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 ecosystem03:43 Jonathan’s journey into the startup ecosystem06:38 Why they had to leave her corporate job to return to startups08:48 What about working with startups that excited Leslie11:21 Why fundraising is so much more than building a pitch deck and hope isn’t a strategy14:36 Other things founders need to think about when entering a fundraise and why being defensive is the death of a fundraising effort17:52 Investors are looking for no, not looking for yes19:02 Entrepreneurs need to understand that investors also have bosses, so make their jobs easy22:14 Why fundraising is a sales funnel that deserves scrutiny at every stage of the process24:48 Being arrogantly likable as a founder during a fundraising process26:09 The four different playbooks for fundraising30:22 Having a support person on the road to fundraising32:00 The third rails of fundraising41:42 Managing emotions during the fundraise44:22 Warm intros vs. cold intros

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