Fundraising can be one of the most daunting tasks as a founder or even for a fund manager like me. If you just google how to fundraise, you get millions of results, a lot of conflicting information and it can all be overwhelming. Our guests today, Leslie Fine and Jonathan Lowenhar are looking to help solve that for founders by being a trusted source of coaching and advice with their startup advisory firm, Enjoy The Work. About Jonathan Lowenhar: Jonathan is an operator who successfully built a $1B business segment for a large public company, guided the turnaround of a distressed $100M+ revenue business, launched and sold a venture-backed startup, and led a B2B SaaS business to global-scale. In 2015, he founded Enjoy The Work, a firm of expert early-stage operators who have combined their considerable skills to advise the next generation of startups to launch, grow, and reach scale. About Leslie Fine: In 2008, Leslie founded Crowdcast, and successfully exited the company in 2012. Following Crowdcast, she helped lead three more startups, and landed at Salesforce to help launch their first AI product. She joined Enjoy The Work in 2019 as a General Partner. She has a PhD in Game Theory and Behavioral Economics from Caltech. In this episode we discuss: 01:21 Leslie’s journey into the startup ecosystem 03:43 Jonathan’s journey into the startup ecosystem 06:38 Why they had to leave her corporate job to return to startups 08:48 What about working with startups that excited Leslie 11:21 Why fundraising is so much more than building a pitch deck and hope isn’t a strategy 14:36 Other things founders need to think about when entering a fundraise and why being defensive is the death of a fundraising effort 17:52 Investors are looking for no, not looking for yes 19:02 Entrepreneurs need to understand that investors also have bosses, so make their jobs easy 22:14 Why fundraising is a sales funnel that deserves scrutiny at every stage of the process 24:48 Being arrogantly likable as a founder during a fundraising process 26:09 The four different playbooks for fundraising 30:22 Having a support person on the road to fundraising 32:00 The third rails of fundraising 41:42 Managing emotions during the fundraise 44:22 Warm intros vs. cold intros Leslie’s Fast Favorites Podcast The Indicator Newsletter/Blog Tomasz Tunguz Tech Gadget Theragun New Tredn Female Entrepreneurs Book Alice in Wonderland Life Lesson If it takes less than 5 minutes, just do it. Jonathan’s Fast Favorites Podcast The Bill Simmons Podcast Newsletter/Blog Scott Galloway Tech Gadget Air Fryer New Trend Soft Pants Book The Fountainhead Life Lesson Don’t keep score Follow Matt Cohen and Tank Talks here! Podcast production support provided by Agentbee.Agency