10 things to know when bootstrapping a B2B biz
Blanditiis voluptas alias occaecati vel in rem. Et itaque aliquam corrupti aliquid minima rerum. Repudiandae et id ratione magnam omnis ex saepe. Doloremque rerum accusantium veritatis unde.
Fundraising is often glamorized. Pitch decks, investor intros, PR moments. But the truth? It’s a full-time job — and once you raise, your job changes. You’re no longer building a business for yourself. You’re building a return for someone else.
Profit changes everything.
When your business generates real cash, you can:
Rand Fishkin (SparkToro) walked away from VC-backed chaos to build a calm, profitable company. Now he serves a loyal audience on his terms, without chasing growth at all costs.
📌 Key insight: Fundraising is a tool, not a strategy. Freedom is the real endgame.
👉 And once you taste it, you’ll never want to build any other way.
We’ve all seen the headlines: "$100M exit!" It sounds incredible — until you break it down.
10 years of grind, 60–80% dilution, taxes, and fees… and the actual payout often disappoints.
Now compare that to owning 60% of a business generating $2M/year in profit. That’s $1.2M every year — and you still own the asset. You’re not waiting for a liquidity event — you’re living it.
Nathan Barry and ConvertKit turned down VC offers and built a $30M+ ARR machine with full control.
📌 Key insight: Sustainable income beats a one-time payday.
👉 The smartest founders aren’t chasing the exit — they’re compounding wealth.
Most startups over-hire and overcomplicate.
The result? Slow execution, unclear ownership, and meetings about meetings.
But a small, focused team of generalists can ship faster, stay closer to customers, and build a stronger culture of ownership.
Pieter Levels runs a portfolio of profitable businesses completely solo — and outperforms teams 10x his size.
📌 Key insight: Bloat is a tax on progress.
👉 Every person you hire should create clarity — not more coordination.
AI is no longer a novelty — it’s a strategic advantage.
It gives tiny teams the power to compete with large orgs by automating support, speeding up content creation, and reducing decision fatigue.
You can generate product descriptions, analyze customer sentiment, launch a landing page, and write an email sequence — all in a few hours, without code.
Small teams using AI are now the most efficient teams in the world.
📌 Key insight: AI doesn’t replace people — it replaces overhead.
👉 If you’re not using it, your competitors are — and they’re moving faster.
Founders love building. But if the math doesn’t work, your product won’t survive.
Before you code a single thing, know your pricing, your CAC, your margin, and how long it’ll take to get to breakeven.
Profitable businesses are designed deliberately — from day one.
Jon Yongfook's Bannerbear grew to $50K MRR because it was built around recurring value and clear pricing, not just features.
📌 Key insight: Don’t just solve a problem — monetize a system.
👉 Revenue should be an assumption, not an afterthought.
Every equity deal comes with strings.
Dilution may feel harmless in the early days, but as time goes on, you realize how much flexibility and peace of mind you gave away.
When you keep ownership between you and your co-founders, you preserve autonomy, alignment, and long-term upside.
Basecamp has shown what’s possible when you own your growth and your future.
📌 Key insight: More equity = more freedom, more leverage, more peace.
👉 Sometimes the best investor is your own margin.
Mass markets look big and sexy — but they’re often crowded and expensive to win.
Niches, on the other hand, are full of unmet needs, ignored customers, and pain points no one else is solving.
SparkLoop started by focusing on one very specific problem — newsletter referrals — and became the go-to tool for creators, fast.
Niche markets are easier to dominate, easier to speak to, and easier to monetize.
📌 Key insight: The smaller the pond, the easier it is to become the big fish.
👉 Obsession wins — and you can’t obsess over everyone.
Most early teams grow headcount faster than revenue.
But smart founders keep things lean, systemized, and tightly scoped until the revenue demands the hires — not the other way around.
Transistor.fm and Fathom Analytics reached six and seven figures in revenue with small, efficient teams and almost no overhead.
