Freedom, purpose, and 30 years in business: Simon Squibb's masterclass on starting, building and selling companies

Simon Squibb has built 19 companies and invested in 78 startups over 30 years. People have offered him £10,000 for a single day of coaching. He says no and gives the knowledge away for free instead. This article is a condensed summary of his open masterclass — from how to start with no money to how to sell a company — in a format you can read in 15 minutes and apply immediately.

A recurring theme: the school system isn't built to make you free. It's built to make you employable. Much of what follows runs against that current.

How to start with no money

A business doesn't start with an idea. It starts with a feeling — that something needs to change. Then you ask: what do I love to do?

Forget "find a market gap". Simon launched Fluid into a sea of 500 already-established marketing agencies in Asia. It didn't win because it was new — it won because Simon was obsessed with marketing. There is no work-life balance. There's only syncing your life to your business.

Write two columns:

What I love doing → get really good at it
What I don't love doing → outsource it

School taught you to get better at what you're bad at. That's wrong. Get obsessed with what you love — that's where the idea begins.

Need a partner? Find someone whose strength is your weakness (Simon teamed up 50/50 with a designer who translated his marketing ideas into visuals — that became the springboard for what was eventually sold to PwC).

Three steps:

Execution. What's the simplest thing you can do to bring the idea to life? Podcast, blog, LinkedIn, a first photo online. Don't make it hard.
Revenue model. Not always obvious on day one. A photographer who only charges per hour limits themselves. Experiment. Fluid didn't bill hourly for marketing — they took a percentage of the result.
Purpose. If it's only about profit, every employee will demand more money and every customer will demand a lower price. With a purpose bigger than yourself, you stop managing people — you manage the purpose.

How to win: delayed gratification + culture + luck

Three levers:

Delayed gratification. Simon's first Fluid client got the work for free. They stayed for 16 years and referred more. Facebook, Instagram, Google, YouTube — all had almost no revenue for years. They built value first.
Culture eats strategy for breakfast. Be customer-centric as a culture, not a slogan. People want value, not to be milked.
Luck is hackable. Be persistent (you have to outlast competitors), know your destination (what is your definition of success?), and take risks. The lie "harder work = more luck" is just a lie — if true, every nurse would be a millionaire. Risk-taking is what correlates with success.

The secret behind it all: be willing to lose everything. It's a marathon, not a sprint.

How to lose (and why you must learn to)

School taught you that an A grade is success. Wrong. Learning to lose is success. Simon says he'd never have become rich without losing £1M on a comic book company.

Don't let things own you
Drop the short-term ego (right car, right watch, wrong yardstick)
Love being underestimated — it's a superpower
80% of A students end up working for D students because A students are too afraid to lose

Build an internal ego: you know where you're going.

Mind map, not business plan

Business plans kill companies — they're linear and lock you in. A mind map is liquid and lets you pivot. How:

Centre: your hobby / what you love
Branches: the business concept
Sub-branches: podcast → network → brand partners → app → team → products → merchandising → ...

When you draw a mind map of "free Humanity" four years ago — and four years later you actually launch the candy line "Buzz's" that was a tiny branch out on the edge of the map — you understand why mind maps beat business plans. You saw the opportunity in advance.

Nobody sells mind map templates. That's why nobody teaches it.

Find your purpose

School asked you: what do you want to be when you grow up? Wrong question. The right question is: what problem do you want to solve?

What problem has affected you?
How would your life match that purpose?
You don't have to do it alone — partner up (1+1 = 11)

Often the gap between your current life and your dream life is just 3% — a baker working for someone else is already almost there; they just need to take the step and own it themselves.

Find a co-founder

Simon prefers 50% of a business he loves to 100% of a nightmare. Having a co-founder is like having a gym partner — accountability skyrockets.

Steps:

Write down exactly what you love and hate doing
Find someone whose strength is your weakness
Same moral code is non-negotiable
Detail what the ideal person looks like (red car theory — if you don't look for it, you won't find it)
Post that you're looking — LinkedIn, cafés, everywhere

Simon's moral-code test: "You get an amazing life for 40 years — private jet, three houses. But on your 70th birthday you're exposed as a financial fraud. Do you take the deal?" Half say yes. Don't work with those people.

How to sell

Sales is a system. Anyone can learn it.

Sell the sizzle, not the steak

Steve Jobs never said "this phone has an Intel processor". He said it was for those who want to change the world. Sell the transformation, not the spec sheet. At Simon's old agency Fluid, the accountant was the best salesperson — because she could tell outcomes ("we saved a company from bankruptcy", "we made one client an extra £1M a month") at lunch with her CFO friends.

The three-step method

Most people skip straight to step 3. That's the mistake:

Do they need you? Research. Stop contacting people who don't need what you have.
Do they like you (and you them)? Genuine connection, not fake. Are they rude to the waiter? Drop them. You won't build anything sustainable with the wrong people.
Close the deal. If steps 1 and 2 are done, step 3 nearly closes itself. Simon has had clients propose higher budgets unprompted.

The long game

Top 1% salespeople (Harvard study) don't quit after five follow-ups. They keep their dream-customer list forever. Simon contacted his 50 dream customers every single month — some took 9 years to close. Not always with a pitch. A Christmas card, a relevant article, something useful. Politely persistent.

How to market

50% of what you spend on marketing is wasted. It's experimental. Three principles:

Understand your niche

Facebook started in universities and built the "single / in a relationship" feature — for exactly the right audience. When Sarah suddenly became single, the whole campus talked about it. The product did the marketing.

The staircase method

When a staircase came up for sale at auction in London, Simon bought it for £26,000. Two days later. No clear plan — but he knew a staircase symbolized step by step and that such an absurd story was newsjackable. Result: front page on BBC and the New York Times, millions in free PR. Then they put a doorbell on it — "have a dream? Press the button, we'll share it with our 4M followers." That became a follow-up story. Then a partnership with Ring/Amazon.

What's your staircase? What's the wild, unusual, newsjackable thing people will talk about?

Systems

One core piece of content → in-app edited for each platform. One video, five formats. Scale through systems, not by being on every platform badly.

PR

Target. UK BBC vs East Sussex Times — if you sell cherries locally, East Sussex Times is ten times more valuable.
Journalists are lazy. Write the press release as if it were the finished article. Strong headline. High-resolution images attached. Everything ready to copy-paste.
Skip agencies in early stages. Build a direct relationship with the journalist. Comment on their posts on Twitter/X — many journalists have small followings and read comments.
Be disciplined on your own social media. Brands say no to partnerships because of one bad post.

How to get an investor (or not)

Before you go looking for money — ask: do I really need an investor? Often the answer is no.

Ways to fund without classic VC:

Family & friends. Be brutally honest — "you might lose everything". Don't oversell.
Employees as investors. Think of the #2 at LinkedIn. They can't become #1 there, but maybe they want to build their own LinkedIn with you — and have money to invest. Win-win: lower salary, ownership, alignment.
Angel investors. Identify the right person. Ask for advice, not money. Create FOMO. Treat them with respect — they want to feel valuable, not like dragons in Dragons' Den.
VCs. Don't waste time with VCs that aren't actively deploying capital right now (Google them). Check their portfolio — have they already invested in your direct competitor? Then probably no. Get an intro through one of their portfolio companies.
Customers funding you. A Fluid client wanted them to open in the Middle East and paid for the expansion. Brilliant outcome — the client became invested in your success.
Crowdfunding. Pre-sell the product before you build it. Indiegogo. Equity crowdfunding. GoFundMe-style community support. No equity dilution.

How to get a sponsor

Two motives drive sponsors: measurable ROI and emotional connection. The sweet spot is both.

Understand the brand's values before you pitch. Simon lost a jewelry client by pitching beer-coaster ads.
Don't forget the people inside the brand. Their CEO or marketing lead has personal drivers — research them.
Shortcut: sell to the media buyers and agencies that already work with the brand. The brand is too busy — the media buyer holds the budget and the rolodex.
Use the brand in your everyday work. Simon chose Ring doorbell for his staircase because it was the best. Then Amazon saw the campaign and reached out.

How to build a brand

Value comes from brand, not business. Brands like Apple, Nike, Coca-Cola are worth more than their assets — because you know what they stand for without them telling you.

Two scaling models:

Reference model (e.g. Nike): you sponsor icons who represent your values. Risk: they do something bad and your brand takes the damage.
Leadership model (e.g. Apple under Jobs): one person is the brand. Risk: when they leave, the magic leaves (Apple post-Jobs has spent nearly a decade navigating that).

