Justin Jackson

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

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 WathanLinks:Hackers Inc podcastTailwind job opening announcementDesign Engineer job postingStaff Software Engineer job postingReddit: 11 months of job searching visualizedHave feedback on this episode?👉 ​Leave a voicemail here​🐦 Reply on TwitterTimestamps:

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

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

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.

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:Links:Fathom Analytics (get $10 off)Book: Company of OneArticle: How to Start a MastermindWayback Machine: Mint AnalyticsArticle: Why we moved from courses to SaaSSelf-Publishing Hangout: Paul Jarvis, Nathan Barry, Sacha Greif, Justin Jackson

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:Links:Tim's startup: T.LYTim's TwitterTim's blog: tools for marketers

This week Jon and Justin are joined by Marcella Chamorro. Previously, she worked in startup marketing but has recently transitioned to coaching founders and teams. We discussed how startup founders and their team members can realize their full potential.Here are some highlights:Quote:"I think people who choose to do coaching want to be really good at what they do and they want to have a really good life. They are looking to optimize their time on planet Earth."  – MarcellaLinks:Subscribe to Marcella's newsletterMarcella’s coaching websiteCheck out Marcella's articlesMarcella on LinkedInMarcella on Twitter

In this podcast episode, Michele Hansen (Geocodio) gives us an update on Section 174 and provides her take on "bootstrapping with kids."Michele explains you can be a part of the Small Software Business Alliance, and fight Section 174. If you're in the USA, please contact Congress! In the second half of the episode, Justin and Michele talk about the challenges of balancing starting a business while you have young kids. For more on this topic, check out the last episode with Aaron Francis.For more context on Section 174, check out our previous episode with Michele.

In this episode, Justin speaks with Aaron Francis about being a new parent and trying to bootstrap a startup. Aaron argued the other side of Justin's tweet thread: "Wait until your kids are older to start a company." Aaron is well-positioned to talk about this because he has twins and is also bootstrapping Hammerstone with his co-founder Colleen. The whole conversation is a nuanced take on the topic and full of important insights, especially on:the risks involved (especially if you're not working a full-time job)the kind of foundation (mentally, financially, emotionally, relationally) you need to be able to take the riskHighlights from this episode:

Jon and Justin welcome Joshua Anderton to the Transistor team! Josh is an amazingly talented full-stack web developer (Laravel, Rails, Tailwind CSS, Alpine, and more!) He's been helping us as a part-time contractor since Oct 2022, and we're excited to have him on board full-time! In this episode, we discuss why we hired another person and how we think about hiring at Transistor.Links:Joshua's personal siteJoshua's podcast: Getting to RamenJason Cohen's articleAcquired.fm is now on Transistor!

Michele Hansen (co-founder of Geocodio) is raising the alarm about Section 174. This legislation could dramatically increase your tax bill this year if you're a small software company in the USA. Michele is organizing a response through the Small Software Business Alliance.👉 ACT NOW:Sign up for Michele's listUS citizens: tweet and call your Senators today. They need to know that this is a small business issue and that small businesses in their state are hurt by Section 174.Share the ssballiance.org URL with your founder friends.In this episode:

Jon's back from his first real vacation in years. In this episode, we discuss how we've been removing inactive accounts on Transistor, SVB, Section 174, Revin is shutting down their Merchant of Record service, SaaS sales tax compliance:Links:Matt Levin's excellent summary of the Silicon Valley Bank runIan Landsman: "This is why I don't use startup-friendly banks (Mercury, etc)"Section 174: join ssballiance.orgRevin has shut down its Merchant of Record serviceFlurly (another Merchant of Record) was shut down by StripeFrom the Revin email:“The most relevant reason [we are closing] is that the Merchant of Record model is too risky for both sellers and the MOR operator. Sellers bear the risk of platform shutdown (as seen in the example of Flurly & Stripe), and the MOR operator could potentially become involved in illicit or illegal activities quickly, which could lead to all sorts of problems.Furthermore, it became increasingly clear that the Merchant of Record model primarily appeals to small-scale sellers or businesses with questionable and high-risk business models. This presents a significant challenge as we strive to move up the market.The recent change in Stripe's risk behavior has caused us to experience issues with keeping Stripe accounts live.”

