Bubba Page: [00:00] I felt that I was a failure personally because I had tied myself and my reputation to the business so that when the business didn’t work out, then I looked at me and said, “Well then, I’m—something’s wrong with me.”

Joe Grover: [00:13] Welcome to The Real F Word.

Joe Grover: [00:20] Welcome back to The Real F Word podcast. And I’m so excited to have Bubba Page here. Bubba is a great friend of mine. In fact, we were just talking: We couldn’t scroll back far enough; it was probably 2008. In fact, I knew Bubba before people called him Bubba. 

Bubba Page: [00:35] That’s true.

Joe Grover: [00:36] Right? He was still going by his given name and not Bubba. But Bubba is a successful entrepreneur but also has felt the sting of defeat, and we’re going to talk about that today.

[00:46] And the thing that’s interesting, Bubba, about this approach—and you know this well because I remember the two of us sitting down for lunch after I had failed in one of my startups in Colorado, and I shared a lot with you. I shared how painful it was. And I was really still trying to process all of that. And you had a different experience, but one where the company that you had invested in and had raised money for and had built the team and had some early traction didn’t really reach its potential and failed. And I remember us talking about talking about this. And specifically, I don’t know if you remember, we were going to start a club called the Fail Club. And in order to be a member of the Fail Club—

Bubba Page: [01:27] You have to have failed.

Joe Grover: [01:29] Yeah, like a million bucks or more. We said, “If you’ve raised and lost a million dollars or more, you can be a member of the club.”

Bubba Page: [01:35] Maybe that’s what needs to happen.

Joe Grover: [01:36] But if you’ve just had success—I know, right? So maybe we should launch the Fail Club alongside The Real F Word podcast. So welcome and thank you so much for being here. 

Bubba Page: [01:45] Hey, thanks for having me. There’s so much history. There’s a song by Ben Rector called “Old Friends.” Have you heard of this? It’s like one of my favorite songs. If you haven’t heard it, go listen to it. It’s amazing. You are one of those old friends.

Joe Grover: [01:58] I know, and that’s why one of my first calls was to Bubba. As we were thinking about this podcast and launching The Real F Word, I thought, “I want to have this conversation again with Bubba,” because I know that you’ll be unfiltered about the experience. And we certainly—you have a lot of success that validates your capabilities as an entrepreneur. But today, we don’t talk about any of that. We don’t talk about any of the success. We’re just going to talk about your experience building Outro. And I want you to just share that story. In fact, I remember we met in Boulder, Colorado, when I lived in Denver, when you were there at Techstars, and there’s probably a little bit of a precursor to that. So tell me the story of Outro. Why did you start it? How much money did you raise? What was the vision for the business?

Bubba Page: [02:44] All right, so let’s start at the beginning. So I was running a company called Launch Leads, so this gives you an idea. Started in 2009, an outsourced B2B appointment-setting company. You would call them today SDRs or BDRs. That’s what the terminology is today. Service-based company, bootstrapped. Cash-flowing business. Service business.

[03:13] I had read the book by Clayton Christensen, The Innovator’s Dilemma, and I thought to myself, “Okay, possibly, this business won’t exist in the future, and so what is the next version of what I’m doing, and how can I be the one to build that?” was the first idea. But I put that on the shelf. I just put it on the shelf. I remember reading in magazines and thinking, “Oh my gosh. Look at all these venture-backed startups.” They’re getting huge multiples at the time, and I’m doing a service-based company, and I’m starting to realize that my multiple on EBITDA to exit was quite low. Maybe it was 1–3x EBITDA, or 3–5x if you’re really, really cranking. And some of these tech companies were getting 10+x multiples. And I thought, “Oh my gosh, I got to get into tech. This is where I got to go.” So with the idea of morphing this business into something that could continue for a long time and the desire of “I want to learn venture capital, I want to understand that world, and I would love to have the multiples of a software company,” that’s where the idea came.

[04:24] I didn’t do anything about it, though, until I went to a Google Startup Weekend, and this Google Startup Weekend essentially was a competition where you had, I don’t know, 100+ people there. You spent Friday, Saturday, that’s it: just Friday and Saturday working on a business. Everybody could pitch a business, and it was 60 seconds to pitch. And I came there. I was asked to be there as a mentor, so I went there to mentor other entrepreneurs. And then when they said anybody can pitch the idea, I was like, “Well, I mean, I got an idea. Maybe I’ll pitch.” 

