Save Thousands in Churn and Increase Retention W/ Travis Steffen

Jason Kirby (00:00.223): interesting tidbits that might come up before we actually kind of make it an official live and they just chop it up and make work. Is there anything you, well guess we just went live, but anything you don't want to talk about?

Travis Steffen (00:07.288): sensible.

Travis Steffen (00:13.006): There are I mean there might be one or two exits right where I probably won't talk about a dollar figure but Most details are fine. You know, I'd say I'm happy to talk about the Growflow one as well and There might be a couple details of what went down like after the fact after the exit was done That impacted kind of like people what people got paid. I might not reveal all those But but I'm happy to talk about a little bit

Jason Kirby (00:41.253): Yeah, don't need to be putting yourself on the chopping block with partners or any of kind of stuff. But when it comes to the companies, because there's a lot and it's actually, it was really hard for me to like actually break down all the companies you've sold. But in a capacity of like your role, like were you founder CEO of all those eight companies or were you like,

Travis Steffen (00:45.56): Sure.

Travis Steffen (00:56.398): Sure.

Travis Steffen (01:03.918): Yeah. Any of the ones I'm counting in the eight, I was either a founder or co-founder and or CEO. There are a couple in there that I was just CEO, not a founder. Like I was brought in for a turnaround or something like that. That's maybe 20% of the time. I've only done maybe like three turnarounds counting one that I'm doing right now. And they're fine. They're like their own fun puzzle, but

Travis Steffen (01:03.918): You know, honestly, those are often a lot harder than the ones that I start because you have to clean up a lot of bad things. So or things that were done incorrectly or people that were upset that are investors or stakeholders in some way. And but, you know, so there are a number of others where I've like, you know, helped someone get through exit or I've contributed in some meaningful way that would not be counted in that figure.

Jason Kirby (02:01.285): So we're going to be talking a lot about, you know, churn and the churn of, and how that impacts business. think if are there any stats you can kind of speak to in terms of the scale of your exits, like all transactions totaling whatever X or all your aggregate revenue generated X like some kind of like high level stat that we can.

Travis Steffen (02:20.308): Yeah, let's see. Raised over 100 million in my career across several companies. About half my exits have been bootstrapped, I'd say. Stats-wise, Growflow exit was just shy of 70 million. Let's see. Collectively in the aggregate, probably we're looking at somewhere in the neighborhood of

Travis Steffen (02:58.659): It depends on if we count one that I kind of like was the core operator of that we took public for 526 million. I tend not to count that just because I wasn't the founder. Yeah, that's that's I was a you know, IPO via SPAC, but that's that's kind of one that I don't often talk about just because the founders did eventually long after I was gone, you know, lie to investors pretty publicly and then got

Jason Kirby (03:14.892): That's big one. That's not like.

Travis Steffen (03:31.598): I would say if we don't count lottery.com, we're probably looking at somewhere around 200 or so, maybe just shy of 200. The first probably four or five exits that I had in my career were kind of like the mild to moderate ones, but they were all bootstrapped. So they were actually better outcomes for me in comparison to some of the ones that were venture backed where we had a press stack that we had to clear.

Jason Kirby (07:39.461): And we'll talk about prep stacks potentially as well. But now as far as kicking this off, so basically I'll introduce you, Travis Steffen, founder and CEO of Rivalto, serial exit of founder with eight exits, raised over a hundred million and has 200 million in exits. Welcome to the show. We're going to talk about how businesses can stop churn and increase material impact.

Travis Steffen (07:40.856): Yeah. Awesome.

Jason Kirby (08:09.445): Everyone, welcome back to Fundraising Demystified. Today, I'm excited to have Travis Steffen on the show. A serial founder to the point of eight exits has raised over $100 million and has transacted an M&A over $200 million. Travis, you have an incredible track record.

Travis Steffen (08:05.922): Awesome.

Jason Kirby (09:25.546): You're currently running Rivalto to help founders reduce churn. Welcome to the show.

Travis Steffen (09:31.192): Thank you for having me. Super excited to kick this off.

Jason Kirby (09:33.647): You're a very modest man, you know, with eight exits behind you. I always like to think that my four exits completely humbled by your track record. I think it would be great for people to understand what makes you tick—why you’re a nonstop builder.

Travis Steffen (09:52.44): It's a compulsion. I thrive in multiplayer games—co-founder environments. I love puzzles; startups are the ultimate wet spaghetti puzzle. I systemize to free time, then build again—about one new thing a year, shutting down fast failures.

Jason Kirby (12:58.719): Founders often cling to tired “never quit” advice. But you need clear success/failure boundaries or you burn years bailing water in a leaking boat.

Travis Steffen (13:20.396): Exactly—assign constraints and definitions early. Ruthlessly kill experiments—Zuckerberg style—to avoid founder burnout.

Jason Kirby (13:57.123): Let’s talk the silent killer: churn. Define it.

Travis Steffen (17:35.438): Churn ≠ just cancellations. Voluntary vs involuntary. It’s your inflow/outflow velocity; hit carrying capacity when acquisition = churn. Leading indicator = engagement. Cohort analysis is crucial. 10× more content on acquisition than retention; retention is cheaper and more important.

Jason Kirby (22:38.021): 10% monthly churn = insane annual loss—often at carrying capacity.

Travis Steffen (23:08.718): I learned on my first raise—investors punched me on retention. We failed to fundraise and sold later after fixing churn to a buyer who valued the solution.

Jason Kirby (24:24.449): Your first raise attempt was $1.5M, but churn derailed it.

Travis Steffen (24:37.582): With UpShare, we got 250K installs in three months but lost most—automatic churn. Investors refused to round. We learned: bail water or plug leaks. So I researched and later built retention-focused ventures.

Jason Kirby (29:47.237): Tell us another churn-killer story.

Travis Steffen (30:46.154): GrowthTeam: an AI growth leader concept failed—90–120 day retention, niche needs too varied. We shut it; retention puzzles even veterans.

Jason Kirby (35:39.557): AI hype can’t replace human relationships in deals or retention. It's a great intern but not a CEO.

Travis Steffen (38:54.368): Growflow turnaround—licensed US cannabis compliance software grew from low to $10M in 3 years. We won through ‘most helpful company’ ethos: hiring former operators as support, mastering empathy and predictability.

Jason Kirby (43:40.933): That ethos led to a $70M exit. Amazing example of plugging churn leaks via service intensity.

Travis Steffen (48:36.52): Now Rivalto: done‑for‑you retention, 20% outcome-based commission on MRR saved, $1K free recoveries for listeners. We handle involuntary, voluntary churn, surveys, AI-driven insights, shared Slack channel. Proven across $8→$7K/mo subscriptions.

Jason Kirby (57:08.421): No upfront fees—performance-based. Founders must fix churn before M&A or fundraising.

Travis Steffen (58:16.005): Visit rivalto.com to schedule demo. Start in 15 minutes. Use code DEMYSTIFIED for $1K free recoveries. See proof at rivalto.com/proof.

Jason Kirby (59:08.941): Final advice: treat churn like a product—assign owners, KPIs, experiments. Ask why customers leave, preempt feelings, manage expectations honestly.

Travis Steffen (01:01:39.917): Yes—build retention habits: survey cancels, save them with incentives, improve product to avoid triggers. Honesty over hype retains customers.