Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)

In episode 739, Rob Walling interviews Andy Kim, co-founder of Trotto, about his unique journey into SaaS. Andy shares how “go links” work, and why they are so valuable for internal, enterprise use despite their relative obscurity. They also explore the marketing hurdles and customer adoption challenges in a business like Trotto. Episode Sponsor: Hiring senior developers can really move the needle in your business, but if you bring on the wrong person, you can quickly burn through your runway. If you need help finding a vetted, senior, results-oriented developer, you should reach out to today’s sponsor, Lemon.io.  For years, they’ve been helping our audience find high quality, global talent at competitive rates, and they can help you too. Longtime listener Chaz Yoon, hired a senior developer from Lemon.io and said his hire ”definitely knew his stuff, provided appropriate feedback and pushback, and had great communication, including very fluent English. He really exceeded my expectations.”  Chaz said he’d definitely use Lemon.io again when he’s looking for a senior level engineer.  To learn more and get a 15% discount on your first four weeks of working with a developer at lemon.io/startups.  Topics we cover:  3:13 – Go links, URL shorteners for enterprise 6:14 – History of the problem and core users 9:44 – Customer education and growth opportunities 15:37 – Finding the repeatable marketing funnel 21:07 – Buying into a co-founder role at Trotto 24:42 – What’s the hardest part of running Trotto? Links from the Show:  Exit Strategy: The Entrepreneur's Guide to Selling Your Business Without Regret MicroConf Masterminds - Applications close on December 4th, 2024 Trot.to Trotto go links (@TrottoHQ) | X TinySeed How did go links start and evolve at Google? Quiet Light If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you! Subscribe & Review: iTunes | Spotify

In episode 738, join Rob Walling for a solo adventure as he answers listener questions. He explores how to target larger, enterprise deals after achieving product-market fit, and why word of mouth marketing can be great, yet is tricky to control. Rob also answers a later-stage question and cautions against trying to educate the market as a bootstrapper. Topics we cover:  1:58 – Expanding to enterprise deals after product-market fit 6:39 – Word of mouth marketing is tricky for B2B SaaS 14:36 – Educating the market as a bootstrapper 20:07 – Selling integrations through incubators and accelerators 24:38 – Developing a profit sharing model Links from the Show:  Register for MicroConf Remote before Nov. 7th for Early Bird pricing & extras Ask a Question at Startups For the Rest of Us The SaaS Playbook TinySeed Adjacency Matrix: How to expand after PMF by Jason Cohen F5Bot Syften Podscan Veed Devising a profit sharing program for micro-multinationals by Peldi Guilizzoni If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you! Subscribe & Review: iTunes | Spotify

In episode 737, Rob Walling is joined by Derrick Reimer to recap the experience from MicroConf Europe 2024 in Dubrovnik. They discuss the differences between MicroConf US and MicroConf Europe, some small programming tweaks over the years, and they revisit the highlights from the talks at this event.  If you missed the event and had some MicroConf FOMO, get your tickets now for our New Orleans event! Episode Sponsor: Hiring senior developers can really move the needle in your business, but if you bring on the wrong person, you can quickly burn through your runway. If you need help finding a vetted, senior, results-oriented developer, you should reach out to today’s sponsor, Lemon.io.  For years, they’ve been helping our audience find high quality, global talent at competitive rates, and they can help you too. Longtime listener Chaz Yoon, hired a senior developer from Lemon.io and said his hire ”definitely knew his stuff, provided appropriate feedback and pushback, and had great communication, including very fluent English. He really exceeded my expectations.”  Chaz said he’d definitely use Lemon.io again when he’s looking for a senior level engineer.  To learn more and get a 15% discount on your first four weeks of working with a developer at lemon.io/startups.  Topics we cover:  2:47 – MicroConf Europe vs. MicroConf US 6:44 – Adding “excursions” to the programming 11:29 – From Maker to Founder to Owner to Entrepreneur with Peldi Guilizzoni    18:55 – Thinking big and small: Data-driven growth strategies to grow your business with Andrew Davies 20:45 – Contributing factors to the success of this event in particular 23:47 – 10 Lessons Learned in 10 Years of Starting, Growing, and Selling WebinarNinja with Omar Zenhom  26:40 – Bootstrapping Our Freemium Form Builder: From Zero to $1.5M ARR with Marie Martens 30:37 – 3 mistakes I won’t repeat after growing my business to +35M and selling it with Tim Vandecasteele 33:50 – Breaking Through the 7 SaaS Growth Plateaus with Rob Walling Links from the Show:  Get Tickets for MicroConf US 2025, New Orleans Signup for the MicroConf newsletter Derrick Reimer (@derrickreimer) | X SavvyCal Peldi from Balsamiq (@peldi) | X The SaaS Playbook Omar Zenhom (@TheOmarZenhom) | X Episode 717 | Bootstrapping to $1.3M ARR and 300,000 Free Users If you have questions about starting or scaling a software business that you’d like for us to cover, please