[04:58] So I ended up pitching this concept. At the time, it was called QuotaDeck. I didn’t have a name for it at the time, but we just came up with QuotaDeck because we were going to help people fulfill their quotas. And the idea behind it at the time was this 1099 sales rep that could rep multiple technology companies at once who were targeting the same demographic. So if you were targeting CMOs, you might have five to 10 companies that you could sell to that same CMO, because a lot of it is based on the relationship and the hardest part is getting in the door, setting an appointment, getting the decision maker. Anyway, probably too much info on the actual product. 

[05:41] We ended up winning. So we won that competition, and they went to the national. So that was like Utah startup weekend. And then we got invited to pitch at the national competition. Didn’t win the national competition, but ended up applying to Techstars. I would call it the number two accelerator in the country. Y Combinator is what most people know about. And so in 2014, I got invited to come to the Boulder headquarters of Techstars. I was one of the earliest Utah companies to ever be accepted into Techstars. I tried Y Combinator and didn’t make it—got through the interviews. 

[06:21] But this idea behind starting the software company became really, really exciting. And the more I talked about it to people, the more excited people would get. And it was like it was on fire. It was downhill. It was easy. The ball had so much momentum—the stone, whatever you want to call it. And things just came. I mean, I only had a couple meetings with investors. First check came, and I’m like, “Oh my gosh! Is this what raising venture capital is like?”

Joe Grover: [06:53] Too easy.

Bubba Page: [06:53] It’s not. I just got really lucky. But I think one of the reasons I was able to raise capital so easily was that I had almost a decade of industry experience. And specifically, I had clients that were the VC’s portfolio companies. So they had already known my name, they had seen me around, they had heard of what I’ve done in that similar industry, and so when I came to them with this tech idea, they were like, “Hey, this is a repeat founder. He knows the industry, he knows what’s coming, he’s done it before, and he’s got a profitable business already. Let’s give him a shot.” 

Joe Grover: [07:30] “What could go wrong?”

Bubba Page: [07:31] “And he’s accepted into this prestigious Techstars.”

Joe Grover: [07:34] “Yeah, what could go wrong?”

Bubba Page: [07:35] “And what could go wrong?” So they wrote the first check. Peterson Ventures, Kickstart Seed Fund, Techstars came in, and then a small group out of Arizona called Tallwave Capital. And then shout out to my two angel investors, which I love to this day: Brent Thompson and Joe Atkin. 

Joe Grover: [07:52] Both great entrepreneurs.

Bubba Page: [07:53] Just unbelievable entrepreneurs. And they saw vision. They believed in me, and I was delighted to have them be a part of the ride. Went through Techstars. I ended up recruiting a CTO (fractional CTO at the time), and then a designer, because I didn’t know how to build a tech product. So I had a CTO and a designer—so I had the back and front end—and then I was a business guy. And I ended up getting another person to come on board who helped us from a marketing and salesy type position. Anyway, three to four months in, that’s when we got to see each other. The Techstars experience was unreal. I learned so much: the network, the connections. If you could ever go through an accelerator, I think it’s hugely valuable. We ended up raising more capital through that process because it was first started at 400, and we ended up with 1.25 was our total raise. So not a ton, but for a first time fundraiser, that was pretty cool.

Joe Grover: [09:06] Yeah, that was your seed round. That’s the money you need to build a product to validate in the market, do a little bit of sales and marketing.

Bubba Page: [09:13] So we end up going to market and starting to get on clients. And the idea—so, it morphed, like most startups do. We pivoted from this 1099 salesperson idea to becoming more of a referral automation platform for our sales referrals and hiring referrals. And as we built out the technology, we would have our networks—I would upload my LinkedIn network into the system. It would—the algorithm, the AI, back in the day—

Joe Grover: [09:41] I remember doing this. 

Bubba Page: [09:42] Oh, yeah, because it was easy back in the day. You could download your LinkedIn contacts, easily upload the entire CSV, have all of the data, and then our algorithms would categorize who is everybody and how they’re connected so that when, let’s say, Joe, you came to me and said, “I wanted to talk to,” you wanted to talk to more CEOs. Well, in my network, I had a hundred CEOs. It would prompt me within the platform to say, “Hey, Bubba, you could introduce Joe to a hundred people. Which ones do you feel comfortable introducing to Joe?” And then I would just select, “Well, out of those hundred, I probably would feel comfortable with these 10 or 15.” And then it would automatically create this double opt-in intro. That’s what we called it. So, you had opted in, I had opted in, and then I was asking this person if they would be interested in an introduction.

