Chris Bakke is the co-founder and CEO of Laskie. Previously, he was the co-founder of Interviewed (acquired by Indeed), COO of 42Floors (acquired by Knotel), and managed business development for Zillow and RentJuice (acquired by Zillow). On this episode, Chris discusses his experiences selling his companies and then working for the acquirers such as Zillow and Indeed during the pandemic. He also discusses the growth of the freelancer economy and how companies are starting to think about their approach to full-time employees vs. contract workers. Finally, they talk about founding Laskie, Twitter and the founders-dilemma of deciding whether to sell when an offer comes by or continuing to build. Enjoy! (02:18) - Chris’ Background Working for Early Stage and Public Tech Companies (04:42) - What was it like working at Indeed in the midst of the pandemic? (07:47) - What is it like to transition from a founder of a company to being an employee after an acquisition? (10:09) - When you take on the new role do you know what’s required of you from the jump, or is it expected your role might change? (13:01) - Are there questions that you wish you asked in previous acquisitions to understand what it will be like on the other side? (15:13) - How did the idea for Laskie come about? How do you describe what y’all do? (19:02) - How long does it take to get approved as a vendor? (21:14) - How many times do companies hire full time people when a freelancer would do just fine? Are we entering a world where companies cut down on full time people in exchange for more freelancers? (24:31) - How do you overcome the issue of freelancer loyalty between competitors? (28:23) - Personality Testing in Freelancing (30:40) - Should hirers think about the idea of 1-3 days of working on a project with a potential employee before deciding to hire them? (36:04) - Has there been anything unique in this COVID era in terms of requested services you’ve seen? (39:18) - Chris’ Experience Working With the Same Group of Founders for All of His Companies (40:10) - Are the roles of the group pretty clear each time you start a company together? (45:31) - Was there someone who told you to stop doing founder-led sales and bring someone on or was it something you had to figure out? (47:07) - What is “the game” of being a venture-backed company? (50:19) - Was your goal to be the next billion-dollar company or did you know you wanted in and out in two years? (53:22) - Do you think there’s a lot of companies that should have sold much earlier but keep pushing for that $10B sale? (56:42) - What did it do to your psyche when you saw that first offer from a founder's perspective? (1:01:45) - Why are you bullish on San Francisco/Silicon Valley? (1:05:47) - If you were CEO of Twitter for the next year, what would you do? (1:09:17) - Do you have a childhood experience that put you on your life path? (1:12:20) - If you had a billboard on the busiest highway in Danville, what would it say? (1:23:43) - How can people reach you? Twitter: www.Twitter.com/ChrisJBakke LinkedIn: www.linkedin.com/in/bakk3/