The Bootstrapped Founder

270: Rob Walling — Stair-Stepping into SaaS Success


Listen Later

Rob Walling (@robwalling) unpacks the fascinating world of SaaS businesses, touching on topics like scaling, diversification, and the role of AI in SaaS projects. Rob shares his unique stair-step approach to building a SaaS business and paints a realistic picture of the challenges faced by a SaaS founder and the potential rewards of running a successful SaaS company.

The man has released almost 700 podcast episodes about bootstrapping SaaS businesses. He knows how that works, from the birds-eye perspective down to the nitty gritty.

We dive into the misconception around building a ChatGPT wrapper as a long-term business, the trend of AI-centric startups using one-time payments or yearly subscriptions, and the risk of overindexing on AI as a competitive advantage. We also examine common pitfalls in the software business and the impact of sales models on customers. Rob offers insights on white labeling, cautioning against doing it too early and advising on setting a minimum commitment from potential partners.

Rob shares his personal experiences, discussing the difficulties of setting investment terms and overcoming setbacks. We address the concept of the "solo founder funk" and offer solutions such as finding a co-founder, joining mastermind groups, and attending in-person events. Lastly, we delve into the importance of building an audience in the world of SaaS and discuss the topic of hiring in early-stage startups. So tune in, learn, and get inspired by Rob's journey and insights in the SaaS industry.

Rob Walling on Twitter: https://twitter.com/robwalling

00:00:00 Scaling SaaS Businesses With Diversification
00:12:56 Building on AI and Subscription Fatigue
00:21:58 Sales Model and Customer Requests
00:33:29 Founder Strategies
00:40:10 Building an Audience in SaaS Marketing
00:46:11 Founders Discuss Hiring and Growth


This episode is sponsored by Acquire.com


The blog post: https://thebootstrappedfounder.com/rob-walling-stair-stepping-into-saas-success/

The podcast episode: https://tbf.fm/episodes/270-rob-walling-stair-stepping-into-saas-success

The video: https://youtu.be/GjmvLv-4YtY

You'll find my weekly article on my blog: https://thebootstrappedfounder.com

Podcast: https://thebootstrappedfounder.com/podcast

Newsletter: https://thebootstrappedfounder.com/newsletter


My book Zero to Sold: https://zerotosold.com/

My book The Embedded Entrepreneur: https://embeddedentrepreneur.com/

My course Find Your Following: https://findyourfollowing.com

Here are a few tools I use. Using my affiliate links will support my work at no additional cost to you.
- Notion (which I use to organize, write, coordinate, and archive my podcast + newsletter): https://affiliate.notion.so/465mv1536drx
- Riverside.fm (that's what I recorded this episode with): https://riverside.fm/?via=arvid
- TweetHunter (for speedy scheduling and writing Tweets): http://tweethunter.io/?via=arvid
- HypeFury (for massive Twitter analytics and scheduling): https://hypefury.com/?via=arvid60
- AudioPen (for taking voice notes and getting amazing summaries): https://audiopen.ai/?aff=PXErZ
- Descript (for word-based video editing, subtitles, and clips): https://www.descript.com/?lmref=3cf39Q
- ConvertKit (for email lists, newsletters, even finding sponsors): https://convertkit.com?lmref=bN9CZw


  • (00:00) - Scaling SaaS Businesses With Diversification
  • (12:56) - Building on AI and Subscription Fatigue
  • (21:58) - Sales Model and Customer Requests
  • (33:29) - Founder Strategies
  • (40:10) - Building an Audience in SaaS Marketing
  • (46:11) - Founders Discuss Hiring and Growth
  • ...more
    View all episodesView all episodes
    Download on the App Store

    The Bootstrapped FounderBy Arvid Kahl

    • 5
    • 5
    • 5
    • 5
    • 5

    5

    32 ratings


    More shows like The Bootstrapped Founder

    View all
    The Official SaaStr Podcast: SaaS | Founders | Investors by SaaStr

    The Official SaaStr Podcast: SaaS | Founders | Investors

    172 Listeners

    The Changelog: Software Development, Open Source by Changelog Media

    The Changelog: Software Development, Open Source

    291 Listeners

    Startups For the Rest of Us by Rob Walling

    Startups For the Rest of Us

    697 Listeners

    Software Engineering Daily by Software Engineering Daily

    Software Engineering Daily

    624 Listeners

    Built to Sell Radio by John Warrillow

    Built to Sell Radio

    209 Listeners

    Noah Kagan Presents by Noah Kagan

    Noah Kagan Presents

    902 Listeners

    Y Combinator Startup Podcast by Y Combinator

    Y Combinator Startup Podcast

    232 Listeners

    Syntax - Tasty Web Development Treats by Wes Bos & Scott Tolinski - Full Stack JavaScript Web Developers

    Syntax - Tasty Web Development Treats

    987 Listeners

    REWORK by 37signals

    REWORK

    210 Listeners

    My First Million by Hubspot Media

    My First Million

    2,643 Listeners

    The Startup Ideas Podcast by Greg Isenberg

    The Startup Ideas Podcast

    202 Listeners

    Latent Space: The AI Engineer Podcast by swyx + Alessio

    Latent Space: The AI Engineer Podcast

    96 Listeners

    Moneywise by Hampton

    Moneywise

    652 Listeners

    AI + a16z by a16z

    AI + a16z

    33 Listeners

    Lightcone Podcast by Y Combinator

    Lightcone Podcast

    22 Listeners