[10:31] Long story short, we started getting checks from clients. So we had real revenue coming in. I think at one point we had 250 grand in revenue, which was this super positive, “We’re doing this.” 

Joe Grover: [10:46] A great signal. People are paying for your product. 

Bubba Page: [10:49] People are paying for the product. They want the product. We’ve built the product. The introductions are working, meaning the algorithms—the AI back in the day, before AI was a thing—was working. It was finding the right people, we were getting/making connections happen. But we couldn’t make enough connections happen. So the companies had prepaid, essentially, for credit on the system.

Joe Grover: [11:12] Oh, interesting. 

Bubba Page: [11:13] So the Domos of the world or a Pluralsight or these tech companies, they wanted these sales introductions. So they’d be like, “Yeah, here’s 20 grand. Go give me as many of these referrals as you can.” And as they would get the referrals, it would deduct out of their thing. Well, we started making introductions, but nowhere near as fast as we needed. So we really worked hard on the UI and the UX, like, “What’s wrong? Is it the product that’s wrong? What’s the psychology behind people making introductions?” And it was this deep, interesting dive. I read this book called Predictably Irrational, which I’d highly recommend for any technical cofounders. It is really fascinating that human beings are essentially predictably irrational. And it walks through a million scenarios of scientific evidence, and it helps you to build a better product. I remember listening to so many books on UI/UX, because for some reason we just could not—people were—

Joe Grover: [12:16] They weren’t making the referrals. 

Bubba Page: [12:17] They weren’t making enough. We had a baseline. 

Joe Grover: [12:21] So they have this credit—20,000 bucks—and you’re just chipping away and you couldn’t fulfill.

Bubba Page: [12:28] So that was the first problem.

Joe Grover: [12:30] So tell me about that moment where you’re like, “Uh-oh, I have a problem.” What was the signal that you were seeing?

Bubba Page: [12:35] It was like, “Oh, it just must be a UI/UX issue. So, team, let’s go. Let’s change it up. Let’s make it better. Let’s make it this.” Oh yeah, of course, you problem-solve. That’s what you do as an entrepreneur, right? So it was never like, “We’re screwed.” It was like, “Oh, let’s just fix it. Change this. Let’s change that. Let’s test this. AB that.” And we just could not get the volume of introductions to be happening fast enough at that level. And I think the concept of people uploading their contacts—we had ended up having two to three million contacts uploaded in the system. So that wasn’t even the problem. It was people actually following through and just clicking a box saying, “Yes, I am happy to introduce these people.” It was—

Joe Grover: [13:15] You were facilitating the entire introduction. They just had to opt in.

Bubba Page: [13:19] That’s all they had to do is just check the box. I agree.

Joe Grover: [13:21] You were drafting the email or the LinkedIn intro and a whole bit. 

Bubba Page: [13:26] And we thought that maybe there was something off with their incentive, like, “What is their incentive to make an introduction?” And at first, it was like, “Well, it’s good will. You’re making introductions to them because your people will make introductions for you.” And they’re like, “Well, do we need to add cash and a cash incentive?” And I’m like, “Well, there’s pros and cons of cash incentives. Because then there’s this money exchange, and does that change the vibe?” So we just kept testing, testing, testing, testing, testing to try and get this to work.

[13:51] And then, I think we weren’t the only companies trying to leverage LinkedIn’s API and our contacts, and they shut all of their API down. Now they couldn’t shut it down so that you could never get your contacts, but they made it a miserable experience. Today, if you download your LinkedIn contacts—for example, I have 23,000 followers on LinkedIn. If I downloaded—I did. I downloaded my contacts. I got 500 emails. That’s it from 23,000. So they are not willing to share everybody’s—and people have the right to not opt in to share with their contacts. Back in the day, you had everything.

