Andrew Dumont: Adventures in Business and Investing

Andrew Dumont is the Founder of Curious Capital and CEO in Residence at Tiny Capital. He was previously the CMO of Bitly and an Entrepreneur in Residence at Betaworks. He’s spent his career building and growing companies like Moz, Seesmic (acquired by Hootsuite), Stride (acquired by Copper), and Tatango. He’s also an advisor at Techstars and Startup Weekend, and he writes for Inc. Magazine.

Andrew was named one of Forbes’ 30 Innovators Under 30 in Marketing and was appointed an entrepreneurial delegate by the United Nations. In this episode, Andrew and Daniel discuss scaling an open source framework, the business of job boards, the three steps for turning around any business, and Andrew’s approach to investing.

📻 Listen and subscribe now on Apple Podcasts, Spotify, Overcast, Breaker, Castbox, Google Podcasts, or on your favorite podcast platform.

“When you’re first starting a fund, you’re going to spend your first five years, realistically, actively raising money from LPs—and that is your primary role. It is not interfacing with founders and helping entrepreneurs; that’s a small piece. I think it’s important that people realize: if you just want to work with entrepreneurs all day, join an existing fund.” – Andrew Dumont

Chapters in this interview:

• 00:00:07 – Andrew’s start in the world of venture capital
• 00:06:38 – Why venture capital isn’t the best option for all startups
• 00:12:48 – Andrew’s work with Betaworks
• 00:18:41 – The truth about choosing companies to invest in
• 00:21:51 – Why companies succeed
• 00:24:52 – Andrew’s work with Tiny Capital
• 00:35:17 – Making an acquisition grow
• 00:40:19 – Getting started with investing 
• 00:43:46 – The realities of managing a fund
• 00:50:44 – How investors can best help founders
• 00:56:05 – Why getting reps as investor is exciting

For more explore the transcript of this episode.

Links from the Episode

• Connect with Andrew: Twitter | LinkedIn | Andrew’s Website
• ‍Curious Capital
• Tatango
• Seesmic
• Hootsuite
• Moz
• Bitly
• Betaworks
• Tiny Capital and co-founders Andrew Wilkinson and Chris Sparling
• Good to Great: Why Some Companies Make the Leap…And Others Don’t by Jim Collins
• Blokable
• Giphy
• Poncho
• Digg
• Notion
• Y Combinator
• We Work Remotely 
• ZipRecruiter
• Indeed
• Meteor
• JavaScript
• Kevin O’Leary of Shark Tank

How do you inherit an existing business and make it become more successful?

• Step 1: Make it more efficient. Find inefficiencies in cost (software, hosting, contractors, outside resources), and get the business in better financial condition from day one.
• Step 2: Find the quick wins that will immediately change the trajectory of the business. Look at business models, customer communication, marketing motion, etc.
• Step 3: Figure out the team you need to really make the company compelling. Find people who can drive the business forward with their passion and skills.

Considerations before starting your own fund 

Remember that you will not spend your time talking to entrepreneurs and helping them with their work. Your primary role will be to raise money, and your first five years will mostly be spent actively raising money from LPs. If you really want to work with entrepreneurs all day, join an existing fund.

On Outliers, Daniel Scrivner explores the tactics, routines, and habits of world-class performers working at the edge—in business, investing, entertainment, and more. In each episode, he decodes what they’ve mastered and what they’ve learned along the way. Start learning from the world’s best today. 

Explore all episodes of Outliers, be the first to hear about new episodes, and subscribe on your favorite podcast platform.