From Bootstrap Startup to an 8-Figure Exit with Rob Walling

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Today, another serial entrepreneur, Rob Walling, joins us to discuss founding and generally running a bootstrap startup. We sat down and talked to Rob about his journey of getting his software startup off the ground, developed, and eventually sold with no outside funding.

Rob Walling is not only the co-founder of Drip, which recently sold for eight figures, he also writes a blog and hosts two podcasts for startups. He is most known for starting, running and selling Drip but he has also bought and sold several smaller SaaS applications, including HitTail. Finally, Rob is co-founder of Microconf, a bi-annual conference for software startups. Rob’s goal is to continue to acquire new businesses while maintaining the time-clock free lifestyle his years of software startup and acquisition experience have afforded him.

Episode Highlights:

  • The story behind Drip and what led Rob into marketing automation.
  • Building and growing a SaaS company. Launching a new software business without a lot of staff or cash.
  • Building the automation that ended up being the key factor that got Drip on the consumer radar.
  • How the company managed to compete against the larger players.
  • The luxury of being a small team and working primarily in person.
  • Why Rob would now choose remote over local.
  • Tips for hiring high quality candidates that fit in with your company’s principles.
  • When you know it is time to scale up your startup. Knowing when you have something that people really want.
  • How to recognize when the option to sell comes on the radar.
  • Knowing when you’ve found the right buyer.
  • The importance of putting all the deal-breakers on the table and sticking to your guns.
  • What small startups learn in the acquisition and transition process and how that changes their teams.
  • The story behind Microconf, Rob’s bi-annual global software conference unlike any other.

Transcription:

Joe: So this morning we were deep into a program called GetDrip and it’s what we use for our automated email sequences. And I understand you had the founder of that gentleman … with that software as a service program on the podcast that’s all right?

Mark: That’s right and I think a lot of our listeners are probably familiar with Rob Walling. He writes over at Software by Rob. He is the host over at Start Ups for the Rest of Us Podcast. He’s the founder or co-founder I should say of MicroConf the SaaS conference. He is also the founder of HitTail an SEO software and of course Drip – Email Marketing Automation; one of the leading email marketing automation softwares out there which was acquired by Leadpages a few years ago in an eight figure acquisition. So really cool guy, tons of experience in a lot of different areas especially in that start up environment. And Joe you and I like to have these calls with people … these conversations with people where we try and like pull out a certain lesson or something else. Remember the episode with Mike Jackness and the crazy high open rates and returns that he gets on his Facebook marketing. I went into this without any specific agenda. I just want to talk to Rob about his story and kind of the adventure he’s been on since he started up Drip and some of the other things as well. But we didn’t get into much else because we just kind of talked about his journey with Drip which was fascinating. And one of the things to think about with Drip, they started off in a world where there was really big competitors. You had Infusionsoft, you had Klaviyo that was still big at the time, you had MailChimp which was absolutely a monster, AWeber which had been around forever. And here you have this little start up with no funding just a handful of coders working out of basically a clos

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