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Startups For the Rest of Us

Rob Walling

The most popular podcast for bootstrapped and mostly bootstrapped startup founders

  • 29 minutes 38 seconds
    Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem

    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: 

    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

    12 November 2024, 10:00 am
  • 28 minutes 40 seconds
    Episode 738 | Encouraging Word of Mouth, Educating a Market, and More Listener Questions (A Rob Solo Adventure)

    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: 

    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

    5 November 2024, 10:00 am
  • 42 minutes 11 seconds
    Episode 737 | Key Takeaways from MicroConf Europe 2024 (With Derrick Reimer)

    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: 

    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

    29 October 2024, 10:00 am
  • 27 minutes 49 seconds
    Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions

    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: 

    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

    22 October 2024, 10:00 am
  • 26 minutes 58 seconds
    Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)

    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: 

    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

    15 October 2024, 10:00 am
  • 35 minutes 3 seconds
    Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)

    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: 

    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

    8 October 2024, 10:00 am
  • 27 minutes 19 seconds
    Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)

    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: 

    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

    1 October 2024, 10:00 am
  • 36 minutes 25 seconds
    Episode 732 | Lessons Learned Bootstrapping to a $615M Exit

    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: 

    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

    24 September 2024, 10:00 am
  • 49 minutes 5 seconds
    Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)

    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: 

    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

    17 September 2024, 10:00 am
  • 37 minutes 31 seconds
    Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product

    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: 

    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

    10 September 2024, 10:00 am
  • 25 minutes 27 seconds
    Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies

    In episode 729, join Rob Walling as he shares insights from the 170+ SaaS investments he’s made through his B2B SaaS accelerator, TinySeed. Key patterns include the survivability of SaaS, the lucrative value of these companies, and commonalities across the ones that grow the fastest. To see even more patterns that didn’t make this episode, be sure to check out the MicroConf YouTube channel.

    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: 

    • 2:24 – Survivability of B2B SaaS in TinySeed
    • 4:09 – SaaS is extremely valuable
    • 8:26 – Vertical and orthogonal SaaS face fewer headwinds 
    • 12:36 – A supermajority of TinySeed companies want a big exit
    • 15:51 – TinySeed founder count aligns with the broader MicroConf ecosystem
    • 17:04 – Ruined cap tables have prevented deals
    • 19:35 – A quarter of TinySeed companies raise subsequent fundraising
    • 21:17 – Common advisory topics: pricing, plateaus, cofounders, funding, selling

    Links from the Show: 

    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

    3 September 2024, 10:00 am
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