Learn to say no. The wrong client or partnership can destroy 30 years of brand-building in 5 seconds.

Personal brand

You will have a personal brand whether you want to or not — people talk about you when you're not in the room. The question is whether you design the story or let others.

Your personal brand can be that you're not on social media or don't reply to DMs. That's also a position. Define your rules.

How to hire, grow, and build

Hiring

Hire around purpose. Then you manage the purpose, not people.
Check their social media — do they say one thing and drive a gas-guzzling SUV?
Ask for references. Nobody does this anymore. Old-school but powerful.
Give equity. Loyalty isn't free. It's bought. Equal splits often beat 52/48 (the agreement governs decisions, not the ownership %).

The seven-and-eight rule

9-10s: keep them, give them equity, look after them
1-2s: everyone knows it isn't working — the problem solves itself
7-8s: the dangerous ones. You hope they'll become 9s, but they slip back to 6. They block the 9-10s from staying. You must learn to fire them — they're often grateful afterwards and find a role where they become 10s.

Test: are you talking about them more than once a week? Are you afraid of not finding a replacement? Then they're a 7-8.

Fire professionally

Help them find their next job. Simon has had former employees become friends after the firing, because the firing was straightforward and helpful.

Generalist → specialist

In the early stage, everyone does everything. To scale, you must build systems and shift from generalists to specialists. You included — Simon replaced himself as CEO of Fluid after 11 years with a better CEO.

Go global

Easier than it sounds. And it reduces risk — if one market tanks, you have others. Three paths:

Research. Where would your product work? Use it as a pitch point to investors and brand partners.
Franchising / licensing. Someone else does the work in the new market under your brand.
Brand partner funds the expansion (see funding section above).

It's easier to run a big company than a small one. Small locks you into doing everything yourself. Big has the means for senior management, which gives you the freedom you started for.

How to get a mentor (actually: don't bother)

People sell you the idea that you need a mentor. You don't. You need a coach, a co-founder, or just the answer to a specific question.

If you really want a mentor:

Research the person properly (Simon hates the property industry — don't ask him to mentor you on property)
Define what mentorship means — "10 minutes a week, these questions"
Reframe as advisor (board advisor) — more attractive, often equity, more structured
Get a referral — that's how yes becomes easy
Give value first. Simon always helps people who helped him first, unprompted.

Philosophy: give without take. Not give-and-take. People in pre-historic 5,000-person tribes gave without expecting anything back. They became the most respected.

Equity — what makes or breaks your company

Two misconceptions that kill businesses:

Ownership ≠ control. The shareholder agreement governs control. You can have 30% and still steer. Stop being scared of dropping below 50%.
Don't rush to give away equity early. The wrong investor on your cap table closes doors with later investors. Brand-align your owners.

Advice:

Co-founder: do 50/50. 52/48 psychologically belittles the partner. Use an advisory board for deadlock decisions.
Employees get real equity, not just share options. The difference is huge at exit or if the company gets delisted.
Use SAFE structures (Y Combinator style) to skip valuing the company early — the investor gets a discount on the future round.
Reverse-engineer the equity structure from your end goal. Plan to IPO? Today's structure must enable a future listing.

How to sell your company

The paradox: the best way to sell your company is to not want to sell it. It's the strongest negotiating position you'll ever be in. Mark Zuckerberg said no to Yahoo's billion-dollar offer. The company is worth a trillion today.

Paths:

Partnership. Simon sold Fluid to PwC after working together on a project. The acquisition grew out of the partnership.
Brokers/agents. Faster but be careful — do due diligence on them.
Competitor merger. Easiest, but often lower valuation. Selling outside the industry (creative agency → accounting firm) can pay more.
Management buyout. Let the team buy it over time. Rewards the people who built it with you.

Never build a company to sell it. You'll get stuck in a business you don't love. Build a company you never want to sell — those are the ones investors want to invest in and acquirers want to buy.

Closing

Simon says it himself: the school system doesn't want you to be free. Much of what you've read here runs against the grain — because it has to. Freedom, purpose, control of your destination, a business you love. It starts with asking what you love doing and what problem you want to solve, and ends with a brand and a culture that lives on even after you're gone.

Distilled from Simon Squibb's open 45-minute masterclass on how to start, build, maintain and sell a company — based on 30 years as an entrepreneur and investor.