The Bootstrapped Founder

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. 

You can also watch this episode as a video on YouTube.

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.

You can also watch this episode as a video on YouTube.

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. 

You can also watch this episode as a video on YouTube.

As a creative entrepreneur, it is important to diversify your portfolio and have multiple projects in progress in order to reach a wider audience, stabilize income streams, and protect yourself from the risks associated with relying on any one platform. In order to do this, it is essential to own the means of communication with your audience, such as through a newsletter or blog, and to repurpose content for different formats. Additionally, it is important to collaborate with other creators, use social media to drive traffic to your own platform, and focus on building a community rather than just an audience. Finally, it is essential to regularly back up your work and data in order to protect yourself from being de-platformed.

- Diversify Your Creator Portfolio
- 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.

You can also watch this episode as a video on YouTube.

Today, I’m talking to Jay Clouse, a creative entrepreneur, and all-around amazing human being. We’re talking about keeping it all together as a solo creator, what makes a personal brand work, and how important authenticity is in building an audience.

00:00:00 What to do about all the attention-grabbing out there
00:05:00 A trust-based paradigm for your work
00:12:15 The importance of being a human being and not a brand
00:18:11 Challenges of aligning all of your projects under one umbrella.
00:23:02 Can you even find good names at the start?
00:28:57 The importance of having a backlog of ideas.
00:32:37 Will I ever get to this level of quality?
00:37:05 Choosing priorities
00:43:11 The mechanics of building community & building relationships with people
00:46:15 Teaching sentient beings to do things that are good for them (and good for you)
00:50:42 An audience is like an insurance policy

- Creative Commitments with Jay Clouse
- 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. 

You can also watch this episode as a video on YouTube.

Sharing your work and process in public can be difficult for introverted entrepreneurs and creators, but it can help build credibility and trust with your audience, gather valuable feedback and insights, and even lead to new opportunities. Tips for sharing in public include reframing why you do it, taking it slow and steady, breaking it into small chunks, scheduling posts, and engaging in conversations. Setting specific goals for the amount of sharing you want to do each week or month can help you stay on track.

- Realistic Building in Public for Introverted Founders
- 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. 

You can also watch this episode as a video on YouTube.

Today, I’m talking to Ana Bibikova, a defender and cheerleader for introverts in entrepreneurship. Ana knows what it means to be skeptical of loud and salesy marketing tactics. They might work great for extroverts, but not so much for the quiet types. Today, we’ll talk about how you can build a public-facing brand without resorting to all the obnoxious and much-too in-your-face tactics. We’ll talk about being introverted, working with introverts, and serving introverts. Here’s Ana.

00:00:00 Entrepreneurship and Introversion
00:10:13 Growing up being introverted without knowing what it is
00:16:57 A History of Introversion
00:22:49 The loud and shouty approach to social media
00:27:33 How do you stay quiet when you’re selling?
00:34:07 You’re the magnet for signals from the people around you
00:42:45 How to do self-promotion as an introvert vs. an extrovert
00:49:03 You attract what you put out, not what you say

This episode is sponsored by MicroAcquire. 

Here's the blog post for this episode.
You can also watch this episode as a video on YouTube.

Yesterday, the creator economy learned that Gumroad, a platform where creators have been building their businesses by selling their services and products, increased their prices significantly. That caused a lot of backlash in the community, with people threatening to switch to other platforms and criticizing how the price hike was communicated. It’s been an intense topic of community discussion.

Today, I am talking to Sahil, the CEO of Gumroad, about what prompted this change, what happened to cause such a stir, and where Gumroad is heading in the future. Here’s Sahil.

You can find this conversation on YouTube.

When it comes to selling a small indie business, defensibility is a key factor that potential buyers will consider. A unique moat, or competitive advantage, lets your business stands out from the competition and is seen as a valuable acquisition.

Many small founders sell their businesses because they want to get rid of them, and that attracts bargain hunters. It’s easy to negotiate a founder down when they feel pressure to sell a business that’s not very stable or profitable in the first place.

Being able to show that potential competitors have to climb a rather sizeable barrier to entry into your market will net you a significant premium when it’s valuation time. The absence of such a moat around your entrepreneurial castle will push down the price you can ask for. While buyers will still acquire profitable businesses without an oversized advantage, it’s a good idea to consider how you can set up a moat around your business. It will make things much easier.

- Build a Defensible Indie Business
- 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. 

You can also watch this episode as a video on YouTube.

Today, I am talking to Andrew Gazdecki, a pillar of the founder community and himself founder of the acquisition platform formerly known as MicroAcquire — but we’ll learn more about that on the show. Besides organizing millions of dollars worth of acquisitions every month, Andrew is a true teacher. His content on building software businesses is spectacularly useful. And fortunately, he will share a lot of it with us today.

00:00:00 Introduction

00:00:54 Founder and personality

00:04:19 MicroAcquire: the first venture

00:09:51 On being relatable

00:13:42 From B2B to Human2Humman

00:20:10 What was missing in the market?

00:27:07 What makes a business more sellable?

00:32:14 Tips for selling your business

00:39:07 Working in the business vs. working on the business

00:46:47 You can’t succeed without failure

00:52:59 Any exit, no matter how small, is a good step

This episode is sponsored by MicroAcquire. 

Here's the blog post for this episode.
You can also watch this episode as a video on YouTube.