• Episode 745 | Reflecting on 2024: Revisiting My Predictions, The Best Episodes, My Favorite Frameworks, and More (A Rob Solo Adventure)
    Dec 24 2024

    In episode 745, Rob Walling goes solo to reflect on 2024. He revisits key concepts and frameworks introduced on the podcast, including the 2-20-200 Validation Framework, Orthogonal SaaS, and the eight levels of platform risk. Rob also looks back at his top five favorite episodes and reviews his predictions for the year—some of which came to pass, and others that didn’t.

    Topics we cover:
    • (2:05) – Looking back at concepts and frameworks from past 12 months
    • (8:50) – Rob’s 5 favorite episodes
    • (11:56) – Reflecting on 2024 accomplishments
    • (19:47) – TinySeed Tales Returns in 2025
    • (21:18) – Evaluating 2024 predictions
    Links from the Show:
    • The SaaS Launchpad – Start Free with “The DNA of a Great SaaS Idea”
    • MicroConf YouTube Channel
    • Episode 706 | 2/20/200 Validation, Prior Art, and Designing by Committee (A Rob Solo Adventure)
    • TinySeed
    • Vertical SaaS vs Horizontal SaaS - Which is More Profitable?
    • Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
    • The SaaS Playbook
    • Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit
    • Episode 706.5 | Rethinking My Most Common Advice
    • Episode 729 | 9 Things I’ve Learned Investing in 170+ SaaS Companies
    • Episode 709 | The 7 Greatest Investments of My Life
    • Episode 694 | 2023 In Review: Amazing Growth & Fighting Burnout
    • How Ben Chestnut Bootstrapped Mailchimp to a $12 Billion Exit
    • MicroConf New Orleans 2025
    • Start Small, Stay Small by Rob Walling
    • Exit Strategy: The Entrepreneur's Guide to Selling Your Business Without Regret
    • TinySeed Tales
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    27 mins
  • Episode 744 | Bluesky, TinySeed is Raising, YC Backs Competitors, and More Hot Take Tuesday Topics
    Dec 17 2024

    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:
    • The SaaS Launchpad – Start Free with “The DNA of a Great SaaS Idea”
    • Invest in TinySeed
    • Rob Walling (@robwalling.com) | Bluesky
    • TinySeed (@tinyseed.com) | Bluesky
    • Tracy Osborn (tracymakes) (@tracyosborn.com) | Bluesky
    • Einar Vollset (@einarvollset) | X
    • Y Combinator often backs startups that duplicate other YC companies, data shows
    • Procrastination and the Fear of Not Being 'Good Enough' by Swapnil Chauhan
    • Startup Founders, Do THIS to Beat Imposter Syndrome
    • Australia proposes 'world-leading' ban on social media for children under 16

    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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    34 mins
  • Episode 743 | How to Sell Your Business Without Regret
    Dec 10 2024

    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:
    • Exit Strategy: The Entrepreneur's Guide to Selling Your Business Without Regret
    • Back the book on Kickstarter
    • MicroConf Connect Applications Close Today, December 10th
    • Rob Walling (@robwalling) | X
    • Dr. Sherry Walling (@sherrywalling) | X
    • The SaaS Playbook
    • Built to Sell by John Warrillow
    • Touching Two Worlds by Dr. Sherry Walling
    • The Entrepreneur’s Guide to Keeping Your Sh*t Together by Sherry Walling, PhD, Rob Walling

    If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your quest...

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    37 mins
  • Episode 742 | Normalizing Hard Things, Facing Your Biggest Threat, and Making it Fast (A Rob Solo Adventure)
    Dec 3 2024

    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:
    • Exit Strategy: The Entrepreneur's Guide to Selling Your Business Without Regret
    • MicroConf Masterminds Applications Close on December 4th
    • Rob Walling (@robwalling) | X
    • Dr. Sherry Walling (@sherrywalling) | X
    • The Comic Lab Podcast
    • The SaaS Playbook
    • The Stair Step Method of Bootstrapping
    • This Took 11 Years to Be An "Overnight Success" - SaaS Exit Strategy

    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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    28 mins
  • Episode 741 | What Actually is Product Led Growth? (with Wes Bush)
    Nov 26 2024

    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:
    • Mastermind Applications are open until December 4th
    • Wes Bush (@wes_bush) | X
    • ProductLed (@productled) | X
    • ProductLed
    • Product-Led Growth: How to Build a Product That Sells Itself by Wes Bush
    • The Product-Led Playbook: How to Unlock Self-Serve Revenue and Dominate Your Market (With a Tiny Team) by Wes Bush
    • Free Audiobook of The Product-Led Playbook
    • Product-Led Onboarding by Ramli John
    • TinySeed
    • SparkToro
    • SavvyCal

    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!

    ...
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    32 mins
  • Episode 740 | My New Book! The Entrepreneur's Guide to Selling Your Business Without Regret
    Nov 19 2024

    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:
    • MicroConf Remote Goes Live November 20th!
    • Exit Strategy: The Entrepreneur's Guide to Selling Your Business Without Regret
    • Rob Walling (@robwalling) | X
    • Dr. Sherry Walling (@sherrywalling) | X
    • Zen Founder
    • Zen Founder Podcast
    • The SaaS Playbook
    • The Art of Selling Your Business by John Warrillow
    • Before the Exit by Dan Andrews
    • Finish Big by Bo Burlingham
    • MicroConf
    • TinySeed
    • Touching Two Worlds by Dr. Sherry Walling

    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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    30 mins
  • Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem
    Nov 12 2024

    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

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    30 mins
  • Episode 738 | Encouraging Word of Mouth, Educating a Market, and More Listener Questions (A Rob Solo Adventure)
    Nov 5 2024

    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

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    29 mins