Startups For the Rest of Us

Latest Episodes:

Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions Oct 22, 2024

Show notes

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.

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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: iTunes | Spotify

Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure) Oct 15, 2024

Show notes

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

Episode 734 | The 20 Year Bootstrapper (With Ian Landsman) Oct 08, 2024

Show notes

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

Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure) Oct 01, 2024

Show notes

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

Episode 732 | Lessons Learned Bootstrapping to a $615M Exit Sep 24, 2024

Show notes

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

Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer) Sep 17, 2024

Show notes

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:

For years, they’ve been helping our audience find high quality, global talent at competitive rates, and they can help you too.

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

Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product Sep 10, 2024

Show notes

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

Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies Sep 03, 2024

Show notes

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:

For years, they’ve been helping our audience find high quality, global talent at competitive rates, and they can help you too.

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

Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit Aug 27, 2024

Show notes

In episode 728, Rob Walling interviews Eran Galperin, founder of Gymdesk, about his incredible exit. Eran shares his journey of transforming Gymdesk from "Martial Arts on Rails" into a successful gym management software company. He discusses how they succeeded in a competitive market, the role of TinySeed in their growth, and how feelings of burnout eventually led to a majority buyout for the company.

Topics we cover:

2:02 – Gymdesk Announces a $32.5 Million Strategic Growth Investment
5:13 – How the investment will be used
6:38 – Eran’s projects before Gymdesk
9:21 – Sticking with one idea long enough to see success
12:45 – Entering a competitive market
16:37 – Rapid growth as a marketing leader
20:54 – Dealing with burnout and entertaining an acquisition
26:45 – Handling a stressful sales process
32:19 – The future of Gymdesk

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

Episode 727 | Gymdesk Sells for More than $32.5 million, Hiring Gets Easier, and More Hot Take Tuesday Topics Aug 20, 2024

Show notes

In episode 727, Rob Walling is joined by Tracy Osborn and Einar Vollset to give their hot takes on some recent news. First they celebrate Gymdesk’s recent funding and evaluate what that means for TinySeed companies. Then, they weigh in on bootstrapper hiring, grappling with new challenges as MRR grows, and how to really move the needle in your business.

Episode Sponsor:

For years, they’ve been helping our audience find high quality, global talent at competitive rates, and they can help you too.

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:

2:19 – Gymdesk Announces a $32.5 Million Strategic Growth Investment
9:06 – Is it getting easier for bootstrappers to hire?
12:22 – Facing different challenges as MRR grows
19:37 – Identifying what really moves the needle
23:56 – Listen to those who have built businesses before you

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

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