I’m so incredible excited to be able to present this Founder Advice with Jessica Brondo Davidoff. I’ve now known Jess for close to seven or eight years, and it’s been an incredible journey seeing both our careers and families grow. She’s incredibly talented, tenacious, and has an acute sense of honing in on what a company needs most.

She’s exited a number of companies, among them Admittedly, and GolfMatch, and has recently shifted her skills to helping businesses meet the challenge of COVID19. I’m so excited to share her experiences with you, so let’s begin: Founder Advice with Jessica Brondo Davidoff.

How’d you get started as an entrepreneur? 

Technically my first “business” was a nail salon in my parents basement where I would offer force my mom’s friends to get pedicures from my younger brother. I started my first adult business at 22, when after working for less than a year at an SAT prep company, I had a hypothesis that the ACT was about to take off, and so I quit my job, got a bartending job at night to pay the bills and spent 6 months writing ACT prep curriculum for my first company, The Edge. Fortuitously, the ACT started to become extremely popular and my company essentially blew up without any sort of marketing.

What do you perceive as your biggest professional success? 

Freedom! As someone who has been an entrepreneur for over 15 years, the thing I value most is the freedom that entrepreneurship offers. Having control over my schedule, the things I’m working on and with whom I’m working is something I would never trade.

And now the hard one, what would you say is the biggest hardship that you had to go through professionally?

I’ve become somewhat of a “wartime CEO” and turnaround specialist, which has the unfortunate burden of restructuring teams. No matter how many people I’ve had to let go from portfolio companies, it never gets easier and has resulted in a very strong (but healthy) relationship with red wine.

What has time as a CEO taught you about the way you approach life problems? 

I live and breathe by a quote from A League of Their Own – “It’s supposed to be hard. If it was easy, everyone would do it. It’s the hard that makes it great.” And I truly believe that the more you have to struggle along the way, the more you’ll appreciate the destination. 

When you have a tough problem to solve – who are the people you reach out to for help? Be it to pick their brains, work through concepts, etc… 

One of the things I’m most grateful for is the network I’ve been able to build over my career and I’m so lucky to have so many unique problem solvers in my pocket, especially my dad – my OG consigliere. I am also extremely lucky to be part of the Princeton alumni network and our online discussion groups are absolutely incredible for getting advice from some of the smartest people in the world.

When it comes to being a founder and CEO, what gets you out of bed every morning?

Solving complex problems. My nickname is “The Wolf” – if you’ve seen Pulp Fiction, you’ll get the reference. 

How do you think tech entrepreneurship has changed since you started out? 

I think it’s become more inclusive and approachable. There are so many incredible resources out there to help people get their ideas prototyped – in addition to tools people can learn so they can prototype something themselves. However, I do think that funds have become MUCH more focused on business models. When I was raising money for my tech startups – Golfmatch and Admittedly, we had no revenue and a very long path to starting to generate revenue and had no issues raising money. I don’t think that type of funding is happening any longer.

What one piece of advice would you give founders starting today?

Make time for yourself. As a founder, your to do list will be never ending and you can stay up until 2am every night and never get to the bottom of your list, which is why it is so important to set a quitting time, and put things that are important to you – whether it’s running, painting, sailing, etc – into your calendar like you would the rest of your meetings. Also, you should view your email inbox as a to do list that you have no control over so make sure that instead of just focusing on getting through your inbox that you’re setting aside time to focus on what really matters to your company.

And what would you say is the biggest mistake you see founders make that is just so obvious to you now that wasn’t when you started? 

If you aren’t a finance person, get an incredible financial partner from the start to help build a sustainable road map and help keep you on its path. At my earlier startups, I always felt like the outsourced CFOs we were using were doing the equivalent of a doctor giving me my blood-work and having me interpret it, which is why after selling my third company, I founded Sprezzatura.

Lastly, anything awesome to say specifically to the amazing new female founders out there? 

One thing I’ve noticed over the past 15 years is that unlike men, women have an incredibly hard time giving each other critical feedback, and instead will bottle up frustrations and talk about their frustrations with others. This is incredibly detrimental to a company’s culture which is how toxic cultures were created at companies like Away and Outdoor Voices. My hope is that female founders will become more comfortable giving critical feedback immediately and in private in order to preclude the workplace toxicity that has become so pervasive among female-led brands.

As a turnaround and crisis management specialist, any advice for founders during the current COVID19 cris?

Crises are great truth tellers and will expose organizational, operational, strategic, and communication strengths and weaknesses. However, they also provide an opportunity to take risks and be creative. As you’re creating your road map, definitely avoid making decisions in silos. For example, your finance team shouldn’t be making cost cutting decisions without consulting with your marketing team and vice versa. Make sure that there is cohesive collaboration across your organization and over communicate with your team, providing different pieces of information to different levels of employees.

If you enjoyed Founder advice with Jessica Brondo Davidoff, check out some of our other Founder Advice interviews.

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