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:
(02:13) - What did Helen do before she joined Transistor?
(03:00) - What did Michael do before joining Transistor?
(05:05) - How does Transistor do customer support different?
(08:04) - What have we learned by doing demo calls with customers?
(12:32) - What are some of the emotions of starting a podcast?
(16:15) - What can startups learn from being a customer led company?
(18:44) - How do we approach AI in customer support?
(22:50) - How does customer support translate into sales?
(25:49) - What else does a customer support role do at a Saas?
(33:41) - How do future generations learn how to be on a team?
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."
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
(00:30) - Where has Jon been for the last 2 years?
(08:56) - What's Justin been up to?
"Justin, I built a SaaS!"
Episode 161
Tuesday, June 24, 2025 • Duration 01:30:43
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.
(11:03) - When you don't have a boss, do you have the drive to go get work?
(15:45) - How did you hear about saas businesses?
(27:02) - Recognizing a need and building something for it
(34:44) - So many opportunities in inventory software
(41:03) - The difficulty of getting people to just log in
(49:18) - The saas that worked
(01:01:01) - Where are you getting new customers from?
(01:06:47) - Using Tinyseed as a bridge
Giuuunta! Motivating yourself when you're not in startup mode
Episode 160
Monday, December 9, 2024 • Duration 01:11:56
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.
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
Adam Wathan: how small startups hire employees (Tailwind CSS)
Episode 159
Tuesday, June 4, 2024 • Duration 01:34:42
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
(03:40) - What's the size of Transistor and when did you last hire?
(05:24) - How did you meet or find your employees?
Is ONCE enough?
Episode 158
Saturday, February 10, 2024 • Duration 01:10:58
A panel discussion on 37signals' first ONCE product, the launch of Campfire ("pay for it once, install it, and run it on your own server"). Ian Landsman, Tyler Tringas, and Justin Jackson share what they expected to happen before the launch, what did happen, and what it means for indie hackers and bootstrappers who want to launch SaaS companies. Is this the end of SaaS?
How Ben and David bootstrapped the Acquired podcast
Episode 157
Thursday, January 25, 2024 • Duration 01:07:50
Fast Company called Acquired "the #1 tech podcast sensation." I've been a huge fan of the show for years. So, I was surprised when they contacted me and wanted to switch to Transistor for podcast hosting!
Since switching, they've had a breakout year. Their clips started showing up everywhere on my social media feed; they had chart-topping episodes on Nintendo, Nike, and Costco, and they interviewed the CEOs of NVIDIA, Uber, and Charlie Munger.
And this was the year that Ben Gilbert and David Rosenthal (the co-hosts) both went full-time on the podcast. Podcasting is now their job.
With all of that activity, I thought Build your SaaS listeners would be interested in hearing my interview with David about their entire story:
How they got started, how they built momentum over time,
how they were able to double their audience every single year since 2015,
And how that momentum ended up Attracting an incredibly valuable audience that they've now monetized through sponsorships.
This interview has so much that podcasters, creators, and indie entrepreneurs will find super helpful and inspirational.
🔥 Key moments:
(0:00:00) – A breakout year for Acquired
(0:01:45) – What is the Acquired podcast about?
(0:02:40) – How the Acquired podcast got started (origin story)
(0:07:23) – How Ben and David's co-hosting relationship works
(0:09:00) – The 3 big goals that made them want to start Acquired
(0:11:38) – How did listeners respond to the first episodes?
(0:14:55) – The best reason to start a podcast
(0:15:30) – The secret to how Acquired attracts new listeners
(0:18:13) – How they got featured in Apple Podcasts, Overcast, Pocket Casts, and Spotify
Nashville team retreat: scary birds, country music, and a photo shoot
Episode 156
Tuesday, September 26, 2023 • Duration 44:35
The whole team is on the show! Jon, Helen, Jason, Josh, and Justin are on the mics to discuss our recent team retreat to Nashville, Tennessee. If you're wondering what a retreat looks like for a remote team, you'll get a lot out of this episode. We also reveal some of our exploits in Music City:
"Going to a Tiki Bar is usually a mistake."
Highlights
(00:10) - Welcome
(01:10) - Highlights of our retreat in Nashville
(12:55) - It's not easy to get everyone together
(20:26) - Our schedule for the retreat
(26:24) - Electrolytes are a good idea
(31:49) - Things to improve or tips for other teams
"For 51 weeks, our small team works efficiently. Our team retreat week is a culmination of celebrations, milestones, birthdays, and holidays we might have missed. It's special to condense these moments into one week and see everyone in person to celebrate our achievements from the previous year." – Helen
SurfOffice Location Finder: "Discover the optimal location to meet with your remote team. Results are sorted by average travel time per person, number of stopovers, and overall price."
How to plan a team retreat: Planning a retreat can be a daunting task, so we wanted to share our learnings in the hopes that it’ll be helpful for other remote teams out there.
Takeaways:
The city you choose for your retreat will significantly influence the team's productivity and leisure activities.
Be intentional and set aside time for planning and product discussions.
Paul Jarvis: gaining freedom by building an indie business
Episode 155
Tuesday, August 1, 2023 • Duration 01:10:40
Justin catches up with his old internet friend Paul Jarvis. Today, Paul co-founded Fathom Analytics with Jack Ellis: a simple alternative to Google Analytics. Paul is also the author of the book "Company of One," which has influenced a whole generation of indie entrepreneurs (and has been reviewed by Cal Newport, Chris Guillebeau, Ben Chestnut, Tiago Forte, and more). Previously, Justin and Paul did a weekly mastermind, where they supported and encouraged each other around our indie businesses. They decided to do a catch-up call and recorded it so you could listen in. 👍
Highlights:
(00:10) - Intro
(02:15) - Being off the internet
(03:53) - What's a typical day for Paul?
(06:16) - Looking back at our Mastermind call
(08:03) - There's no beginning and no end
(10:31) - Things that are out of your control affect your business
(13:03) - Does Justin's surfing metaphor make sense to a surfer?
(16:06) - How would you start an indie business in 2023?
(22:00) - You've got to get in motion
(25:03) - Using products in your category for a long time
(27:48) - Is there still any room in Saas?
(31:51) - The act of making the bet
(38:40) - Is freelancing still viable in 2023?
(42:50) - Company design is lifestyle design
(44:55) - Worrying about being stagnant
(47:15) - How do you handle customer feature requests?
(52:03) - It's ok to be late to a shift in the market
(58:19) - Caring is an indie advantage
(01:05:00) - Collaboration is what gets us anywhere
🎙️ Podcast hosting is provided by
How Tim worked on side-projects for 10+ years, and finally went full-time (with kids)
Episode 154
Tuesday, June 20, 2023 • Duration 54:14
Tim reached out after the Aaron Francis episode: "I wanted to pitch you on the idea of coming on the podcast and sharing my journey of building side projects for the last decade while raising a family. I can also share the guardrails I put in place before finally going full-time on T.LY."
Highlights:
(00:12) - Welcome
(01:13) - Who is Tim Leland?
(03:20) - What guardrails did you put in place?
(06:24) - What's the sales funnel?
(08:13) - Family as a motivator
(16:21) - How would you describe your effort during this process?
(20:06) - What about family boundaries?
(23:25) - How do you manage your thoughts?
(31:15) - How have you been able to manage the effort level?
(34:44) - The pressure of cutting the cord from your job
(38:16) - What's it been like being full time on t.ly?
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