The Bootstrapped Founder

Brennan shares the secrets to using emails to build relationships and increase your revenue.Today, I’m talking to Brennan Dunn, the founder of Palladio, co-founder of RightMessage, and general email expert. As a newsletter author myself, I took to this opportunity to learn as much as possible about personalizing and optimizing my email strategy. You’ll also hear what most people get wrong in email marketing. Here’s Brennan.00:00:00 Brennan Dunn00:00:48 What is up with email clients?00:05:05 Integrating with large platforms00:08:34 Maybe build a competitor?00:12:12 Emails and metadata00:16:20 Email personalization and how it works00:22:07 How do you get started with this?00:25:28 Focusing time and effort on certain platforms00:31:24 The difference between an email list and a newsletter00:36:30 The importance of segmentation00:41:06 Use segmentation to increase your list00:48:56 Customer centric marketing00:54:24 Is email the right medium to de-risk?00:59:20 Don’t over-saturate- Mastering Email Marketing with Brennan Dunn - 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 entrepreneurshipThis episode is sponsored by MicroAcquire. You can also watch this episode as a video on YouTube.

To increase your chances of success as an entrepreneur, think outside the box and expand your opportunity surface. This can be achieved by embracing activities that don't scale, diversifying inputs, and taking small steps toward achieving your goals. These strategies will help you create valuable connections, build strong relationships and gain valuable insights that will lead to success.00:00:00 Laura's journey00:01:10 The parable of the monkey and the pedestal.00:02:28 A cultural problem00:03:36 Reflecting on the monkey- The Monkey and the Pedestal- 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 entrepreneurshipIf you're interested in Descript, go and check it out here.You can also watch this episode as a video on YouTube.

Today, I’m talking to Laura Elizabeth. She co-hosts the Non-Tech Founders podcast and runs several products as a non-technical founder. We talk about outsourcing, trust, and building an audience around your business. Here’s Laura!00:00:00 Laura Elizabeth00:02:10 Running a non-technical founder podcast00:09:28 Hiring the right people00:12:14 Hiring people who can do something you can't00:17:27 Being able to do everything is both awesome and frightening 00:20:13 Experimenting with different modes of delegating00:25:45 Establishing an internal process for your business00:30:00 On Phrasing00:36:30 The importance of having a mentor00:42:04 Providing the fertile ground for luck to strike00:45:04 The hardest part is overcoming your inner demon00:52:56 Why it's good to have an expert for website personalization00:56:33 Where you can follow Laura- Building Software Products As a Non-Technical Founder With Laura Elizabeth- 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 entrepreneurshipThis episode is sponsored by MicroAcquire. You can also watch this episode as a video on YouTube.

To increase your chances of success as an entrepreneur, think outside the box and expand your opportunity surface. This can be achieved by embracing activities that don't scale, diversifying inputs, and taking small steps toward achieving your goals. These strategies will help you create valuable connections, build strong relationships and gain valuable insights that will lead to success.- Expanding Your Opportunity Surface- 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 entrepreneurshipIf you're interested in Descript, go and check it out here.You can also watch this episode as a video on YouTube.

Today, I’m talking to Daniel Fayle — co-founder of Chekkit, a business he and his team have boostrapped to $2mil in ARR. We’ll touch on finding the right vertical to get started, how to do things that don’t scale, and what choices need to be made to get a business to 7 figures. 00:00:00 Daniel Fayle00:05:35 Getting started with Chekkit00:09:00 Local marketing & picking verticals00:12:05 When to hire a team?00:17:25 Integrations00:22:33 Pricing choices00:25:32 How to be inspired by competition?00:29:54 The importance of customer support00:36:31 Setting limits on free trials00:41:55 Use the tech that your customers use00:47:15 How to stay on top of your game- Door-to-door to $2M ARR with Daniel Fayle- 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 entrepreneurshipThis episode is sponsored by MicroAcquire. You can also watch this episode as a video on YouTube.

I was chatting with Marissa Goldberg about remote work this week, and she gave me several handy frameworks for founders who want to build remote-first businesses. At the center of any successful remote work relationship lies trust.And surprisingly, many businesses have a tough time trusting anyone once they can't see them at their desk in the office. Remote work is throwing a wrench in the time-honored tradition of butt-in-seat-hands-on-keyboard that so many managers consider to be the pinnacle of productivity.Remote work does away with this.00:00:00 Remote Work is Here to Stay00:01:28 Async is the New Default00:04:42 The Deep Work Zone00:06:17 Trust and Having Nowhere to Hide- The Role of Trust in Remote Work - 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 entrepreneurshipYou can also watch this episode as a video on YouTube.

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 Workplaces00:02:03 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 entrepreneurshipThis 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 Intro00:00:29 Sponsor00:01:44 Introduction00:02:50 Balancing Parenting & Business00:04:58 Overthinking00:06:22 Addictions00:08:03 Dealing with Failure00:09:45 Not delegating can lead to anxiety00:11:13 Burnout & Dreading Loss00:12:49 Navigating imposter syndrome when others appear successful00:14:44 Second-guessing decisions and dealing with incomplete data00:16:29 Underestimating and Judging Yourself00:18:14 Debilitating Shiny Object Syndrome 00:19:54 Feeling guilty for taking a break00:21:09 Underwhelming Sales00:24:03 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 entrepreneurshipThis 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 Introduction00:01:04 Patrick's entrepreneurial journey00:03:10 A different approach to marketing00:06:23 Help Sells: providing free value and then selling00:13:53 Dealing with a $200mil exit00:15:55 Filming a documentary while exiting00:19:03 Keeping the company running during the sale00:24:42 Anxiety during the sale00:28:08 Anxiety AFTER the sale00:34:12 Jumping right back into work00:37:28 Building trust with your team00:41:49 Defining your role in a deal00:45:05 Will Patrick ever take a vacation?00:49:38 It never ends: mental health for founders00:54:05 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 entrepreneurshipThis 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 entrepreneurshipThis episode is sponsored by MicroAcquire.You can also watch this episode as a video on YouTube.