Justin Jackson Host

Justin Jackson

Co-founder of Transistor.fm

Appears in 159 Episodes

#160

Giuuunta! Motivating yourself when you're not in startup mode

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 BlueskyConnect with Dave on LinkedInFollow Justin on BlueskyHave feedback on this episode?👉 ​Leave a voicemail here​🦋 Reply on BlueskyTimestamps:00:00:17 - Giuuuuuunta00:01:15 - Chatting in Guatemala: maintaining motivation, remote work, career transitions00:02:12 - Motivation in early vs late stage startups00:06:00 - Challenges with maintaining motivation once the business is established00:15:35 - Working with different team member motivations00:26:42 - Importance of understanding individual team members00:29:20 - Remote work advantages and challenges00:35:35 - Working with junior team members and mentorship00:54:00 - Why Dave left Home Chef after 8+ years00:57:00 - Discussion of career transitions and giving yourself space to explore01:02:20 - Future plans and exploration after leaving long-term role
#158

Is ONCE enough?

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?Links:Once landing pageCampfire sales pageDHH's tweet: "ONCE/Campfire hasn't even been for sale for a week, but we've already sold more than quarter of a million dollars."Tyler Tringas's videoI want to hear your thoughts:If you listen to the episode, I'd be curious to hear your thoughts:Can you think of a low-price, pay-once, on-prem software product that's succeeded? (The only one I could think of was ​Statamic CMS​)Do you think a different Once product might have made more sales? What kinds of products do you think might work?Did you buy Campfire? What did you buy it for? Are you using it as a chat tool for your company?Other thoughts on our discussion.👉 ​Leave a voicemail here​🐦 Reply on TwitterTimestamps:(00:00:00) - "I appreciate that 37signals exists."(00:01:58) - 37signals' influence in the bootstrapped startup space(00:03:58) - What did we expect from the Campfire/Once launch?(00:06:23) - DHH's tweet on Campfire sales – is that what we expected?(00:09:49) - The Once model, philosophy, and Campfire's history(00:17:21) - Misconceptions about what IT Managers want(00:19:49) - How Campfire was marketed and positioned(00:26:01) - Basecamp's PR, virality, and audience (00:28:29) - Can you do customer research to validate demand?(00:32:01) - The volume of sales as a success metric(00:33:33) - The Potential for Campfire's expansion(00:37:37) - Distribution opportunities with hosting providers00:39:31) - The intuition behind HEY Email's success(00:43:42) - The Value of an Audience and Customer Overlap(00:45:12) - The Compounding Advantage of Longevity(00:49:54) - Scorecard
#157

How Ben and David bootstrapped the Acquired podcast

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(0:24:18) – How they got their first podcast sponsors (and why it wasn't about making money)(0:27:58) – Why they give their sponsors a white glove, 11-star experience(0:34:13) – How to get more word-of-mouth referrals for your podcast(0:37:00) – Acquired's unconventional approach to podcast ads(0:41:54) – How the Acquired podcast's growth machine works(0:48:05) – Why their NVIDIA podcast episode went viral(0:50:48) – Why they switched from Libsyn to Transistor for podcast hosting(0:57:18) – The rise of the "independent, boutique podcaster."(1:02:27) – "The future of podcasting doesn't belong to Gimlet, NYT, NPR..."(1:06:22) – David Rosenthal's advice to aspiring podcasters
#156

Nashville team retreat: scary birds, country music, and a photo shoot

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"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." – HelenLinks:Photos from our trip to Nashville. PhotoWalk Nashville service.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.A retreat is a great time for a remote team to celebrate milestones and achievements.Have a balance between work activities and fun activities.Simple activities like games or cards can be as fulfilling as fancy events.
#146

Super Fun SaaS Sales Tax (Part Deux)

Last week's episode hit a nerve! "The idea that every small software company in the world will be able to be in perfect compliance will every foreign federal, provincial, state, and municipal government that imposes a sales tax is ridiculous. It's an impossible task.Broadly, there were a few different camps with the responses we received: North American SaaS companies who have been using Stripe:  "Yes! Sales tax compliance for SaaS is brutal."European SaaS companies that have had to deal with VAT for a long time (many of whom use a Merchant of Record).Smaller North American solopreneurs and companies who had no idea they needed to collect and remit sales tax internationally.North American companies who have one-time sales and use Merchant of Record services.Responses from indie hackers:European: “Once again, I notice that the indie hacking community has a somewhat naïve approach to what running a business actually entails. As a European, not having a plan for sales tax is... mindboggling.”Cooper: “I think it might be a European perspective; we are dealing with VAT from day 1, so it's just one of the parts of running a business from the start, it can't really be neglected.”Edwin Saraccini: “To clarify, [for Canadians] this is absolutely new territory (Debated in parliament for years) and recently put to legislation in 2021.”Daniel Vassallo: “It's impossible to be compliant everywhere. The Kingdom of Tonga could tomorrow come up with an internet tax and require you to remit 25% of your sales to the tax office in person in their local currency. And they won't tell you about it. It's just a cost/benefit analysis.”Derrick Grigg: “How can they enforce tax collection on a business they have no jurisdiction over? Governments are shaking businesses down. I’m all for collecting and paying properly where you physically operate but collecting and remitting outside your province never mind nation is a stretch.”Derrick Reimer: “Dear Stripe: We SaaS founders are desperate for a full-stack global tax compliance solution without having to leave you for a merchant-of-record. Are you planning to solve this?”Did you know..."There are actually several different types of sales tax systems in use throughout the United States. The biggest difference is whether the seller or the purchaser is the main taxpayer. In some states, the tax is imposed on sellers, who then have the option of passing the tax along to their purchasers. In other states, the tax is imposed on the purchaser, with the seller being responsible for collecting the tax and remitting it to the state. And then there are other states where the liability for the tax is shared by sellers and purchasers." (Source)New thoughts on Sales tax complianceI still haven’t heard from anyone who has successfully migrated a “mature” SaaS from Stripe to Paddle or LemonSqueezy. These are no-gos:Can’t cause more churn.Can’t require customers to re-enter information.Can’t change our checkout experience.We might consider Paddle / LemonSqueezy if:Their fees were more affordable (compared to our existing fees it would be ~$63K year more, $5,250 per month more)Their dev experience had a better rating from the folks we know.I had heard from anybody who was at our stage and had actually migrated successfully.A few folks suggested Revin, which promises “simple global sales tax compliance for Stripe for only $499/month,”  but:They have to “create a new Stripe account for your brand.”Do they own your Stripe account?You’ll lose your historical stats and revenue analyticsThe current solution we’re considering is Stripe Tax + TaxJar (and start with US and Canadian tax remittance)
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