10 Lessons From a Founder Fighting Back in 2025

It’s that time of year when I’m reminding myself of the lessons learned and battle scars made over the last twelve months and reflecting on how they can help me launch into 2025 with a renewed sense of focus, grit and determination. So in the spirit of being transparent, I wanted to share them here in case they resonate with you and help you win the year.

Looking back at 20+yrs in the entrepreneurial ecosystem, I’ve founded and grown four businesses into seven-figure businesses, served on several boards, hired over a thousand leaders into every possible type of startup you could imagine, and picked up more than a few scars along the way.?

And if we’re being honest, 2024 was especially brutal - not just for me, but for so many founders. So for me, it’s more important than ever to make sure I’m recycling some of this learning and wisdom as I don’t want you making the same mistakes I did ;-)

So here are a few lessons I’ve learned, shared to help my fellow founders and leaders:

Fail fast but recover faster!

It might be an overused cliché but it’s a classic for a reason. Failure is inevitable. The key is not just failing fast, but recovering fast. Earlier this year, I faced a setback. While I failed quickly, I let it linger longer than it deserved. The lesson? Fail fast, and then get over it faster. Obsessing over the past doesn’t serve the future.?

Practice building resilience

Resilience is a muscle - the more you work on it, the stronger it gets. It’s more important than ever to build resilience in your business. Having weathered so many recessions and downturns, I’ve learned to see them not as insurmountable obstacles but as opportunities to adapt. Resilience equips you with the know-how when the chips are down: what to do when retainers dry up, how to handle pressure, and the tools to steady yourself when things feel out of control.

Build long-term partnerships

Generosity is a powerful strategy. I’ve always believed in offering advice and making connections without expecting immediate returns. Over time, this builds trust and goodwill, and strong networks can become lifelines, especially during tough times. Relationships compound, so nurture them.

Eat the goddamn frog!

We all dread and procrastinate on those difficult tasks. So do them first, and eat your frog in the morning. It’s astonishing how quickly you can defeat the mental monster that task has become - usually in 20 minutes or less. It unlocks something in your brain and the rest of the day will feel so simple.

Get comfortable being uncomfortable

Growth happens outside of your comfort zone. Last year, I really pushed myself - stepping onto stages, speaking at events, and facing moments of vulnerability. It’s uncomfortable, yes, but it’s also transformational.

Learn by doing not just reading

Everyone learns differently but I have found that theory can only take you so far. How do you become an angel investor without formal training? Jump in. Yes, I’ve made mistakes, some costly, but every lesson has been earned and paid forward. I’ve learned on the job and now I’m bloody good at it. Just remember: hands-on experience is invaluable, even if it feels messy in the moment.?

Make that decision

Decision fatigue is real. Our brain is only capable of making 35,000 decisions every day, so moving forward becomes a matter of necessity. Even imperfect decisions propel you further than indecision; you can always pivot and unpick later. Sometimes, even choosing to not make a decision is a decision in itself.

Obsess about the details

Details really do matter. Whether it’s clarifying expectations with a client, obsessing over contractual smallprint, or adding that extra touch, small moments of care will hold you in good stead and go a long way in building trust and loyalty. Thinking about the customer’s experience in detail is what keeps them coming back - and recommending you.

Don’t be afraid to defy convention

It’s easy to feel tethered to the ‘normal’ way of setting up a business, but breaking from the crowd will set you apart. At JD&Co, we’re built differently - no sales team, no marketing spend, and the confidence to trust in what works for us. We’ve also embraced tech and digital tools to work smarter, exploring AI tools that sharpen our speed and accuracy. Combined with years of human-learned experience, this approach has been transformational for client collaboration. Success often follows when you’re unafraid to rewrite the rules.

Build the right team

I would say that…but the success of any early-stage business hinges on the people behind it. After two decades of hiring for startups and scaleups, I’ve learned it’s not just about hiring skills and experience - it’s about passion, attitude, and a shared vision. Trust and belief in your team are essential for navigating what can be a bumpy, unpredictable journey. Don’t shy away from tough calls either; if someone isn’t meeting expectations or is creating friction, be decisive.

Let me know what lessons you learned last year in the comments and what you are going to do to win the year, love to hear?

Now go get ‘em!?

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