Founder advice has become locked in an echo chamber. Much of it is repeated by people who say what they think they should, rather than what reflects their true experience.
After 25 years and several companies, here are four things I wish someone had told me earlier in my entrepreneurial journey. I still rarely hear them said out loud, but they continue to guide me today.
1. ‘Never give up’ might be the worst advice you can get
There is a certain caricature of the founder who refuses to quit, no matter what. I drank that Kool-Aid for years, and it cost me. The truth is far more nuanced.
Knowing when to change course is one of the most valuable skills an entrepreneur can develop, and it’s an art, not a science.
Pivot too soon and you create a self-fulfilling prophecy: it didn’t work because you didn’t try hard enough.
Hold on too long and persistence can become your Achilles heel, even fatal at times.
The most successful businesses and entrepreneurs I admire have been able to pivot and change direction when necessary, guided by honest assessment and sound judgement.
2. ‘Choose your investors carefully’ is unrealistic advice
You’ll hear this at nearly every founder event. The speaker on stage tells you they had 10 term sheets and chose the wisest partner.
The brutal reality? Most founders are not in that position. If you get one or two investors willing to back you, that is something to celebrate, not apologise for, and you should grab those opportunities with both hands.
So when someone tells you to be selective, and you’ve never had the luxury of choice, don’t feel small or think you’re failing. You’re doing what almost everyone else is doing. And remember, if it sounds too good to be true, it rarely is.
3. Cool company culture starts with outcomes, not a funky office
Read any story about a startup and you’ll see profiles of beautifully designed offices, beanbags and barista-quality De’Longhi coffee machines.
Meanwhile, you might be in a shared 20-desk space, or even smaller, wondering what you’re doing wrong.
Culture can’t be created with an office slide or a foosball table. A great company is built by delighting your customers. For us, that means patients, practitioners and partners, and watching that success show up in the numbers.
If your revenue is growing and you’re profitable, if your people care and bring their best selves to work, then you’re a cool company.
The rest is froth. A dedicated team, meaningful work, authenticity and people who are genuinely learning will matter far more than a “cool” office space.
4. Founding a company won’t buy you freedom
Recently, I heard someone on the radio describe entrepreneurship as becoming “captain of your calendar” and “director of your destiny”.
If that’s why you’re doing it, please don’t. I thought this myth had already been debunked, but clearly not.
So I’m here to do exactly that. The reality is that when you become a founder, the grind gets harder.
The flexibility is less. The responsibilities can feel impossible. There are weeks when every decision sits with you and every cost is yours alone.
A week in the life of Craig Brennan – from boardroom to touchline
None of this is a reason not to do it. Building something meaningful is one of the most worthwhile things a person can do with their working life.
But go in clear-eyed about what it really requires, not what the conference circuit claims it does.
The advice around entrepreneurship is loud, sometimes inauthentic and almost always delivered by people trying to impress.
It’s time we had quieter conversations grounded in reality, conversations that are reflective and honest.
To succeed as early-stage entrepreneurs, we need role models we can relate to, not people we simply aspire to become.
- Ranjan Singh is the award-winning CEO and co-founder of HealthHero, which he founded in 2019 and grew into Europe’s largest digital clinic, delivering care to 35 million people and conducting 4 million consultations annually. A serial entrepreneur, Singh has spent more than 25 years building, scaling and investing in digital businesses across travel, retail and healthcare.