BenSheppard

I’m a four-time founder with one exit, ventures launched across Hong Kong, Switzerland, Spain, and the UK, and millions raised from US and European investors. I’ve negotiated hundreds of millions in enterprise deals and led companies from idea to revenue across AI, infrastructure, SaaS, and deep tech.

I have advised founders through their own exits and a founder buyout in the last year. I learned that discipline a decade earlier in infrastructure, finance and M&A, including as buy-side advisor on a $67M acquisition. The mechanics do not change much with the number of zeros.

Today I work with founders and leadership teams at the moments that matter most: scaling, turnaround, and exit. I work on the business and the people running it at the same time, because when both evolve together the results are faster, stronger, and they last.

I have spent 22 years in business, twelve of them in startups, building and coaching across four continents, multiple sectors, and every stage from early concept to exit. That includes raising $2.2M pre-seed for my own company, navigating a full pivot under pressure, and reaching $1M ARR within twelve months of that pivot. I have also helped the founders I work with win grant funding and land the customers that decide whether they make it.

Before coaching and operating full-time, I spent a decade closing deals that most people never get near — infrastructure financing between governments and private institutions, transactions worth hundreds of millions, negotiations with multilaterals, development banks, and Fortune 500s. That world taught me how large institutions think, how they move, and how to get them to yes. It is why I am effective at enterprise B2B, why founders bring me into their biggest commercial conversations, and why I have been able to build a network of 30,000 across the industries that matter. I am not a strategist who advises from the sidelines. I am a deal maker who gets in the room and moves things forward.

The common thread across everything I have built and every client I have worked with is execution under pressure — and the judgement that comes from having done it yourself, repeatedly, across different contexts.

I am also a HYROX competitor. That is not a footnote — it is relevant. I am at my most effective when I am moving, not at a desk. My best thinking happens on a long walk or in the gym, not in a spreadsheet at midnight. Understanding that about myself changed how I work. It is also why Inside Startups is built around brain, body, and business as a single integrated system — because I learned the hard way that the human running the business is not a constant.