On content creation, fundraising, and investing: a conversation with Harry Stebbings, founder of The Twenty Minute VC

Harry Stebbings, founder of The Twenty Minute VC

On Friday, May 29th, EVCA hosted a fireside chat with Harry Stebbings, founder of The Twenty Minute VC, the world’s largest independent venture capital podcast. He is also the founder of Stride VC, a seed stage fund based in the UK. Harry shared the founding story behind Twenty Minute VC and Stride and his advice on content creation, starting funds, and investing.

Harry was first exposed to the world of investing through his father through helping him in his public markets work. He grew to love finance but turned to venture capital specifically after watching the Social Network. In the iconic scene where Peter Thiel invested in Facebook, Harry realized that venture capital was an incredible way to blend product and finance together.

Shortly after, he started listening to podcasts while walking and exercising, but realized that most podcasts featured the same few investors. He felt there was an incredible opportunity in interviewing and sharing the insights of the many other talented investors. He also dove deeper into the attachment of time and productivity gain and did consumer research on podcasting listening behaviors. He found that 82% of people do not return to a podcast again if they do not finish it the first time around, and most people listen to podcasts on commutes or on the go. With this framework, he created Twenty Minute VC, a way for people to learn from diverse investors in a short, efficient defined amount of time. He used $40 of the $50 in his bank account to purchase a microphone and other supplies to get Twenty Minute VC started.

To get his first few guests, he relied in part on referrals from existing guests, asking every interviewee to refer 3 others and make these introductions. The show steadily grew, and when it reached 1 million downloads in a month, Harry quit law school to work on it full time.

On creating content, Harry shares the following advice:

Specialize. Nowadays, there are so many people creating all kinds of content, so you must differentiate yourself by being the go to content source on a particular vertical or stage. Ultimately, you need to be able to point to something concrete that separates you.

Choose the medium that is best for you. Harry prefers verbal conversations to writing, so podcasting was a natural fit.

Bake distribution into whatever you do. Twenty Minute VC always asks investors on the show what their most recent publicly announced investment was. In this way, they incentivize the founders and teams behind the startup to also share the podcast. Similarly, sometimes companies that the investor sits on the board of will also share their podcast features. In general, it is crucial to think about how you can leverage people beyond just the interviewees to be brand ambassadors of your content.

On starting a fund, Harry highlights the following advice:

Make sure you want to be a founder. Working at a fund is incredibly different from starting your own fund. Expect to work like a founder for 3–5 years.

Find a complimentary partner. In the case of Stride VC, Harry needed a track record, which his partner, Fred (previously a GP at Accel) had. Fred needed a unique angle to differentiate himself from other GPs raising funds, which Harry provided with his media platform. Beyond the LP facing branding, the complimentary partnership has also helped them attract a wide range of promising founders. Younger founders gravitate towards Harry while serial entrepreneurs gravitate toward Fred.

Have a differentiated mission and approach. Harry and Fred truly saw a whitespace in the VC world, where they wanted to build a more founder friendly fund. For example, they aim for greater transparency and faster turnaround times when speaking with founders, and they only use whiteboards and not decks for founder diligence. In investor updates, they encourage founders to incorporate the upside thinking, underscoring how big their business could be with all barriers removed, which creates a fun exercise for founders and useful, inspiring data points for LPs as well.

Communicate a focus. LPs like to put funds into buckets, so make this process easier for them by clearly defining your focus in stage and geography.

Keep LP prospects updated on your fundraise. As new checks come in and the fund comes together, keep LP prospects in the loop (much like what founders do with VC investors). This can help inspire their confidence and bring you closer to closing them.

On investing, Harry notes the following advice:

Be mentally plastic. Being thesis driven can sometimes lead to an echo chamber where you only see what you want to see or only see through a specific, predefined framework. Follow founders, and they will lead you to the next opportunities.

Do a little each day, and it adds up over time. For example, Harry adds at least 1 company each day to his pipeline, which over time, quickly leads to a great top of funnel.

Conduct portfolio support through partnerships. Many times funds have a separate head of platform or platform team, but unless you truly go all in on platform support, it is usually more effective to support portfolio companies through partnerships with different service providers, advisors, and other resources in the ecosystem who each have their specific comparative advantage.

Understand the fabric of founders. Get to know them and what drives them and what challenges and formative experiences have shaped who they are. Ultimately, these are instrumental determinants of company outcomes.

On what he is excited for next at Stride, Harry is looking forward to creating greater liquidity for founders through secondaries, launching a US fund, and starting a fund of funds.

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