They didn’t build big teams — they built big leverage.
📌 Key insight: Small teams build faster, learn faster, and keep more of what they earn.
👉 If it doesn’t scale without people, it doesn’t scale.
Shallow products are easy to copy.
Deep understanding? That’s impossible to fake.
When you deeply understand the customer’s workflow, their pain, and their language, you can create something that feels magical.
SavvyCal didn’t just build another scheduling tool — they fixed nuanced frustrations real users were experiencing, and created a better experience that users feel.
📌 Key insight: Insight is your advantage — not just speed.
👉 Depth builds loyalty, retention, and word of mouth.
You don’t need to blitzscale.
You don’t need to raise $10M.
You don’t need to exit in 3 years.
You just need to show up, keep your burn low, serve your customers well, and let profit compound.
Gumroad grew to $10M+ with one employee — because they stayed focused and ignored the noise.
📌 Key insight: Small, profitable, and consistent beats fast, flashy, and fragile.
👉 If you’re still standing in 10 years, you win.
Freedom > Fundraising
When you’re profitable and own your business, you’re in control.
No pitch decks. No investor updates. No waiting for approval to build.
Instead of chasing capital, focus on cash flow.
Example: Rand Fishkin of SparkToro built a profitable business after leaving a VC-backed one — and publicly shares how much more freedom he has now.
Tools that help:
Everyone’s chasing the $100M exit. But after years of dilution and stress, the end result often isn’t life-changing.
Instead, build a business that throws off $1M+ in profit annually — and still gives you ownership.
Example: The team behind ConvertKit turned down acquisition offers and kept scaling a bootstrapped company now doing $30M+ ARR.
Quick math: 60% ownership of a $2M profit business = $1.2M/year.
That’s recurring wealth. Not a one-time hit.
Too many people = too many problems.
Startups love to hire fast, but lean teams win.
Example: Pieter Levels famously runs multiple profitable startups (Nomad List, Remote OK) as a solo founder.
Everything he does is systemized, async, and low-overhead.
Tools that help:
This is the first time small teams have access to the kind of scale only big orgs used to enjoy.
AI is your co-founder, your intern, your ops manager.
How I use it daily:
Tools:
Before you build a landing page or write code, figure out the money.
Don’t build a product. Build a machine that generates profit.
Example: Jon Yongfook built Bannerbear solo to ~$50K MRR — with profit baked in from day one.
Frameworks that help:
Every time you raise, you lose optionality.
If you and your co-founders can own 100%, or close to it, do it.
Why?
Example: Basecamp raised one small round and never again. They’ve been profitable for 20+ years.
Start narrow. Go deep.
Big markets are sexy, but they’re noisy and expensive. A small group of highly motivated customers is all you need.
Example: SparkLoop started as a tool just for newsletter referral programs. It’s now widely adopted — because it was focused early.
Tip: Ask “Who would immediately pay for this?”
Build for them. Serve them obsessively. Own the category.
It’s not just possible. It’s ideal.
Every extra hire adds cost, complexity, and meetings.
Examples of companies doing this:
Tool tip:
Use Paddle or Lemon Squeezy for payments + taxes so you don’t need a full finance team.
Most people copy competitors.
You go deep on the customer.
Know their real pain. Their workflow. Their context. That depth gives you a product nobody else can easily copy.
Example: SavvyCal didn’t just build “another Calendly” — they dug into power user frustrations and created something genuinely better.
How to get depth:
You don’t need to scale fast to win.
Play the long game with small overhead and deep customer love.
Example: Gumroad hit $10M in revenue with a team of 1 for years.
They didn’t rush. They just kept building.
You’ll win by:
Growth doesn’t always look like headcount. Sometimes, it’s just less chaos and more money in the bank.
.jpg)
Before writing a line of code - figure out your business model
When we mention that Kickdynamic was 100% bootstrapped (not a £/$ of outside investment), we would always get a "wow, that is amazing, how did you do it?".