Justin sits down with Helen Ryles and Michael Green, the two people behind almost every chat, email, and demo call that comes into Transistor, to talk about the company's secret weapon: the thing that converts 75% of trials to paid and keeps people around for years. Chapters: Quotes: From Helen: "The bar with customer support is really quite low across the industry... If companies are setting the standard of getting back to people in three to five business days, we don't have to necessarily adopt that. We can set our own standards." From Michael: "There is an emotional side to podcasting, to using a product, to creation, and we help on that side as well. People are often excited or nervous or panicking or something feels urgent, and we can help alleviate all of that emotional side. It's not just about questions and answers." Have feedback on this episode? 👉 ​Leave a voicemail here​ 🦋 📺

Justin and Jon reconnect after a two-year podcasting hiatus. What's happened since their last episode? Lots! They talk about big changes in their personal lives, and then move on to how they're thinking about Transistor as a business. These discuss burnout and motivation, the evolution of the podcasting industry, the pressure of being a leader, and the possibility of taking a sabbatical. The Transistor team is off to Banff for their annual retreat! Quote: "Working hard does not lead to burnout, but the lack of hope leads to burnout. So if you're working really really hard for something that you don't believe will pay off, it's super easy to lose motivation. And that has happened to me in the past! But! If you believe that the thing you're working on will have a payoff, the amount of work almost doesn’t matter." – Aaron Francis Links: The last episode Jon and Justin recorded together Aaron Francis' newsletter "Everything you've been told about burnout is wrong." Matt Wensing's tweet Have feedback on this episode? 👉 ​Leave a voicemail here​ 🦋 📺 Timestamps:

Harris Kenny was a long-time listener of the podcast, and dreamed about building his own software product. After multiple attempts, over 5 years, he finally did it. How? He shares his experiences transitioning from a corporate job to entrepreneurship. He also discusses the challenges of user engagement, the exploration of various SaaS ideas, and the importance of foundational work in entrepreneurship. Links: Harris Kenny on Linkedin OutboundSync - Integrate outbound campaigns in HubSpot and Salesforce IntroCRM (Archived) - Access Blocked How Loom Found PULL - Growth Strategy Case Study Follow Justin on Bluesky Have feedback on this episode? 👉 ​Leave a voicemail here​ 🦋 Reply on Bluesky Timestamps:

Bootstrapping a business is like getting a plane to lift off the ground. But what do you do once the plane is in the air? Dave Giunta and Justin Jackson recorded a recent phone call about maintaining motivation after the initial startup phase. How does founder energy shift once you've achieved your early goals? Dave prods Justin to find new sources of motivation – whether through mentoring junior team members, connecting with customers in fresh ways, or knowing when it's time to explore new horizons. They also discuss why Dave left Home Chef (after 8 years) and what he's doing next. Links: Follow Dave on Bluesky Connect with Dave on LinkedIn Follow Justin on Bluesky Have feedback on this episode? 👉 ​Leave a voicemail here​ 🦋 Reply on Bluesky Timestamps: 00:00:17 - Giuuuuuunta 00:01:15 - Chatting in Guatemala: maintaining motivation, remote work, career transitions 00:02:12 - Motivation in early vs late stage startups 00:06:00 - Challenges with maintaining motivation once the business is established 00:15:35 - Working with different team member motivations 00:26:42 - Importance of understanding individual team members 00:29:20 - Remote work advantages and challenges 00:35:35 - Working with junior team members and mentorship 00:54:00 - Why Dave left Home Chef after 8+ years 00:57:00 - Discussion of career transitions and giving yourself space to explore 01:02:20 - Future plans and exploration after leaving long-term role

How do founders of small bootstrapped companies hire new employees? Adam Wathan got over 1600 people who applied for two new roles at Tailwind Labs (a small team of six people). They ended up hiring two people, but neither of them actually applied. This wasn't how Adam expected (or hoped) this process would go. There were lots of surprising takeaways and lessons learned from the whole experience. "If you figure we spend 5 minutes on every single application, that was like 133 hours straight reading applications. Processing these job applications was basically my full time job for 2 months." – Adam Wathan Links: Hackers Inc podcast Tailwind job opening announcement Design Engineer job posting Staff Software Engineer job posting Reddit: 11 months of job searching visualized Have feedback on this episode? 👉 ​Leave a voicemail here​ 🐦 Reply on Twitter Timestamps: