179: Founder Mental Health Pitfalls
The Bootstrapped Founder
01/06/23
•24m
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This week I chatted with Patrick Campbell about his exit of ProfitWell to Paddle for $200 million. One of the most mind-blowing things that I experienced during that conversation was hearing Patrick tell me that he feels he needs to build something else to prove that his exit -$200 million- was not just a fluke.
I did not expect that, but I should have because I feel the same way all the time. And the more founders I talk to, whatever stage of their journey they might be on, I hear them tell me the same story too. Whether they just started out or sold their business for millions a few years ago, they still struggle with who they are, what they should be doing, and proving themselves and their worth to others.
00:00:00 Intro
00:00:29 Sponsor
00:01:44 Introduction
00:02:50 Balancing Parenting & Business
00:04:58 Overthinking
00:06:22 Addictions
00:08:03 Dealing with Failure
00:09:45 Not delegating can lead to anxiety
00:11:13 Burnout & Dreading Loss
00:12:49 Navigating imposter syndrome when others appear successful
00:14:44 Second-guessing decisions and dealing with incomplete data
00:16:29 Underestimating and Judging Yourself
00:18:14 Debilitating Shiny Object Syndrome
00:19:54 Feeling guilty for taking a break
00:21:09 Underwhelming Sales
00:24:03 Outro
- Founder Mental Health Pitfalls- Find your Following, my Twitter course — now with Find your Following Essentials, the 7-day Twitter crash course
- Zero to Sold & The Embedded Entrepreneur, my books on entrepreneurship
This episode is sponsored by Senja.
Previous Episode
178: Patrick Campbell — Life After a $200mil Exit
January 4, 2023
•61m
Today, I’m talking to Patrick Campbell, founder of ProfitWell, a bootstrapped business that recently got acquired by Paddle for a whopping 200 million dollars.
I talked to Patrick about getting acquired for 9 figures, finding your footing as a founder after such an incredible exit, where the online payment industry is heading, and how mental health challenges follow us wherever we go.
00:00:00 Introduction
00:01:04 Patrick's entrepreneurial journey
00:03:10 A different approach to marketing
00:06:23 Help Sells: providing free value and then selling
00:13:53 Dealing with a $200mil exit
00:15:55 Filming a documentary while exiting
00:19:03 Keeping the company running during the sale
00:24:42 Anxiety during the sale
00:28:08 Anxiety AFTER the sale
00:34:12 Jumping right back into work
00:37:28 Building trust with your team
00:41:49 Defining your role in a deal
00:45:05 Will Patrick ever take a vacation?
00:49:38 It never ends: mental health for founders
00:54:05 The future of the payment industry
- Life After a $200mil Exit with Patrick Campbell
- Find your Following, my Twitter course — now with Find your Following Essentials, the 7-day Twitter crash course
- Zero to Sold & The Embedded Entrepreneur, my books on entrepreneurship
This episode is sponsored by MicroAcquire.
Next Episode
180: Marissa Goldberg — Running a Remote-First Business
January 11, 2023
•60m
Today, I’m talking to Marissa Goldberg. She’s an expert in remote work and guides companies and founders alike toward a future-proof workplace. We’ll talk about productivity, best practices for going remote, and setting up a remote team of all sizes. Here’s Marissa.
00:00:00 Remote Work and Future Proof Workplaces
00:02:03 What is Remote Work Prep?
00:06:54 The right approach to go about remote work.
00:11:00 Traditional hiring doesn’t work for remote teams.
00:17:29 Integrating rest into your work.
00:23:10 The perversion of productivity & responsiveness policies.
00:27:27 Issues with video calls.
00:31:02 The difference between a conversation and a phone call.
00:37:12 How to transition from pandemic remote to normal remote.
00:41:10 The culture of control and top-down decision-making.
00:45:29 There’s no place to hide with remote work.
00:51:58 How do you keep doing what you do?
00:56:23 What is impostor syndrome? What is it and why does it exist?
- Running a Remote-First Business with Marissa Goldberg
- Find your Following, my Twitter course — now with Find your Following Essentials, the 7-day Twitter crash course
- Zero to Sold & The Embedded Entrepreneur, my books on entrepreneurship
This episode is sponsored by MicroAcquire.
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