077: Bootstrapping vs. Raising Money with Chris & Rob Taylor

Today, I’m speaking with the powerhouse brother duo, Chris and Rob Taylor. Here’s a bit of context… Chris founded a company called Square Root in 2006 which helps automotive OEM field managers understand and act on unique data patterns and opportunities for retailers in their markets. The company was acquired by CDK Global, where Chris continues his journey as Vice President and General Manager. His brother Rob Taylor is co-founder of Austin-based Convey, which was acquired for $255 million by project44. Convey powers direct-to-consumer delivery experiences for more than 2,000 of the world’s largest brands. What’s interesting is that Chris & Rob took very different startup paths, but got to very similar destinations. Chris bootstrapped and scaled a single startup over the course of 17 years and didn’t take a single dollar of outside money. Rob on the other hand, leveraged venture capital to fund 7 different startups over a 20 year period. It’s a go big, go fast strategy. Both paths have pros and cons that we dig into during today’s conversation. These guys have had major exits, and major success, and I wanted to talk to them all about their experience building, scaling, and selling businesses.  We discuss entrepreneurship, acquisition deals, IPOs, bootstrapping vs. raising money, VC partnerships, and so much more.   Want the Full Show Notes? To get access to the full show notes, including audio, transcripts, and links to all the resources mentioned, visit JustinDonald.com/77 Get the Lifestyle Investor Book! To get access to The Lifestyle Investor: The 10 Commandments of Cashflow Investing for Passive Income and Financial Freedom visit JustinDonald.com/book Rate & Review If you enjoyed today’s episode of The Lifestyle Investor, hit the subscribe button on Apple Podcasts, Spotify, Stitcher, Castbox, Google Podcasts, iHeart Radio, or wherever you listen, so future episodes are automatically downloaded directly to your device. You can also help by providing an honest rating & review. Reviews go a long way in helping us build awareness so that we can impact even more people. THANK YOU! Connect with Justin DonaldFacebookYouTubeInstagramLinkedInTwitter See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.