[14:31] So two things: They first shut off the API, which was essentially how we got all of our data was through LinkedIn. So one error for sure was that we relied on this singular platform to be our data source. So when that happened, we’re like, “Okay, well, let’s jump to Google Contacts.” And so we were trying to figure out how to do Google Contacts. But Google Contacts were like your grandma and your aunt and uncle And it wasn’t the business people that we needed, nor did it have the form-filled pieces in it.

Joe Grover: [15:06] So how far into the business are you at this point? 

Bubba Page: [15:08] So we are in— 

Joe Grover: [15:10] A year or two?

Bubba Page: [15:10] We are in a year and a half by this point, because we had this traction. 

Joe Grover: [15:15] Early traction. 

Bubba Page: [15:17] Yeah, we got early traction, which gave us this almost a false positive. And so this false positive, we’re telling everybody, “We’re making it happen. Look, we got revenue, we’re making intros, it’s happening.” And then it was about a year and a half-ish that LinkedIn shut everybody off.

Joe Grover: [15:32] But even before LinkedIn shut it down—

Bubba Page: [15:34] There were still signals. 

Joe Grover: [15:35] There wasn’t enough velocity in the introductions to sustain business.

Bubba Page: [15:39] Yeah, so that velocity, but I never saw that as the issue. I really never did because I just thought that could be solvable. 

Joe Grover: [15:45] Ux issue. 

Bubba Page: [15:45] Yeah. Do we need an app? Is it an app issue? Do we need push notifications? Because back in the day, it was just a laptop/desktop functionality. So that wasn’t even what we thought was a problem. And so, as we continued to test and test and test, and then I ended up recruiting, let’s say a year into it, my cofounder, Dave Oldham (loved working with him; it was just so much fun), and then brought on Zach Barney on the sales side and some other amazing people. 

Joe Grover: [16:18] How big was the team at its height?

Bubba Page: [16:20] Oh, geez. I mean, we only had six, I think, at our height. 

Joe Grover: [16:22] Still small. 

Bubba Page: [16:23] But we were hiring, because we had this false positive: We had revenue!

Joe Grover: [16:27] Were you guys paying yourself from the money you raised? 

Bubba Page: [16:29] We had paid ourselves. Yeah, we had paid ourselves a very small percentage of what would normally be a salary. But then the second we—let’s see here: We were probably a year and a half into it is when we stopped paying—Dave and I stopped taking a paycheck. And we made that choice to keep the payroll going.

Joe Grover: [16:49] How much cash did you have in the bank at this point? 

Bubba Page: [16:51] Probably at that point, maybe only 250 grand or something like that.

Joe Grover: [16:55] So your cash balance is dwindling.

Bubba Page: [16:58] We were extremely cash efficient, so that could last us almost a year. 

Joe Grover: [17:03] You weren’t burning a lot of cash.

Bubba Page: [17:04] No, we were not burning it. I mean, we worked out of my basement office. It was literally they’d come to my house, walk into the basement, and we were working out of a room. And nobody was getting paid a ton. But we were generous with equity and things like that.

Joe Grover: [17:24] And just let’s talk about equity. So when you went out and raised money from these great investors, who we both respect, what was the vision that you painted for them? What did you think the financial outcome could be if you guys continue to execute over five or six or seven years? 

Bubba Page: [17:38] I mean, with the original concept, without even that false positive of revenue. They told me, they were like, “Bubba, this is a binary outcome. You will be the biggest thing out there, competing with LinkedIn potentially, or you’ll be nothing.” And I was like, “Okay.” 

Joe Grover: [17:56] Those are tough words now, right? 

Bubba Page: [17:58] It was give it a shot. You have to compete with a multibillion dollar company like LinkedIn. And I never thought that we would necessarily compete. I thought we would partner. I thought we’d get acquired by. I thought that’s maybe the direction we were going to go. But it was a binary. 

Joe Grover: [18:12] It was a billion dollars or bust, right? That was what everyone thought. That’s what you thought. You thought, “Listen, if this goes well, this is my last thing, right? And I’ll retire and climb Mount Everest. But if it doesn’t work out, it was going to be a bust.” So you had your eyes wide open going into it. 

Bubba Page: [18:29] Oh, for sure 

Joe Grover: [18:30] This was a little bit of a swing-for-the-fences-type opportunity.

Bubba Page: [18:33] A hundred percent. And I was okay with that because I had built this steady cash-flow business, profitable business, services business that was great, and it was steadily growing, Inc. 5,000 three years in a row. I had hired a CEO to run it day to day, and he was doing a great job. I had given him equity and salary.

