logo
episode-header-image
May 2018
32m 39s

20VC: Andy McLoughlin on The Benefits of...

Harry Stebbings
About this episode

Andy McLoughlin is Partner @ Uncork Capital, formerly SoftTech and one of the leading early-stage funds on the West Coast. In their incredible portfolio, they have the likes of Fitbit, SendGrid, PostMates, Front, PoshMark, Eventbrite and many more. As for Andy, he loves to invest in "unsexy ideas" with stellar teams and has led deals in the likes of Postmates, LaunchDarkly, Human Interest (previously Captain 401), and Focal Systems just to name a few. Prior to VC, Andy co-founded Huddle, an enterprise collaboration platform which raised more than $80M in venture funding before its acquisition in 2017. Andy also has a stellar angel portfolio with the likes of Buffer, Intercom and Pipedrive all angel investments.

In Today’s Episode You Will Learn:

1.) How Andy made the transition from Founder of one of the UK's hottest startups to one of the leading early-stage VCs in Silicon Valley?

2.) Why did Softtech decide to make the big decision to rebrand to Uncork several years into the journey? What is core to successfully relaunching a VC brand to the ecosystem?

3.) Andy likes to back "non-obvious founders" building "non-sexy businesses". What does Andy mean by "non-obvious founder"? How do they tend to behave differently to more seasoned serial entrepreneur founders from the valley? What does a "non-sexy business look like to Andy"? Why does he see such inherent opportunity within these segments?

4.) How does Andy evaluate the challenge of immensely long sales cycles within these industries? How can these be mitigated and measured against? How does this affect Andy's thinking on the right amount of runway to raise for? How does Andy assess the often issue of regulation? How does Andy distinguish between viable/ non-viable?

5.) How does Andy assess VC value add? Where does Andy believe he can provide the most value to his portfolio? Why does Andy believe startups are not just competing against other plays in their space but every startup in the valley?

Items Mentioned In Today’s Show:

Andy’s Fave Book: Venture Deals

Andy’s Most Recent Investment: Fritz

As always you can follow HarryThe Twenty Minute VC and Andy on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

We also speak about Movidiam – as brands turn to smarter ways of creating video and digital content, the Movidiam platform offers faster turnarounds whilst maintaining or improving quality. They’re already working with some of the biggest, most innovative companies to help compare teams and freelancers across the global curated network of creative talent. Producers and marketers looking for the best creatives can get a shortlist from Movidiam’s account managers in hours – tailored to their project’s needs. Submit a brief or check out the platform at Movidiam.com.

