Business Athletes: Harry Ratcliff

Hello and welcome to Business Athletes everyone 👋 

Each week, we’ll explore the athlete-like habits behind a different business leader and provide you with practical tactics that you can quickly apply in your day-to-day.⚡️

This week in Business Athletes, I sat down Harry Ratcliff, co-founder of DealSage, an AI-powered acquisition toolkit built to streamline the process of buying businesses.

Designed for search funds, independent sponsors, and acquisition entrepreneurs, DealSage helps users evaluate opportunities faster, model deals more accurately, and automate time-consuming diligence.

Before launching DealSage, Harry worked in investment banking at JP Morgan. Today, he’s building a product for the fast-growing search fund and ETA (Entrepreneurship Through Acquisition) space, all while helping get four kids ready each morning alongside his wife. 

What stood out most in our conversation was how deeply intertwined his personal and professional life are. His wife isn’t just a life partner. She’s part of the rhythm that makes his days work. His co-founder is his brother-in-law and longtime friend. 

DealSage isn’t just a startup for Harry; it’s a reflection of the life he’s trying to build, one rooted in flexibility, family, and doing meaningful work with people he cares about. It’s designed for others on a similar path: people using business ownership not just to make a living, but to design a life.

This edition is a masterclass in ruthless prioritisation, calm execution, and self-awareness – from both a founder and a father.

Let’s get into it. ⚡️

Pre-Game Preparation

A Day In The Life

I’m a father of four, so before I even sit at my desk, I’ve already done a full shift.

My day starts at 6am when my son wakes up and enters the room like a human alarm clock. From then until 8:30am, it’s all about getting four kids ready – breakfast, dressing, routines, and out the door.

At 8:30am, I switch gears and start my workday. But the truth is, the day starts the night before.

Once the kids are asleep, I’m back at the desk around 7:30pm and usually work until 10 or 11pm. I use that time for deeper focus tasks like writing, marketing, and long-term planning. The house is quiet, the distractions are fewer, and I can think clearly.

Before bed, I always map out the next day. I make sure I have the key time blocks, major deliverables, and tasks that actually move the business forward mapped out for the following day. 

Deep Into The Game

Focus Is A Decision, Not A Condition

My principle around flow is to just get on with it. 

Maybe it comes from the investment banking days, where you get home and get a message from your MD and you need to edit a model or pitchbook wherever you are. You just have to be ready to perform at all times. 

Sure, I like a clean office, natural light, and binary beats (I can’t do lyrics when I’m deep in thought). But I’ve trained myself not to rely on any one setup. I don’t wait for the perfect conditions. I just perform.

Startup life is like sport: you won’t always get the warm-up you want. But you’ve still got to show up and deliver. That’s how I approach flow.

The Championship

The Real Win: Living On Your Terms

The long-term championship for me isn’t a finish line. It’s a lifestyle.

At first, I wanted freedom: time, location, independence. But over time, I’ve realised it’s not about arriving at some future state. It’s about living the life I want to live today. 

I want a worthwhile challenge and to build something meaningful. I want to do work that doesn’t feel like work. I want to be the kind of father who’s present, patient, and intentional. That’s why I connect so deeply with what we’re building at DealSage, because in many ways, we’re helping others do the same: design a life on their terms through business ownership.

DealSage is part of that championship. Building a business that powers the search fund ecosystem and becomes the go-to partner in this space. We’re chasing some big enterprise contracts, thinking deeply about integrations, and building momentum every day. But the biggest win is crafting days I actually want to live.

Lessons From The Field

Literal Up-Hill Battles Build Resilience

My approach to mental resilience is simple: don’t get flustered, and keep pedalling.

But nothing throws curveballs at you like parenting.  I’ve learned not to overreact. The way you respond often does more damage than the problem itself. I expect things to go wrong. I stay calm. And I move on.

Sure, investment banking helped build some resilience, but I actually get it from sports….

One of my most formative experiences was cycling from London to Rome. That was 26 days, 120km a day. We camped every night and had zero cycling experience before starting, and only took 1 day off the entire trip. 

At one point, we hit a 40km uphill stretch through the Alps. It was relentless. But you realise something: the only way is forward. You stop focusing on how steep it is, and you just keep turning the pedals.

It taught me something simple: you can always do more than you think.

That mentality shapes how I build DealSage - you just keep showing up, keep pedalling, and eventually the mountain gives way.

Leading By Example Begins At Home

Nothing has tested my leadership more than being a parent.

You don’t get performance reviews from toddlers - only instant feedback when things go wrong, and a long delay before you know if you’ve done anything right. But that’s the game. You show up, stay patient, and try to be consistent - even when it’s hard.

At home, our biggest battle is nutrition. We’ve cut alcohol, red meat, and sugary drinks. Not out of perfectionism, but because we believe health is foundational. And just like with a team, I don’t preach, I try to lead by example.

Want to explore DealSage? Click here to book a demo or sign up for free to check it out yourself. Enjoyed Harry’s insights? Connect with him on LinkedIn here for actionable takes on all things M&A, business acquisitions and being a parent.

The Business Athletes Mindset

What does being a Business Athlete mean to you?
Doing what needs to be done, when it needs to be done.

What does winning the day look like for you?
Being a present dad and staying calm with the kids. That’s the biggest priority.

Process or Outcome?
Process, but with eyes on the outcome. That faith in the day-to-day matters.

Mind or Body?
Mind, though I’ve been guilty of analysis-paralysis before. But I learned how and when to take action, and I have a partner that compliments me.

What one thing moves the needle the most as a founder?
Prioritisation. Everyone knows it’s  important, but living it is a completely different beast. So, it’s doing what’s important, not just what’s enjoyable.

Performance Stack

Here we cover the top 3 resources, tools and practices that drive high-performance and wellbeing for Harry:

📚 Favourite Books: 

1. Buy then Build, Walker Deibel - the book that got me on this search/eta path many years ago.

2. Skin in the Game, Nassim Nicholas Taleb - the book that made me feel like i was being called out and instead should want to add value to the world, not just be a middle man.

3. The Road, Cormac McCarthy - hits hard as a father.

🛠️ Tools You Live By:

1. Brain.fm app for binary beats - I use daily.

2. Blue light blocker glasses I wear every evening. I really feel the impact of them.

3. Notepad and pen. I still love the act of writing notes, thoughts and just scribbling.

🎯 Key Practices:

1. No phones when with the kids - not easy but my wife and i really put this into practice.

2. Get outside as much as possible, beach, walks, runs - every weekend we do something outside.

3. Reminder to speak to my parents every week. 

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