Joe Grover: [18:50] I think you offered the CEO gig to me once. 

Bubba Page: [18:52] I did.

Joe Grover: [18:53] Remember that?

Bubba Page: [18:53] Oh yeah. 

Joe Grover: [18:54] Remember when we had that conversation?

Bubba Page: [18:55] I wanted you to do it. 

Joe Grover: [18:55] I probably should have. 

Bubba Page: [18:56] I don’t know. Who knows. Everything happened for a reason, but yeah it was an interesting vibe, because I think I’m a glass-half-full-type of a person. Always have been. So, as we would come into problems, I would just sit down and “How do you fix it? How do you solve it?” That’s just what you do. And that’s how I always approach everything. And then I believe, as a sales-oriented entrepreneur, sales and revenue solve most problems. 

Joe Grover: [19:25] Sure.

Bubba Page: [19:26] It was/is my belief—it still is my belief—that most problems, though not all problems. And so I just thought, “Well, let’s just sell to get ahead of it.” So I brought in more salespeople and we sell. 

Joe Grover: [19:38] Brute force. Just sell more clients.

Bubba Page: [19:42] But the reality is that was the easy part, and we didn’t know that. So we were getting these, because they all wanted what we had. What we were promising they wanted. They wanted more sales leads. They wanted more hiring referrals. 

Joe Grover: [19:54] You had identified a pain. You had identified a clear need. 

Bubba Page: [19:57] We had nailed the pain for sure, 

Joe Grover: [19:59] The message market fit was spot on, and that’s evidenced by the frictionless sales process. But the delivery, you couldn’t deliver on the brand promise. Is that— 

Bubba Page: [20:10] Totally.

Joe Grover: [20:11] That’s what happened.

Bubba Page: [20:11] And now that I can look back—so, we ended up shutting it down at about two and a half years into it. 

Joe Grover: [20:16] Okay, so you’re two and a half years in. Let’s—

Bubba Page: [20:18] So yeah, so we had to let people go at year two. 

Joe Grover: [20:20] Okay, tell me about that. 

Bubba Page: [20:22] Oh, so painful. Don’t get me wrong: I’ve hired and fired 200 plus people in my career. I had laid people off. It was years earlier. In our previous business, I had six of our biggest clients all quit at the same time, and so we had to lay people off. But for whatever reason, this one, it stung so deep. Family, right? This was a very small group. These are people that I respected, that I loved. We saw the vision together, and we were seeing the success happen together. And so when it stopped, we were all just bewildered. Why? Why is this not working? How come we can’t change the UI/UX well enough to get people to do it? So I think all of us were in this, pondering about why. Why? How did this not work? I remember we’d go to our investors, and I tried to keep our investors up to speed the whole time, like, “Hey, look, we’re struggling. We found this, this is great, but this isn’t working. Hey, we did this. It’s awesome. This thing isn’t still working here. We got revenue, but we’re struck.” And then LinkedIn, oh my gosh. 

[21:32] And then when we came to them, and we had probably six months of runway left—six months of runway with no team, just to keep operations going and keep the site up, and no salaries or anything like that—we went to the investors, like, “Look, we have these five tests that we could do, and if we do these five tests, there’s a chance that we could hit it, and it could succeed. But I can’t—” And I was honest. I said, “Look, but I can’t promise.” 

Joe Grover: [22:02] So you had five bets. 

Bubba Page: [22:04] Five bets. But if we had these five bets, then we would need a little bit extra runway. 

Joe Grover: [22:09] How much more capital? 

Bubba Page: [22:10] Like another 250 grand. And be like, “Okay, if we had these five bets, I think we could do it, and I think there’s a chance we can hit it. But I won’t and I can’t guarantee that. I’m going to be honest with you. I just don’t know.” And they looked at me in the eye and they were like, “Look, Bubba, we love you, we think this idea is great, but I don’t think it’s the right time to put more capital into it.” And I remember the dagger that just felt in my soul. 

Joe Grover: [22:38] Because you knew that was it when they said— 

Bubba Page: [22:40] Yeah, when they were like— 

Joe Grover: [22:40] “We’re done.” 

