What I'd Do Differently If I Started a Business Tomorrow: Part 1

The brutally honest advice I wish I'd followed before spending years learning it the hard way.

After eleven years building companies and watching others succeed and fail, I'm often asked: "What would you do differently if you started again tomorrow?" My recent TikTok series on this topic generated more DMs than I expected—probably because I skipped the inspirational stuff and got straight to the point.

Here's the expanded, unfiltered version for those who wanted more details.

1. I'd Hire the People I Know Are Superstars

The greatest advantage of building a second business is the network of talent I've discovered along the way to date. Over the years I’ve had the privilege of working alongside so many incredible people – people with the right attitude - who would be my first call for the next venture.

To this day, I still think that any interview process is hit/miss. There’s no bulletproof way of weeding out the superstars from the rest, is there? But today, I know dozens of absolutely brilliant people who consistently deliver exceptional results.

These are people who:

• Have proven their capabilities under pressure

• Understand how startups actually work

• Are flexible to try new directions, new strategies

• Share my work ethic and values

• Can operate with minimal direction and maximum impact

• Are brilliant people to work with / elevate the team around them

The talent you surround yourself with is the ultimate competitive advantage. No business strategy, however brilliant, survives execution by the wrong team.

2. I'd Choose Brilliant Cofounders

Due to work and my social environment, I’m constantly around other entrepreneurs and business leaders, many who are utterly brilliant. I'd leverage my network to bring onboard 1 or 2 other entrepreneurs as my cofounders, people who have done it before and who bring some serious gravitas.

Solo founders face an uphill battle. The statistics are clearly in favour of cofounding teams: companies with 2-3 cofounders outperform solo ventures consistently. But having the wrong cofounders is worse than having none at all.

Next time, I would:

• Partner only with people who are supremely well-respected in their field

• Ensure completely complementary skill sets with minimal overlap

• Verify shared values about work ethic, quality, and vision

• Test compatibility through a small project before fully committing

• Establish clear ownership and decision-making frameworks from day one

The right cofounders multiply what's possible; the wrong ones create existential company drama that drains energy, resources, and motivation. No one has time for that.

3. I'd Be Strategic About the Industry

I'd deliberately position myself in an industry with clear investment appetite—something innovative, scalable and aligned with long-term global trends.

With Huckletree, I followed my interest without considering the broader market context. As it happens, I got lucky and this turned out well for me, but in the future, I’d be certain to choose an industry with structural advantages. Passion matters, but being selective about which of your passion to turn into a business is smart strategy, not selling out.

I would target sectors with:

• Growing market size (minimum 10% year-over-year)

• Limited but not absent competition (proving market demand exists)

• Alignment with macro trends (longevity, AI, demographic shifts)

• Potential for network effects or economies of scale

• Multiple exit opportunities

The playing field is never level. Some industries offer tailwinds that make success more likely; others present headwinds that make every achievement twice as difficult.

4. Fundraising Wouldn't Be My Goal

I'd build a sustainable business based on good foundations—a strong business model, great people and a clear vision. If fundraising is needed, it would be when the business is in a strong position (and on my terms).

Too many founders treat raising capital as a goal rather than a tool. Investment rounds are chased as validation, rather than focusing energy on building something worth investing in. This doesn’t make sense to me (and never has).

I would:

• Self-fund until the business model is proven (one of the benefits of a second business if that the cofounders are more likely to be in the position to invest some of their own capital)

• Define clear milestones that require outside capital

• Approach fundraising from a position of strength (eg. once the company is already revenue generative, thesis has been proven)

• Maintain enough runway to walk away from bad terms

• Be selective about investors who add genuine value beyond money

The best negotiating position is being able to say "no" and mean it. Building a business that can survive without external capital gives you that power.

5. My Focus Would Be Entirely On Profitability

I'd ensure profitability first and foremost. None of this "build for growth" crap. Those days are long gone. Cash is king. We've seen too many companies raise massive amounts of capital only to never reach profitability.

Some close to home examples:

Made.com, once the darling of British e-commerce, went from an IPO valuation of £775 million in June 2021 to bankruptcy just 16 months later. Despite raising over £137 million from leading European investors, their losses ballooned from £10.1 million to £35.3 million in the first half of 2022. All 500 employees lost their jobs, and thousands of customers never received their orders or refunds.

Infarm, the Berlin-based vertical farming company that raised $473 million to become Europe's most prominent indoor agriculture business. Founded in 2013, it achieved unicorn status with a billion-dollar valuation before collapsing spectacularly. By late 2022, Infarm was laying off more than half its workforce and by 2023, it had shut down operations across all its key European markets—UK, France, Germany, Denmark, and the Netherlands. The company filed for bankruptcy and had to sell off its assets through administrators.

In my next venture, I would:

• Target profitability from day one, not year five

• Build with minimal fixed costs and maximum flexibility

• Price products for actual profit, not market share

• Only scale after proving unit economics work

• Raise capital to accelerate success, not to experiment with business models

The businesses that survive aren't necessarily the fastest growing or most heavily funded; they're the ones that control their own destiny through positive unit economics and manageable cash flow.

The public market has made it clear they're unwelcoming to cash-burning companies. Many startups that raised mountains of capital during the lower interest days of 2020 and 2021 are now facing a harsh reality when they try to maintain their unsustainable valuations.

Profit isn't just a goal—it's feedback that your business model actually works. Growth without profitability is just supremely expensive hope.

The True Advantage of Experience

The difference between first-time and second-time founders isn't just knowledge—it's knowing where to focus. First-timers spread themselves thin across everything; experienced founders concentrate exclusively on what moves the needle, and hand the rest over to the team.

If I were starting again tomorrow, I'd ignore:

• Fancy titles and org charts

• Press coverage and industry awards

• Pitching at endless startup events

• Having the perfect logo, website, or brand identity early on

Instead, I'd obsess over:

• Finding and convincing the best people to join

• Building something people actually want to pay for

• Creating a culture that attracts talent through reputation

• Establishing systems that scale beyond my personal capacity

The Ultimate Lesson

After all these years building Huckletree, the most valuable insight I've gained is this: successful businesses aren't built on brilliant ideas or perfect execution. They're built by people who learn faster than their competition and adapt accordingly.

So while this list reflects a few of the things that I'd do differently, I'm under no illusion that I wouldn't make an entirely new set of errors. The difference is that I'd recognise them faster, pivot more efficiently and definitely waste less time on things that don't matter.

The question isn't whether you'll make mistakes—you will. The question is how quickly you'll learn from them.