In episode 736, join Rob Walling as he answers some later-stage listener questions in another solo adventure. He discusses common pitfalls in delegation, transitioning from one-time transactions to SaaS models, and when it makes sense to target multiple ICPs. Rob also warns about the limited impact that social media marketing can have on growing your SaaS tool. Episode Sponsor: Are you drowning in challenging tech decisions? You should check out today’s sponsor, Techstack.  Unlike typical staffing agencies, these folks are startup specialists with over a decade of experience in startup software development. Techstack can help your startup build an MVP that's designed for explosive growth, rapidly expand your team for new features, or optimize your existing codebase for peak performance. Whether you're launching, scaling up, or fine-tuning, they've got the expertise to supercharge your tech. One of Techstack’s clients was recently featured on Inc. Magazine's Fast Growth Companies list, and they attributed part of their 375% growth to their partnership. Here's an exclusive offer for "Startups For the Rest of Us" listeners: Get a 10% discount on your first month of development with Techstack. And if you're one of the first 10 listeners to get in touch, you'll also receive a free, in-depth tech assessment and expert consultation – a $3,000 value – in your choice of critical areas like architecture, infrastructure, development process or project management. This could be the game-changer your startup needs. Don't let tech challenges slow you down. Check out https://www.tech-stack.com/startups  to discover how Techstack can turbocharge your growth. Topics we cover:  2:17 – What to delegate on the path to $10k MRR 6:43 – Be wary of social media marketing masquerading as productivity 10:31 – DIY vs. hiring a growth agency for B2B SaaS marketing 15:22 – Not every business should be a subscription business 22:00 – Defining, targeting, and selling to different ICPs Links from the Show:  Get Tickets for MicroConf US 2025, New Orleans The SaaS Launchpad TinySeed The Stair Step Method of Bootstrapping Founding Sales by Peter Kazanjy Rob Walling (@robwalling) | X If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you! Subscribe & Review:

In episode 735, join Rob Walling for a solo adventure where he categorizes the different levels of SaaS platform risk. He introduces a framework with three key factors: Replacement, Customer Concentration, and Lead Flow. Rob then defines eight levels of risk according to these factors and other vulnerabilities such as relying on open source – a hot topic with recent news about WordPress, WP Engine, and Automattic.  Episode Sponsor: Hiring senior developers can really move the needle in your business, but if you bring on the wrong person, you can quickly burn through your runway. If you need help finding a vetted, senior, results-oriented developer, you should reach out to today’s sponsor, Lemon.io.  For years, they’ve been helping our audience find high quality, global talent at competitive rates, and they can help you too. Longtime listener Chaz Yoon, hired a senior developer from Lemon.io and said his hire ”definitely knew his stuff, provided appropriate feedback and pushback, and had great communication, including very fluent English. He really exceeded my expectations.”  Chaz said he’d definitely use Lemon.io again when he’s looking for a senior level engineer.  To learn more and get a 15% discount on your first four weeks of working with a developer at lemon.io/startups.  Topics we cover:  2:32 – Are replacements available for this platform? 4:56 – How concentrated are your customers on this platform? 5:31 – What is your lead or customer flow? 8:54 – Level 1: almost no platform risk 10:04 – Level 2: reliant on a commoditized platform 11:49 – Level 3: using large cloud providers like AWS 15:33 – Level 4: deeply tied to open source software like WordPress 18:11 – Level 5: high switching costs, but replacements exist like in no-code 20:00 – Level 6: 100% lead flow risk 21:44 – Level 7: a friendly app ecosystem 23:24 – Level 8: aggressive platforms, few replacements, customer concentration Links from the Show:  Get Tickets for MicroConf US 2025, New Orleans TinySeed Rob Walling (@robwalling) | X Ask a Question on SFTROU How to find and validate business ideas from 75+ SaaS Marketplaces If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you! Subscribe & Review: iTunes | Spotify

In episode 734, Rob Walling interviews Ian Landsman, founder of HelpSpot, about his 20-year bootstrapper journey. They discuss Ian's transition from on-prem software to SaaS, the challenges and benefits of each, and the early days of building the business. They wrap up by discussing the potential impact of AI on the customer service industry.  Topics we cover:  1:11 – Ian, the OG bootstrapper 2:22 – Benefits of on-prem software in 2024 5:46 – Slow, steady, profitable growth through the years 9:20 – Embracing a risky start 14:11 – Getting early awareness 18:52 – Transitioning to SaaS 26:37 – Laravel raises $57M 28:59 – AI impact on customer service Links from the Show:  The SaaS Playbook TinySeed Ian Landsman (@ianlandsman) | X HelpSpot (@helpspot) | X HelpSpot Podscan Accel invests $57M into Laravel Products & Open-Source Framework Mostly Technical If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you! Subscribe & Review: iTunes | Spotify