Bubba Page: [22:41] “We’re not going to put more cap.” Yeah and I knew that the signal behind my investors, who had invested in us the whole way, if I were to go try to raise additional capital outside, with them saying, “No,” very, very, very small chances. So they essentially said, “Look, try and find a soft landing.” And I was like, “Well, I’ve never done that before. But I’m a sales—”

Joe Grover: [23:04] Is there such a thing? 

Bubba Page: [23:05] Yeah, “I’m a sales-oriented entrepreneur. Let me see if I can do this.” So I essentially spent the next six months solely trying to generate a buyer for the assets, for the connections, for the user base, whatever. And I found that it is a lot harder to sell a business than to be acquired. Those two are very different things. 

Joe Grover: [23:32] For sure.

Bubba Page: [23:33] When you have people approaching you to get acquired versus you pitching your business, it is very—I won’t say that it’s not impossible, but I failed. I failed at getting that done. And I worked.

Joe Grover: [23:46] How many conversations did you have with potential buyers? 

Bubba Page: [23:47] Oh, I probably still have, well, maybe not on the spreadsheet, but at least 150 people.

Joe Grover: [23:55] Anyone that could benefit from the product or the traction or the technology. You were just trying. 

Bubba Page: [24:02] I’d even talk to small PE firms about, “Could you wrap this in or roll this in? 

Joe Grover: [24:06] “Roll it up.” And did anyone get serious in the acquisition?

Bubba Page: [24:02] Yeah, yeah. So we had a funnel and went through the funnel and landed with seven truly interested buyers. And I thought, “Hey, this is seven. We could do a little bidding. Maybe we can actually get something real out of this.” And essentially, in the end, all of them were like, “Nah, we’re gonna pass. Sorry, we’re gonna pass.” 

Joe Grover: [24:27] When you were down to the last one, because I’ve been in this situation where my only reasonably positive outcome would be to sell the asset or sell the business, and I remember the moment that the last potential acquirer came and said, “Hey—” in fact, this other business, it was the LA Times— 

Bubba Page: [24:47] Oh my gosh.

Joe Grover: [24:48] —who had their own set of issues, and they were just like, “Hey, we looked at it.” And I knew the moment they said no, it was like the domino. And then everything that happened after was super painful. What was that moment? Do you remember the last potential acquirer? When they told you, “Hey, we’re not going to do it”?

Bubba Page: [25:06] I don’t remember the name of them, but I do remember getting off the phone and looking at Dave, who—he and I have now been working for a long time without any pay and with the hope and dream of making this work. And I do believe there was quite a few months where I even told Dave, “Look, you don’t need to work. Go find your next thing. I’ll just try and sell it.” But I remember calling him up and just saying, “Look, dude, I don’t think this is going to happen. I just don’t think there’s anyone out there.” And LinkedIn was still closed down. So, we didn’t necessarily have a solution for some of the problems that we had faced already. 

[25:47] But I personally went into what I think was my first level of depression and anxiety was in that moment of my life where I felt like—and this is a big caveat I want people to hear—I felt that I was a failure personally because I had tied myself and my reputation to the business so that when the business didn’t work out, then I looked at me and said, “Well then, I’m—something’s wrong with me.”

[26:17] And it was incredible because some of these investors—I didn’t recognize it at the time, but they would set me down and be like, “Look, Bubba, we know it’s not your fault. You worked incredibly hard. You kept us up to date on everything. And if you were to start a new company, we’d back you again.”

[26:39] And I remember when I heard that, it didn’t fully penetrate because I was so down on myself. But now that I look in the past, I can see that that was like this glowing light that, although it didn’t penetrate at the time, it grew over time, and it helped me to rebuild some of that confidence. But it took years to rebuild confidence, which is embarrassing, to say the least. But I remember the depths of depression was probably a six-month timeframe where I just wasn’t myself. It was hard on my marriage. It was hard on my outside relationships. My career basically stopped. And I ended up becoming a prepper. And I started prepping. And I had this religious awakening, and I started exercising more.

[27:34] I started putting in some good priorities into my life that I can now look back and say that I’m grateful for. But I was in the depths of hell, for sure, in that context. I’ve since been through harder things, but that was extremely difficult at the time. And the worst was my friends—the angel investors—to have to go to them and say, “I don’t have your money, and I literally cannot return you any capital.” Because we tried for so long thinking there was hope to sell, hope to sell, hope to sell.

