Rob Walling

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Rob Walling
Rob Walling.jpg
Occupationserial entrepreneur, author, podcaster

Rob Walling is a serial entrepreneur, author, podcaster,[1] and angel investor.[2] He is the author of Start Small, Stay Small: A Developer's Guide to Launching a Startup, which was published in 2010.[3][4]

Walling is the founder of email marketing software Drip[5][6] that was acquired in a life-changing exit[7] by Leadpages in July 2016.[8]


In the early 2000s Walling tried to launch a number of software products that failed. He had his first notable success with DotNetInvoice, an invoicing software application. Subsequently, he launched other small business and formed an online community of software founders called Micropreneurs.[9]

In 2010 he started a podcast with Mike Taber, which became one of the most popular startup podcasts in iTunes, called Startups for the Rest of Us.[10] The next year, in June, he co-founded MicroConf,[11] a conference for self-funded startups,[12] which is held twice a year in Las Vegas and Europe.[13]

In August 2011 Walling purchased and revamped HitTail, a web-based software as a service product that provides long tail keyword suggestions.[14] Before purchasing HitTail, it had used a freemium business model to market the product.[15] Walling stopped the freemium model and used traditional software marketing to bring in more paying users.[16] He founded Drip, an email marketing tool that allows a user to send emails to their audience based on user behavior, in 2012.[17]

Walling has become known as a supporter of self-funding or bootstrapping software companies that turn a profit, instead of raising funding from venture capitalists.[10][18] Much of his writing focuses on tactics for growing software as a service startups.[19][20]

In 2014, he wrote the foreword to Dan Norris' book, The 7-Day Startup: You Don't Learn Until You Launch.[21]

In March 2015 Walling published one of his best-known essays titled The Stairstep Approach to Bootstrapping[22] where he outlines a potentially safer, more structured approach to bootstrapping a startup by starting with small, simple product ideas and leveraging the revenue and experience earned from them to tackle more ambitious (and typically more financially rewarding) ideas.

This approach was the focus of a chapter of the 2015 book The End of Jobs: Money, Meaning and Freedom Without the 9-to-5 by Taylor Pearson.[23]

On July 26, 2016, his company, Drip, was acquired by Leadpages for an undisclosed amount. He led the Drip product team, out of Leadpages’ Minneapolis headquarters, until April 2018.[24]

In October 2018, Walling announced that he was starting the first startup accelerator designed for bootstrappers, called TinySeed.[25]


  1. ^ "How to Identify a Wannabe Thought Leader". Mashable. May 20, 2013.
  2. ^ "Rob Walling".
  3. ^ Walling, Rob (2010). Start Small, Stay Small. ISBN 9780615373966.
  4. ^ "Home".
  5. ^ "About".
  6. ^ "The Hottest Currency On The Internet (That You Probably Aren't Investing In)". Forbes.
  7. ^ "How Drip started as a widget and was acquired by Leadpages for a life-changing sum". Mixergy.
  8. ^ "Announcement: Leadpages Has Acquired Drip". July 7, 2016.
  9. ^ "Learn from Proven Entrepreneurs". Mixergy.
  10. ^ a b "12 Best Online Courses for Learning Practical Business Skills". The Huffington Post. April 9, 2014.
  11. ^ "How Rob Walling Created a Thriving SaaS Community with MicroConf". SaaSMag. August 6, 2020.
  12. ^ "Bootstrapped startups buck trend toward VC bucks". San Francisco Chronicle. August 9, 2015.
  13. ^ Jon Russell (December 15, 2013). "7 'digital nomads' explain how they live, work and travel". The Next Web.
  14. ^ "Learn from Proven Entrepreneurs". Mixergy.
  15. ^ "Web, quando la strategia Freemium si rivela un flop". August 23, 2012.
  16. ^ Sarah E. Needleman and Angus Loten (August 22, 2012). "When Freemium Fails". WSJ.
  17. ^ "Why Marketing Automation Tools Are the Future of Email Marketing for Business". Huffington Post. October 13, 2015.
  18. ^ "How to Make Six Figures, Part 5". July 19, 2010.
  19. ^ "5 Steps to Reduce Your Churn Rate". Business 2 Community. January 26, 2014.
  20. ^ TJ McCue (April 4, 2012). "$14 Billion Software as a Service Industry Growth Influences Maker Companies". Forbes.
  21. ^ Norris, Dan (September 29, 2014). The 7 Day Startup. ISBN 9781502472397.
  22. ^ "The Stairstep Approach to Bootstrapping".
  23. ^ The End of Jobs.
  24. ^ "Leadpages Acquires CA Marketing Automation Company Drip – TECHdotMN". TECHdotMN. July 7, 2016. Retrieved March 15, 2018.
  25. ^ "My Next Act: Building The First Startup Accelerator Designed for Bootstrappers".

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