think.
What VCs Want (Hint: It’s Bigger Than “Traction”)
VCs are not banks. They don’t care about your spreadsheet or how clean your code is. They’re betting on velocity and vision.
They want to know:
- Can this founder attract other talent?
- Can this product dominate a big, growing market?
- Can this brand become iconic?
- Can this company 10x from where it is now—in the next 18 months?
They don’t fund puzzles. They fund bets. You are the bet.
Homework for Founders Before Raising a Dime
Before you send a single investor email, do this:
- Write a one-page vision doc. Where is the world going, and how is your company shaping that future?
- Define your founder archetype: Are you a builder, a visionary, an operator, or a hybrid? What are you missing?
- Build your personal board of advisors. Even two smart people who’ve raised before can change your trajectory.
- Talk to 3 founders who’ve raised. Ask what they’d do differently. Listen carefully.
In Closing: Play Your Game, Not Someone Else’s
The most dangerous thing a founder can do is confuse ambition with alignment. Just because others are raising millions doesn’t mean you should.
VC is gasoline. If you’re not already on fire, it won’t help. But if you’ve got that spark, that friction, that traction... VC can take you to orbit.
Pick your game. Play it with everything you’ve got. And when the moment comes to raise, you’ll be ready—not because you followed a script, but because you wrote your own.
2 - The VC Game: Understanding How the System Works
— You can’t win the game if you don’t know the rules.