Joe Grover: [28:12] Yeah, “You trusted me.” I had that experience, right?

Bubba Page: [28:15] Oh yeah.

Joe Grover: [28:16] And it is incredibly painful to be able to just acknowledge I did everything I could, but there’s not going to be a dime back from that money that you invested and there’s really nothing. Sometimes you feel like there’s nothing to show for it.

Bubba Page: [28:31] Oh yeah, 

Joe Grover: [28:32] And you’re just like— 

Bubba Page: [28:33] “I worked my tail off for almost three years, and I’ve got nothing to show for it.” 

Joe Grover: [28:35] “How am I going to pay back my family for all the time and sacrifice? How am I going to pay back my investors who trusted me?” Right? And you’re a steward of this capital. And then, when it doesn’t work out, it does feel personal. 

Joe Grover: [28:48] What’s up, fail fans? You know, as we’ve listened to so many guests on this podcast, that the road to success is often paved with failure, with a lot of challenges, and even full-on face-plants. But there’s a thing that you could do to help skip some of those bumps and bruises, and that’s really where the consultants at Amplēo come in. See, Amplēo offers fractional executives in finance, marketing, and HR. And these are people who’ve experienced a lot. They’ve been in the trenches. They’ve built businesses. They’ve failed. But here’s the kicker: They’ve learned from those failures, and now they’re applying all that wisdom to your business to support you so you don’t have to learn the hard way. I mean, think about it: Instead of stumbling around in the dark and hoping you don’t hit the wall, you could bring someone in who’s already mapped out that room, right? Amplēo consultants and experts have worked with and for numerous companies of all sizes, and they’ve gathered insights on what works and where to focus and how to actually grow your business efficiently.

[29:48] So while we embrace failure on this podcast, there is no rule that says you have to fail at everything yourself. So check out Amplēo and see how their fractional executives can help your business move forward and avoid those painful learning curves. Sometimes the smartest move is learning from someone else’s failure. Visit Amplēo.com to learn more. 

Joe Grover: [30:10] Tell me: You used the word depression, and I just want to talk about that for a minute. You are a really optimistic person. You’re a—you said it earlier—you’re a glass-half-full person, and I know this about you, Bubba. Why do you think a failed startup, which is such a common outcome, had that type of emotional impact for you?

Bubba Page: [30:31] Well, I think there was probably some insecurities that I had not addressed from even my childhood. And I know this goes way back, but we all have insecurities. I’ve been learning a lot about them in the recent year. And I think our childhood wounds—and I’m not talking about big T trauma, but little T trauma. My parents were amazing. They were phenomenal. I had great siblings. What a wonderful upbringing I had. But we all have our issues of our upbringing. And I think I was a black sheep of the family. I have doctors, dentists, lawyers. I’m the only entrepreneur. I remember in college getting involved in my first startup, borrowing five grand from my parents to invest in my startup to earn equity. And I knew that they didn’t believe in it. They were just donating that money knowing that it would never come back. And when I did pay them back plus interest, because I was able to sell my ownership, I had this pride of “See? I’m going to show you that I can do this.” 

[31:38] Well, why did I have a chip on my shoulder? I’m the youngest child. I was always the baby, and I was this black sheep. I never got the scholarships like my siblings did. I didn’t get the straight A’s like my siblings did. I did well in sports, so that was where I found myself was like a sports person. But if you think deeply enough about us as adults, a lot of who we are and what we’ve become is because of our childhood upbringing. All of it. And this chip on my shoulder is what got me to start my next business. 

[32:15] So from that little college business to then doing the one after Junto Partners, which you and I did together in 2008, and in 2009, when I started, I was like, “No, I’m going to go do this.” I was oblivious and naive to what the outcome could be. But it worked. And it took me a few years to get it stable, but then it really grew. And earning a half a million dollars a year as a salary is not bad for a 20-something-year-old. And so I look back at running this venture-backed startup, the opportunity costs of losing that type of salary for two and a half years. That adds up. And so that’s me investing into that other startup. 

[32:59] Anyway, the thing that I want people to realize is that if your business fails and you’ve tried everything that you can in your power to do and work as hard as you possibly can, know that you personally are not a failure, that it was the business that failed. And if you can understand that it was the business that failed, and the faster you can get back up and keep going and start something else, even if that start something else means you go get a job, there’s nothing wrong with that. But the sooner you get back on your feet, dust yourself off, and get back in, the better you’ll be off, I think.

