Case Study: Supporting Founders Through Experience and Practical Insight

Venture Partner: John Cole

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Background and Experience

John’s career spans the military, startups and scale up businesses, giving him a unique perspective on resilience, leadership and decision making under pressure. His journey began in the Royal Navy, where he spent nearly eight years in operations and training. There, he developed the ability to think clearly under pressure and the importance of a strong team, lessons that have served him well in the fast paced world of entrepreneurship.

After leaving the forces, John transitioned into the startup ecosystem, where he has spent over twenty years founding, scaling and investing in companies. With two successful exits and a current role as a board member and investor at Ezoic, John has firsthand experience navigating the highs and lows of business growth.

Beyond formal roles, John takes pride in the fact that more than ten individuals he has hired and worked alongside have gone on to build successful companies, some securing venture capital and private equity funding. His experience spans fundraising, operational strategy and founder support, with a strong focus on helping entrepreneurs make informed decisions when it matters most.

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How John Works With Founders

John’s focus is on providing practical advice and guiding founders through key inflection points, particularly around fundraising, capital allocation and business exits. He believes that:

Clarity under pressure is critical. Founders often face overwhelming uncertainty and John's ability to simplify complex situations helps teams move forward with confidence.

Raising capital should be done sensibly. He advises founders on securing funding without overcommitting or diluting their long term vision.

Avoiding costly mistakes can be the difference between success and failure. He helps founders sidestep common pitfalls, particularly when scaling or preparing for an exit.

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Real Impact: A Founder’s Journey

One founder John worked with was facing a crucial decision on whether to accept a funding round with highly restrictive terms. The pressure to secure capital was immense, but John helped reframe the challenge, focusing on the long term implications rather than the immediate need.

Through strategic guidance and leveraging his network, John helped the founder secure an alternative investor with far better alignment. This enabled the company to scale without sacrificing control, ultimately leading to a successful acquisition two years later.Led recruitment efforts, identifying final candidates for the leadership team to interview.

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John’s Investment and Sector Focus

John’s angel investments have been targeted, focusing on IoT scale-ups and digital assets, but what matters most to him is backing great founders when they are gaining traction and making pivotal decisions. He is especially passionate about education, where strong execution can create a lasting impact.

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Why John Works With If Capital

At If Capital, John is committed to putting founders first. Running a business is, in his words, “the hardest game I know” and his goal is to step in with practical insights, a fresh perspective and a steady hand when it matters most.

For founders looking for an experienced partner who has navigated both the operational and investment sides of business, John brings deep expertise, a sharp analytical approach and a founder first mentality.

If you are scaling your business and need support navigating fundraising, exits or growth strategies, let’s have a conversation.