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)

Sales tax compliance: nobody in SaaS wants to talk about it. Jon and Justin tried to do something about it and it turned into a nightmare. According to Stripe Tax, there are about 90 different regions that software companies may have to register in, and then calculate, collect, and remit sales tax on their behalf. But in North America, many SaaS companies don't seem to care: many that we looked at weren't collecting sales tax at all, while a few had just started collecting in the US states.If you've been wondering about how sales tax applies to SaaS, listen to this episode.

The whole Transistor team got together for a retreat in Montréal. Jon, Justin, Helen, and Jason chat about the experience. What should we talk about next? Twitter: @buildyoursaas, @mijustin, @jonbuda, @jsonpearl, and @helenrylesLeave a review/comment on Podchaser; it's like Reddit, but for podcasts.Email us: support@transistor.fmThanks to our monthly supporters:Jason CharnesMitchell Davis from RecruitKit.com.auMarcel Fahle, ​​wearebold.afAlex PayneBill CondoAnton Zorin from ProdCamp.comHarris Kenny, Intro CRM podcastOleg KulykEthan GundersonWard Sandler, MemberspaceRussell Brown, Photivo.comNoah PrailColin GrayAustin LovelessMichael SitverPaul Jarvis and Jack Ellis, FathomDan BudaDarby FreyAdam DuVanderDave Giunta (JOOnta)Kyle Fox GetRewardful.comCheck out Simon and Volkan’s new bootstrappers podcast: https://shipsaasfaster.com/ 

As a part of Transistor's 4-year anniversary, Jon and Justin answer your questions

Transistor celebrates 4 years since the launch

An interview with Baptiste Jamin, the co-founder of Crisp. Crisp is affordable, high-quality customer support software.

An interview with Dave Zohrob, co-founder of Chartable podcast analytics

Competing with ChartMogul and Baremetrics, whether you should "go big," and why the market is important

Three French Canadians built a profitable indie SaaS

Becoming a better leader, so that your product can grow and thrive.

"Customer Support may be the most under-appreciated role in SaaS."

We got the whole band together: Helen and Jason join Jon and Justin to talk about what it's really like to work at TransistorHelen, Jason, Jon, Justin, all squeezed into the podcasting closet to make an episode0:55 Jason's first podcast ever1:12 Helen's been on other podcasts: Startups for the Rest of Us, Indie Bites, Indie Worldwide3:06 Should we invest in the "auto publish to YouTube" feature?Tom Webster: why would people listen to podcasts on YouTube?13:32 The best features the ones that feel like "magic" when a customer uses them18:46 The "wait and see" product development philosophy20:15 A new podcast website builder CMS and website designs23:34 Writing a new templating language in Liquid (Shopify)26:23 Our new CLI tool: receiver (built with Go)31:30 Making a few new podcast website themes31:57 Adding language localization for podcast websites (English, French, Spanish)34:30 How we run our weekly team meetings35:44 New podcast website themes are out! (YouTube demo)40:39 For next week: what questions do you have for @jsonpearl and @helenryles?42:16 Patreon shout outsWhat should we talk about next?Twitter: @buildyoursaas, @mijustin, @jonbuda, @jsonpearl, and @helenrylesLeave a review/comment on Podchaser; it's like Reddit, but for podcasts.Email us: support@transistor.fm

Jon and Justin are reunited in the COVID capital of British Columbia

Jon and Justin record one last episode for 2021

Brian talks about why ZipMessage feels different than his other SaaS projects

Justin interviews his daughter about podcast ads, women in podcasting, and how to attract more young listeners.

We answer listener questions about bootstrapping, SaaS, and partnerships