Shuttle's Q&A with Ian Madigan

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Now, let’s get into it 👇

Last week we recorded our first webinar with ex international rugby player, and Shuttle Investor, Ian Madigan. We had a great chat about Shuttle, where the idea came from, our journey until now and our plans for the future. We also answered some questions submitted by all of you, our community. The conversation was a lot of fun and we think you’ll enjoy watching, if you haven’t already. Watch the full stream above or see below for specific questions along with a summarised version of each answer. Enjoy!

“As regards the risk involved, people will obviously want to get a better understanding of that. Can they expect to double their money, to triple their money over a period of time? How do you guys look at managing risk?”

Venture capital is a long-term, illiquid asset class, typically locking investors into a 5–10 year horizon before returns materialize. Managing risk effectively in venture capital primarily involves extensive diversification. Investing in only 5–10 companies isn’t sufficient and significantly increases the chance of losing money. Instead, constructing a broad, geographically diverse portfolio—across the US, UK, and Europe—with at least 30–50 investments substantially reduces risk.

Statistically, a portfolio of around 50 investments lowers the probability of losing money to below 5%, approximately around 2.5%. Crucially, venture investing offers asymmetric returns, meaning the potential upside of successful investments is disproportionately large, potentially 20–50 times or even more. Typically, a few successful companies in a diversified portfolio significantly offset losses from underperforming investments. Our strategy at Shuttle emphasises broad diversification through quarterly investment drops, spreading capital across multiple opportunities consistently over several years, thus maximising potential returns while effectively managing risk.

“How should I think about allocating to start up investing as part of the broader portfolio that I might have or people listening would have?”

Venture capital shouldn’t be something you pour all your money into; it’s part of a broader investment strategy. Typically, the bedrock of most people’s portfolios consists of things like index funds and individual stock picks. The core principle is diversification, not just within an asset class but across multiple asset classes.

Public market investments are typically correlated to the economy, meaning when something happens, your whole portfolio tends to move together. Venture capital offers a way to add diversification, giving you a speculative edge with higher risk but also potentially much higher returns, while being less correlated to traditional assets.

We suggest allocating around 10% to 20% of your overall portfolio into venture capital or startups, depending on your personal circumstances and risk appetite. At Shuttle, we provide an indexed approach, giving you as many shots on target as possible, making it accessible and simple. Doing all the sourcing, screening, and due diligence yourself is difficult, costly, and time-consuming. Our goal is to reduce these barriers and make venture investing straightforward and broadly diversified.

“If Shuttle was to cease trading, what would happen with their investments?”

Everything is safeguarded. Shuttle uses a nominee structure to hold all investments separately from Shuttle’s business. Customer funds are managed through a regulated payment service provider, ensuring accounts with investable funds are completely segregated from Shuttle itself.

Shuttle could disappear tomorrow, but all customer investments remain protected, managed independently by the nominee. Shuttle maintains a strict separation between its business operations and client capital, meaning investors remain secure regardless of Shuttle’s business continuity.

“If people's individual circumstances change and they're unable or they decide to stop paying their annual membership fee, what would happen with their investments?”

If someone stops paying their annual membership fee, they’ll still have access to track their existing investments. They won’t see new investment opportunities, but they’ll retain a restricted view of their current portfolio and continue receiving company updates.

“Are there any tax incentives with investments like this?”

The answer is that it depends. There are tax schemes such as EIS in Ireland, or EIS and SEIS in the UK, where investors can potentially claim back up to 50% of their invested capital, making them very attractive. However, eligibility depends on whether the specific company is fundraising under these schemes.

At Shuttle, supporting these schemes will be on a case-by-case basis. Some of the best startups might not opt to raise under these schemes due to certain drawbacks or because they’re able to easily fill rounds without them. But if one of our portfolio companies does offer EIS, we’ll clearly communicate that opportunity to our investors.

“What makes you guys capable of picking these right opportunities?”

What sets us apart is that we only invest in deals where an institutional venture capitalist is already leading the round and setting the terms, which we then follow. In each of the four investments we’ve made so far, there have been at least three separate VCs involved, providing multiple layers of due diligence beyond our own.

This means our customers aren’t just relying on our judgment alone; they’re effectively investing alongside experienced institutional VCs with proven track records. This approach helps build trust and gives our customers additional comfort.

“What are the exit points along that journey where you can still get a return on your investment, but the company wouldn't necessarily have to go all the way to a public IPO?”

There are several possible exit strategies within venture investing. The best-known is the IPO, which is often the ultimate goal. More commonly, startups exit through mergers and acquisitions (M&A), where they’re bought by a larger competitor or incumbent. Increasingly popular are secondary sales, where companies allow early investors or employees to sell a portion of their shares during later fundraising rounds or via secondary trading platforms like EquityZen or Hiive.

What we’ve been working on at Shuttle

• Completed our Webinar with Ian Madigan 🎥 🔴

• We appeared on the Money Never Sleeps podcast here 🎙️

• More work on our AI integrations within WhatsApp 🤖

• Working on sourcing the opportunities for our next drop 🔎

• Working towards launching our first affiliate partnership very soon 🤝

The Unsophisticated Investor is brought to you by Scott & Rob, the founders of Shuttle. We’re both sick of private markets being a playground exclusive to the ultra-wealthy so we started a company to challenge the status-quo. Shuttle’s singular focus is to unlock private markets for Millennial and Gen Z tech professionals and help them build wealth through the highest performing private market opportunities.

Scott & Rob
Shuttle Co-Founders