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Startups For the Rest of Us

Rob Walling

The most popular podcast for bootstrapped and mostly bootstrapped startup founders

  • 33 minutes 57 seconds
    Episode 744 | Bluesky, TinySeed is Raising, YC Backs Competitors, and More Hot Take Tuesday Topics

    In episode 744, Rob Walling is joined by Tracy Osborn and Einar Vollset to give their hot takes on some recent news. They cover the recent rise of Bluesky, kicking off a 4-figure bet between Tracy and Einar. Then they discuss TinySeed’s third fund, YC Combinator backing competitors, dealing with imposter syndrome, and finally government involvement in banning social media.

    Topics we cover: 

    • (1:49) – Will Bluesky survive and thrive?
    • (9:07) – The bet on Bluesky growth
    • (13:46) – TinySeed is raising a third fund
    • (17:25) – Y Combinator backs duplicates
    • (22:18) – Dealing with Imposter Syndrome
    • (27:46) – Australia's social media ban

    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 December 2024, 10:00 am
  • 36 minutes 42 seconds
    Episode 743 | How to Sell Your Business Without Regret

    In episode 743, Rob Walling and Dr. Sherry Walling read the first chapter of their new book, Exit Strategy: The Entrepreneur’s Guide to Selling Your Company Without Regret. They discuss the emotional and psychological challenges of selling a business, and why it’s often harder than founders expect. They offer insights on how to prepare for a sale, protect your mental health, and how to best navigate this major life change that few others understand.

    Back the book on Kickstarter

    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: 

    • (1:49) – Exit Strategy Introduction
    • (6:56) – Exits are complicated
    • (11:16) – One of the hardest things you’ll ever do
    • (15:57) – Your business is your baby 
    • (18:35) – Entering the unknown
    • (26:49) – Six factors that shape how you feel about an exit
    • (31:03) – Making it real

    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 December 2024, 10:00 am
  • 28 minutes 21 seconds
    Episode 742 | Normalizing Hard Things, Facing Your Biggest Threat, and Making it Fast (A Rob Solo Adventure)

    In episode 742, Rob Walling goes solo to explore normalizing doing hard things and facing your biggest threats. He also discusses a framework for founders looking to scale without cutting corners – making things work, making them right, and then making them fast.

    Exit Strategy Kickstarter ends on December 12!

    Topics we cover: 

    • (2:39) – Normalizing doing hard things
    • (6:54) – The “hard things” in your startup
    • (10:27) – Walking into the storm
    • (16:21) – ”Make it work, make it right, make it fast”
    • (22:04) – Building your “Founder Gut”
    • (25:42) – Think in years, not months

    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 December 2024, 10:00 am
  • 31 minutes 48 seconds
    Episode 741 | What Actually is Product Led Growth? (with Wes Bush)

    In episode 741, Rob Walling talks to Wes Bush, CEO and Founder of ProductLed, about the nuances and misconceptions of product-led growth. Wes debunks common myths and explains how companies can leverage their product to drive user acquisition, engagement, and growth. They dive into a real-world example and explore how founders can avoid the trap of thinking the product will “sell itself” while contrasting PLG and sales-led strategies.

    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: 

    • (2:01) – Defining product-led growth
    • (6:07) – Are users able to get value for free? 
    • (11:38) – Hybrid: both product-led and sales-led
    • (14:52) – Determining the main outcome of your free model
    • (19:23) – Misuse of the PLG terminology
    • (22:00) – The benefits of PLG over sales-led growth
    • (24:08) – Workshopping SavvyCal’s product-led strategy

    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

    26 November 2024, 10:00 am
  • 29 minutes 49 seconds
    Episode 740 | My New Book! The Entrepreneur's Guide to Selling Your Business Without Regret

    In episode 740, Rob Walling speaks with Dr. Sherry Walling about their new book, "Exit Strategy: The Entrepreneur's Guide to Selling Your Business Without Regret." They explore the emotional, psychological, and practical aspects of selling a business, emphasizing the universal challenges entrepreneurs face. The book draws on both Rob and Sherry’s unique experiences that they’ve shared with countless founders throughout their careers.

    Exit Strategy is now live on Kickstarter!

    Topics we cover: 

    • 2:01 – Not just a book for those selling SaaS
    • 8:13 – The Kickstarter for the book is live today
    • 12:16 – Before, during, and after the exit
    • 14:55 – Why exiting is so hard
    • 20:39 – Life after the exit
    • 25:10 – A few traps await founders shortly after exit
    • 26:24 – What do you do with a big pile of money?

    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

    19 November 2024, 10:00 am
  • 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
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