LU 379: How Andrew Wilkinson of Tiny Capital Created a Portfolio of Companies Doing >$100M A Year On His Own Terms (podcast)

On today’s show, we are happy to welcome someone we’ve wanted to have on for some time now, Andrew Wilkinson. He is currently a Managing Partner at Tiny Capital, as well as the Founder of MetaLab, which helped design Slack. Along with this, Andrew is also invested in a range of other companies. In this episode, we learn more about his incredible journey and how he grew a passion for tech and design into a range of flourishing businesses. Andrew also sheds light on his investing education and overcoming his initial reluctance to see the power of investments. For Andrew, being an entrepreneur is about freedom to create the life you want, and having time to pursue your interests, which is how he saw the value of delegating. This is not easy when you are starting out your entrepreneurial journey, as Andrew knows, but as a company scales, so too should the owner’s levels of delegation. We take a look at the types of businesses Tiny Capital is interested in and why they are only pursuing simple business models. Our conversation then takes a turn into a different interest of Andrew’s — subscription podcasts. We discuss why these are such effective, yet untapped income-generating models and Andrew shares some of the work they are doing in this space. We then circle back to Tiny and leadership more generally where Andrew unpacks the importance of incentives along with his characteristic lazy leadership style. Andrew’s self-reflexivity and ability to talk openly about his weaknesses is truly refreshing. This conversation was a great look into what it really means to be an entrepreneur. Be sure to tune in today!

TIME-STAMPED SHOW NOTES:

• [00:21] Before we jump into today’s interview, please rate, review, and subscribe to the Leveling Up Podcast!
• [01:16] Hear more about Andrew’s background and his varied business journey so far.
• [06:58] What led Andrew to learn about investing and what stood out to him in his education.
• [09:39] Why Andrew is not a good CEO and what he has done to compensate for this.
• [10:41] Learn about a launchpad business and the opportunities it provides owners.
• [11:04] A common mistake entrepreneurs make: Building the first business to be venture-backed.
• [12:50] What Andrew’s day-to-day looks like and the different activities he’s involved in.
• [14:09] The kinds of businesses that Tiny Capital is currently interested in.
• [16:05] How Tiny buys businesses and some of the terms they stipulate.
• [17:01] Insights on how Tiny brings companies down from unrealistic venture valuations.
• [18:05] Tiny’s organizational structure and tips for anyone looking to start something similar.
• [20:58] Some of the characteristics that Andrew looks for when hiring a CEO.
• [21:48] Why hiring great executives when starting out is so difficult.
• [22:26] The different comp structures that are appropriate for these high-level executives.
• [23:13] How Tiny interprets profitability and different ways to manage cashflow.
• [24:18] The difficulties Tiny’s staff faced working on the range of entities and splitting attention.
• [26:10] Find out about subscription podcasts and why Andrew is so passionate about them.
• [31:09] Andrew’s interest in the No Code movement and why it’s valuable for business owners.
• [35:02] The motivation behind Tiny’s Twitter ads and their efficacy in relation to deal flow.
• [36:55] Andrew’s take on incentivization, common mistakes, and examples of good ones. [40:53] Incentive-related resources that have helped Andrew.
• [41:47] How Tiny thinks about company culture after founders have departed.
• [44:29] What it means to be a ‘lazy leader,’ and the role a CEO should play.
• [46:28] Books that have shaped Andrew as an investor.
• [48:11] Andrew’s favorite tool that’s not part of his portfolio.

Resources From The Interview:

• Tiny Capital
• MetaLab
• Andrew Wilkinson on Twitter
• Andrew Wilkinson on LinkedIn
• Dribbble
• Designer News
• Slack
• WeWork
• Steve Jobs
• TechCrunch
• Coinbase
• Shopify
• Warren Buffet
• SpaceX
• Berkshire Hathaway
• Zack Onisko
• Creative Market
• Supercast
• Tim Ferriss
• Joe Rogan
• DoubleUp
• Squarespace
• Flytographer
• Lambda School
• Bubble
• Coda
• Zapier
• Anthony Casalena on LinkedIn
• Charles Munger
• The Psychology of Human Misjudgment
• My First Million
• Superhuman
• SaneBox
• Jason Fried
• Basecamp
• HEY
• Must read books: The Dhandho Investor, Tao of Charlie Munger, Buffett: The Making of an American Capitalist

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