The guy with the mic had a point 🎤

How to start over, on your own terms

Apr 23, 2025

Simon Squibb is the bloke with the microphone asking strangers one question: “What’s your dream?” If you’re on TikTok, you’ve probably seen him. The clips made him famous, but I wanted to know what came before them.

Simon was homeless at 15, later built the Hong Kong creative agency Fluid and sold it to PwC. He also built Nest before selling that business through a management buyout. That history is why I picked up What’s Your Dream? in 2025.

I expected some familiar startup advice, and there is plenty in the book. The parts that stayed with me came from what Simon had actually lived through: starting with very little, selling a business and having to build again afterwards.

Some of his advice is basic, but it gets much more interesting once you know what happened behind it. These are the lessons I kept. 👇🏻

What’s your dream? Simon Squibb turned this line into a movement. *Illustration: ImageFX/MM*

How Simon Squibb made his money

Simon made his money by building and selling businesses.

Fluid, the Hong Kong creative agency he built, was acquired by PwC after years of growing the business and building the relationship that eventually led to the deal. He later sold Nest through a management buyout.

The exits matter here because Simon doesn’t write about selling as the neat finish line founders sometimes imagine. He talks about what came afterwards too, including the work of building his team and freedom again.

That experience gives some of the advice in What’s Your Dream? more weight than the standard version of “build something and sell it”.

Simon Squibb’s startup playbook

1️⃣ Ditch the success myths

Society loves to tell us what “success” requires: long hours, zero mistakes, and playing it safe. Simon calls nonsense on all that. Myths like “never fail” or “work till you drop” will kill your dream if you believe them.

He learned young that following others’ rules (school, corporate ladder) doesn’t guarantee anything. The lesson: question those so-called rules. Unlearn the junk notions that hold you back, so you can forge your own path.

2️⃣ Purpose powers the dream

“What’s your why?” might sound like a cliché, but Simon shows it’s serious fuel. When you marry a dream with a clear purpose, it can change your life. After crawling out of homelessness, his own drive came from a mission bigger than just making money.

One tip he offers: keep trying different ways of helping people until one gives you a warm glow inside. That warm feeling is a sign you’ve found a real purpose. Founders who anchor their startup to a mission (not just a product) have the fire to push through the tough times.

3️⃣ Ask the big three

Stuck figuring out what your dream even is? Simon suggests asking yourself three key questions: What do you love to do? What pain have you lived through? And how can you help others? The sweet spot for a meaningful venture is where those answers overlap.

For example, he tells the story of an entrepreneur who couldn’t find comfortable jeans after a medical ordeal, so she started a denim brand to help patients like her. Your own dream is probably hiding in your hobbies, your hardships, or the problems you can solve for others.

4️⃣ Don’t let money cage you

A fat salary or big mortgage can become a trap that kills your ambition. If you’re selling all your time to pay bills, you’ve built yourself a cage. Simon argues a possession should never be your dream. In other words, don’t chase stuff that locks you into a grind you hate.

Instead, aim for financial freedom. Live lean, cut the fluff from your expenses, and build assets or a business that doesn’t require trading hours for dollars. The less you’re enslaved by bills, the freer you are to pursue your real vision.

5️⃣ Master your mindset

If you don’t get your head straight, you’re done before you start. Simon treats failure as painful but priceless tuition for success. Instead of avoiding hard or scary tasks, he attacks them and suggests you do the same.

Every setback is just another lesson. This growth mindset builds the resilience every entrepreneur needs to survive the punches. You have to believe you can learn and adapt, or you’ll crack at the first real test. Train your brain to see opportunity where others see defeat.

6️⃣ Prepare, then pounce

Chasing a dream isn’t about quitting your day job tomorrow with zero plan. Simon uses a “build a boat” analogy: do your prep before you set sail. Gain skills, save some cash, make contacts. In short, set yourself up so you won’t sink the minute you leap.

But once you’ve built that boat, you do have to jump. One founder he mentions offered her services for free at a big event just to get her foot in the door; it worked because she was ready. The takeaway: preparation is power, but eventually you must act.

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7️⃣ Start lean, stay scrappy

When it comes to funding, less can be more. Starting a business with limited cash forces you to focus and get creative. Simon learned this the hard way after one of his ventures burned through a pile of investor money for nothing.

Now he preaches the upside of constraints. Be frugal, prioritise essentials, and make profitability a priority from day one. By building on real revenue (not hype), you create a business that can weather the storms. Remember, scrappy beats flashy.

8️⃣ Build your dream team

No great business is built alone, and Simon makes that clear. Your success will hinge on the people you bring along. He hires and partners based on values and passion, not just CVs. (In fact, he gives job candidates a “Madoff test,” an ethics scenario to see if they’ll put integrity over profit.)

The lesson: surround yourself with believers and doers who share your mission. The right team will propel your dream forward; the wrong people will sink it fast.

9️⃣ Flex your risk muscle

Playing it safe never built anything great. Simon urges founders to systematically push beyond their comfort zone. He even bent the rules with a guerrilla marketing stunt for one startup, a calculated risk that scored huge publicity.

The point: risk is part of the game. Take small bets often to build your risk tolerance, like exercising a muscle. Whether it’s launching a bold campaign or pursuing an unconventional idea, you won’t break new ground without taking chances. The more you risk (smartly), the more you stand to gain.

🔟 Never stop, no matter what

The only sure way to fail is to quit. Simon doesn’t mince words: persistence is everything. He highlights how even giants like Nvidia nearly went bust before they became industry leaders. They survived only because they refused to give up.

Every founder hits walls, from product flops to personal crises. Simon’s advice: treat setbacks as steps, not stop signs. If you truly believe in your dream, you owe it that level of grit. Keep moving, adjust the plan, but don’t ever give up on the goal.

1️⃣1️⃣ What selling Fluid taught him

Simon Squibb sold Fluid, the Hong Kong agency he built, to PwC after years of growing the business and building the relationship behind the deal. He later sold Nest through a management buyout.

The part I found more useful was what happened afterwards. Squibb says selling left him rebuilding for years before he had the team and freedom he’d previously created.

His advice is to build a business somebody would want to buy without making the sale itself the goal. Step away from the day-to-day as the business grows. If an offer arrives, you’re then deciding whether you actually want to sell rather than discovering that the whole business still depends on you.

That’s a much more useful way to think about an exit. The cheque matters, but so does what you’re giving up to get it.

💡 How to start over, on your own terms

Simon’s advice in What’s Your Dream? is hard, some of it is messy, but all of it comes from someone who’s actually built, sold, and started again.

You don’t have to nod along to every line. But there’s something grounding in Simon’s core message: you don’t need to have it all figured out before you start. You just need conviction, scrappiness, and the guts to ask for help early.

If you’re building something, especially without a safety net, this book won’t tell you what to do. It’ll remind you why you started. And maybe that’s what you need most.

You’re allowed to dream and to make it up as you go. Just don’t sit still.