Episode 837 | How Do You Learn Product? and Optimizing Your Trial Funnel (with Ruben Gamez) artwork

Episode 837 | How Do You Learn Product? and Optimizing Your Trial Funnel (with Ruben Gamez)

Startups For the Rest of Us

June 16, 2026

How does a founder actually learn the skill of product? In this episode, Rob Walling talks with Ruben Gamez of SignWell and Bidsketch to answer listener questions that turned into a much deeper conversation than expected.
Speakers: Rob Walling, Ruben Gamez, Ryan
**Rob Walling** (0:00)
Welcome back to another episode of Startups For the Rest of Us. I'm Rob Walling, and in this episode, I have fan favorite Ruben Gamez back on the show, and we answer some listener questions. And in this episode, I actually earmarked five questions that we were going to run through, and we only made it through two because we went so deep on these. First question was about optimizing a trial funnel, when to add friction, when that works, when it doesn't, because Ruben runs two different SaaS companies, Bidsketch and SignWell, and different levels of friction work differently for those two companies, so he has a lot to say on the topic. And then we dive into a question about the core four SaaS skills, Dev, Sales, Marketing, and Product, and someone asked me, how do you learn product? And so we spend, I don't even remember, 10-15 minutes talking through how we learned how to make product decisions. I think it turned out to be a great episode. Before we dive in, I want to let you know about the SaaS Institute Cancun Retreat we're having in early December. So it's going to be a two and a half day high-level knowledge sharing event exclusively for seven and eight-figure SaaS founders.
I know how hard it is for founders at your level, at seven and eight figures, to find a group that is at or ahead of them, and this event will be that. You're the average of the people you spend time with, and the SaaS Institute Cancun Retreat is going to be filled with ambitious people who are executing. It's a small group retreat focused on founders sharing real behind-the-scenes knowledge on what's working, building relationships, and taking a step away from the day-to-day to figure out the next big picture move. It's going to be at one of the top resorts in Cancun, close to the airport, December 5th through the 7th.
And as I mentioned, while this event will be focused on SaaS Institute founders, there is a chance we might open a limited number of tickets to other qualified 7-figure founders. You can email Tracy at tinyseed.com if you want to get on that wait list. It's going to be a great event. I'm really looking forward to it. And finally, if your company serves SaaS founders, we have a few sponsorship opportunities open right now, including this podcast at Microconf Iceland and in our Micro Newsletter. It's a great way to get your business in front of thousands of SaaS founders who are actively building and growing their companies. We're definitely selective about who we work with. We actually turn quite a few sponsors away because we want it to be a strong fit for our audience. And if you're interested, reach out to producer Ron, who's heading up all our partnerships, and that's sponsors at tinyseed.com. That's sponsors at tinyseed.com, and it'll go directly to producer Ron. And with that, let's dive into my conversation with Ruben.
Ruben Gamez back by Popular Demand. Thanks for coming on the show again, man.

**Ruben Gamez** (2:59)
Hey, thanks for the invite.

**Rob Walling** (3:01)
I always love recording with you. It's fun and informative. So we are gonna dive into some listener questions today.
The first question, I love it. I love it when people do this. So Ryan emails in and says specifically, I have a question for the next time you have Ruben on the show. And it's like, anyone, if you're listening to this, please do that for any, I know Derek Reimer is coming back, I can get Jordan Gall coming back, I can get Craig Hewitt, I can get Rupe, anybody who's been, you want a question for Laura Roeder, you want, like, name someone by name, and I will get them on. Like, it's a great excuse and a reminder. Because man, I think, you know, producer Ron told me, you haven't been on for, I think it's been a year, I think it was June of last year, and I was like, wait, that's, that can't be right. And then I looked and it's right. It just goes quick, right? So it's a good excuse to have you back on the show.

**Ruben Gamez** (3:49)
Cool.

**Rob Walling** (3:49)
And so Ryan wrote in, or actually he sent a voicemail and we're going to play that right now.

**Ryan** (4:00)
Hi, Rob. I was listening to the latest episode of the Offsite Podcast with Jordan Gala and Ruben Gamez.
And towards the end of the podcast, I'm talking about friction during the trial flow. Ruben mentioned that friction works pretty well for Bidsketch, his proposal software, but SignWell, his e-signature software needs to be frictionless. With my own project management SaaS, I have about a two-week trial, but users often need a lot more time than that. And I've thought about ways of trying to accommodate this, but maybe it is better for them to contact me than forget about a month-long trial or a premium product. It would be interesting to explore the idea of friction a bit further and even better if you could discuss with Ruben next time he's on the show. Thanks.

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