Up next
Yesterday
20Growth: The Death of Growth Teams? | How Hubspot Use AI to Triple Email Conversion | The Future of AI SEO | Why Prompt Engineering is the New Coding | What Every CMO Needs to Know About AI in 2025
Kieran Flanagan is the CMO at HubSpot, where he’s led the transformation of their growth strategy from SEO-led to multi-channel and AI-powered. Formerly SVP of Marketing, he helped scale HubSpot’s user base to millions and revenue past $2B. Before HubSpot, he drove breakout growt ... Show More
1h 15m
Jul 10
20VC: Daniel Gross and Nat Friedman: Acquired by Meta | OpenAI’s SBC Bombshell: More Stock Comp Than Revenue | Privat Equity is Back: Olo Bought for $2BN | Microsoft Lays Off 9,000 People: Is This Just the Start | Will Sequoia Part with Shaun Maguire
Agenda: [00:00] The AI Talent Crisis No One’s Ready For [03:00] Daniel Gross and Nat Friedman: Why Two Legendary VCs Walked Away From $1B to Join Meta [12:00] Meta’s AI Talent Magnet: Will It Actually Work? [15:00] Cursor Is Breaking the Market: Can Anyone Compete? [18:30] OpenAI ... Show More
1h 7m
Jul 7
20VC: Scott Galloway on Are Billionaires Happy & The Impact of Money on Psychology and Self-Worth | Becoming a Better Father & Husband | Why We Should Drink More and Not Work From Home | The Tinder Effect & How it Makes Young Men Radical
Scott Galloway is a Professor of Marketing at NYU Stern, where he’s taught for over two decades. He’s the founder of several successful companies, including L2 (acquired by Gartner for over $150M), Red Envelope, and Prophet. He’s a New York Times bestselling author of four books ... Show More
1h 10m
Recommended Episodes
Feb 2018
Andrew Tobias - “There Are Just A Few Things You Really Need to Know About Investing, and They Don't Ever Change" | #92
In Episode 92, we welcome investor, author, and activist, Andrew Tobias. Meb starts by asking Andy about his background and introduction to investing. Andy gives us his origin story, with highlights including collecting stamps, an early introduction to the stock market, a trip be ... Show More
53m 37s
Feb 2022
Joey Levin - Building an Anti-Conglomerate - [Invest Like the Best, EP. 264]
My guest today is IAC’s CEO, Joey Levin. IAC is a unique business in that it’s a holding company which builds world-class digital businesses. Since Barry Diller created IAC over two decades ago, it has produced 11 public companies, including Match Group, Expedia, and Live Nation. ... Show More
1h 10m
Mar 2022
Improving Market, Attractive Stocks
The S&P 500 rose for the 2nd week in a row, giving investors more reasons for optimism. Are we the only ones who believe the narrative for investors is shifting away from fear and towards increasing confidence? (0:45) Jason Moser and Andy Cross discuss investor sentiment, as well ... Show More
39m 30s
Oct 2022
How Elevate Labs Hit Cash Flow Positive in 2022 — Andrew Maguire, Elevate Labs
On the podcast we talk with Andrew about the journey to cash flow positive for Elevate Labs, the importance of creative, and why spending less money can sometimes be the key to figuring out paid user acquisition.Top Takeaways 📈 The journey to cash flow positive is a long one, de ... Show More
53m 47s
Feb 2023
Dan Rose - How Stunning Founders Operate - [Invest Like the Best, EP.316]
My guest today is Dan Rose. Dan is the chairman of Coatue Ventures and has one of the most interesting collections of experiences of anyone I’ve talked to. He spent 20 years at Amazon and Facebook in their early days, working closely with Jeff Bezos, Andy Jassy, Mark Zuckerberg, ... Show More
1h 13m
Mar 2021
How To Build A Massive Network and Brand Online | Dan Fleyshman | Replay
In this episode of the Millionaire Mindcast, Dan Fleyshman shares his secret sauce to success, and tips on how to be on top of your competitors, how to create a massive brand online, and how to balance your business portfolio! Dan Fleyshman is the youngest founder of a publicly t ... Show More
54m 22s
Feb 2021
Scott Belsky - Focus on the First Mile – [Invest Like the Best, EP. 213]
My guest today is Scott Belsky. Scott was the co-founder and CEO of Behance, the world's largest creative network, and a prolific angel investor, having made early-stage investments in Pinterest, Uber, Carta, and Airtable. His company was acquired by Adobe in 2012, where he is cu ... Show More
55m 31s
May 2023
Lessons From Over 100 Business Founded | Jeremy Delk
In this episode of the Millionaire Mindcast, we have our guest Jeremy Delk who shares his entrepreneurship journey for over 20 years of investing, successful exits, and logistics failure, the framework of a Fouder-type mentality, his learning lessons from founding over 100 busine ... Show More
48m 48s
Jul 2021
Angel Investor Is Turning 100 Entrepreneurs Into Business Millionaires | Mark Haney | FFT | Replay
In this episode of the Millionaire Mindcast, we have a humble and amazing guy, Mark Haney who shares his entrepreneurial adventure from managing video companies to a huge security company, how he has helped lots of entrepreneurs, talks about Angel Investing, and gives tips on how ... Show More
53m 21s