In episode 733, join Rob Walling for a solo adventure where he covers several topics. In this episode he differentiates between good and bad distractions, weaknesses versus blind spots, and shares personal experiences of struggle. He concludes with actionable advice – uncover the blind spots, then launch, iterate, and take feedback. Topics we cover:  2:09 – Not all distractions are bad 5:42 – The worst distractions masquerade as productivity 9:48 – Weaknesses versus blind spots 16:41 – Everybody struggles  24:40 – Launch, iterate, and take feedback Links from the Show:  The SaaS Launchpad The SaaS Playbook MicroConf Connect The Hard Thing About Hard Things by Ben Horowitz Why Startup Founders Should Stop Reading Business Books by Rob Walling Traction by Gabriel Weinberg, Justin Mares Episode 725 | SEO in the Age of AI, Freemium, When Brand Becomes Important, and More Advanced Listener Questions (with Ruben Gamez) Launch. A Startup Documentary. If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you! Subscribe & Review: iTunes | Spotify

In episode 732, Rob Walling interviews Jeff, a mostly anonymous and retired founder, about his mostly bootstrapped business and subsequent exits. Jeff shares how he started the company in 2003 and how he persevered in the early, lonely years to achieve traction in the business. They also discuss finding fulfillment after a huge, life-changing exit. Topics we cover:  2:17 – Jeff, the retired SaaS founder you haven’t heard of 3:32 – Refreshing the bank balance after multiple exits 5:26 – ARR multiples across several exits 8:11 – “Accidentally” SaaS, growing the business in the early days 11:35 – Getting through the toughest moments in the journey 16:31 – Why did the business work? 20:14 – “Short term generous, long term greedy” 24:32 – Staying busy after an exit 32:09 – Giving back to founders Links from the Show:  Purchase The SaaS Launchpad before September 30th to get access to a live Q&A with Rob TinySeed Retired Founder (@RetiredFounder) | X Contact Retired Founder Beyond The Finish Line If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you! Subscribe & Review: iTunes | Spotify

In episode 731, join Rob Walling and Derrick Reimer as they tackle some more advanced listener questions. They discuss delegation and giving up areas of control as a founder, including examples from their time together at Drip. Derrick describes how he approaches partnering with other SaaS businesses and why planning a full quarter ahead doesn’t work for many bootstrapped founders. Episode Sponsor: Hiring senior developers can really move the needle in your business, but if you bring on the wrong person, you can quickly burn through your runway. If you need help finding a vetted, senior, results-oriented developer, you should reach out to today’s sponsor, Lemon.io.  For years, they’ve been helping our audience find high quality, global talent at competitive rates, and they can help you too. Longtime listener Chaz Yoon, hired a senior developer from Lemon.io and said his hire ”definitely knew his stuff, provided appropriate feedback and pushback, and had great communication, including very fluent English. He really exceeded my expectations.”  Chaz said he’d definitely use Lemon.io again when he’s looking for a senior level engineer.  To learn more and get a 15% discount on your first four weeks of working with a developer at lemon.io/startups.  Topics we cover:  1:17 – Delegating as a perfectionist 7:19 – Learning to hire those that are better than you in some domains 14:50 – Risk vs. certainty 19:01 – Finding specialized marketing roles vs. a generalist 24:04 – Managing partnerships with other SaaS products 31:17 – Reaching out about partnerships 32:46 – Quarterly planning for your SaaS 34:20 – Planning in smaller time blocks 40:58 – Quizzing developers’ on their knowledge Links from the Show:  Purchase The SaaS Launchpad TinySeed The SaaS Playbook MicroConf YouTube Channel Derrick Reimer (@derrickreimer) | X SavvyCal Finding Fulfillment by Jason Cohen Shape Up If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you! Subscribe & Review: iTunes | Spotify

In episode 730, Craig Hewitt turns the table and interviews Rob Walling about releasing The SaaS Launchpad course. Craig, founder of Castos, asks Rob about the course's purpose and structure, which founders that it’s designed for, and why he made a course as opposed to a new book, or a YouTube series. They also discuss the pricing strategy, hosting platforms, accountability, community, and more. If you’re trying to take your SaaS from zero to one, purchase The SaaS Launchpad before September 30th to get access to a live Q&A with Rob. Topics we cover:  2:00 – Why a course? 4:35 – Who is it for? 9:37 – Breaking down the pricing behind the course 14:32 – Choosing a platform to host the course 17:47 – Enabling action from those who enroll 27:33 – Course topics that help founders get early traction 30:26 – The biggest problems early-stage founders face Links from the Show:  The SaaS Launchpad Craig Hewitt (@TheCraigHewitt) | X Castos The Rouge Startups podcast Craig’s YouTube Channel Episode 606 | The Podcasting Landscape, Keeping Your Saw Sharpened, and Scaling Your Team with Craig Hewitt The SaaS Playbook MicroConf Connect MicroConf Mastermind Matching The MicroConf YouTube channel TinySeed Episode 726 | Selling 29,000 Copies, Information vs. Motivation, and Making Your First Level Last (A Rob Solo Adventure) Circle.so Ruben Gamez (@earthlingworks) | X Lianna Patch (@punchlinecopy) | X Derrick Reimer (@derrickreimer) | X Ross Hudgens (@RossHudgens) | X Episode 628 | The 5 PM Pre-Validation Framework If you have questions about starting or scaling a software busines...