[33:39] I was in a position where I didn’t have to go back to work right away, and so I took this time, and it was healing for me, and I feel like there was—exercise and health was a really important part. God was a huge element for it. I have always been a God-fearing person, a faith-based person, but I hadn’t been reborn yet. I hadn’t had an awakening yet. And now I look back and I say I can see that God used this experience for me to wake me up to the reality of my circumstances and for me to recognize that life wasn’t just about being on cover of magazines, thousands of employees, and hundreds of millions of dollars. That’s what He needed me to learn.

[34:34] And even though I felt inspired to begin the business in the first place, I felt like God told me to start the business. And it didn’t work. You’d think, “Well, why God? You told me to do it, but it didn’t work. What the heck?” And I think the way I look at it now is I see the lessons I needed to learn personally, and He used this experience to humble me, to bring me to trust in Him more and to dedicate more of my life to Him. And so that year, 2016–17, was a year that I turned my own personal self around, really rededicated myself to God and church and scripture study and trying to cleanse myself and become a better person.

[35:30] I don’t think I would have gotten to that point without this level of failure. And there’s opposition in all things, we’re taught. So I had this horrific experience and then I was brought into this light. And I just see God using these experiences to teach me what I was supposed to learn. And since then, it’s been almost close to, what is it? Seven years? Eight years? I can see that pattern that I’ve still failed on other things in life and in work, whatever it is, and He’s leveraging these experiences to teach me what I need to learn.

[36:09] And I just think there’s a lot—going back to our childhood thing, sorry, I got off tangent. I think if we can start to recognize our relationships with our mother and our father and how—there’s a book called Attached. I would highly recommend it. It talks about attachment styles and theory around attachment, being anxious or avoidant and wanting to be secure. There’s so much healing that can be had for all adults if we understood why we are and why we act the way we do. Anyway, there’s a whole other tangent there.

Joe Grover: [36:44] So how long did it take you? I love that you’ve shared some of the coping mechanisms, what you had to rely on as you were going through this really dark period of your life, and I love that physical fitness and faith. I think you talked about becoming a prepper. That’s an interesting twist. I remember coming over to your place and you’re like, “Check this out!” and there’s a big room filled with food and supplies. But how long did it really take you to build your confidence and get ready for the next venture, the next big project? 

Bubba Page: [37:19] I hate to admit this, but, so, 2017, we’re in 2024. Seven years later, I’m still working on it. There’s elements of my confidence that have been shattered, and I ended up going from that business that didn’t work out and taking some time off prepping. And then I joined the mom of my kids with her business and started building that. And it was a soft landing for me. It was working. We were growing. I felt like I was utilizing my skills properly and building a team and systems and processes. But I essentially decided to put my career on hold because I had a spouse that wanted to grow—

Joe Grover: [38:14] Had a thriving business.

Bubba Page: [38:16] Yeah, wanted to grow and do her goals and passions. Well, she had supported me for 10 years, so of course I would support. Why not? But what I didn’t recognize is that when I did that, I didn’t fully overcome my fears. 

Joe Grover: [38:32] Right.

Bubba Page: [38:34] And although we grew and were very profitable and had plenty of success in those entities, I think, personally, I limited myself.

Joe Grover: [38:46] Never restored your confidence. 

Bubba Page: [38:48] Uh-huh. And it was about a year and a half ago, two years ago, that it was time to not do that business together anymore. And that’s when I was like, “Okay, what am I going to do? What am I going to do? I need to rebuild myself.” And you and I talked early on about it. And it took me way longer than it should have to figure out what I was going to do. I just wanted to be so calculated. 

Joe Grover: [39:16] Because of the fear of failure.

Bubba Page: [39:18] Because of the fear of failure.

Joe Grover: [39:20] I feel the same way. You just want to make sure that you don’t get yourself into that spot again because of the cost, the emotional and mental health tax that comes with entrepreneurship generally, and especially when it doesn’t go like you had planned. 

Bubba Page: [39:34] I think the younger you are—I highly recommend starting businesses the younger you are. I know you’re going to think, “Well, I don’t have any experience. I’m not an expert in something. I’m naive.” And you know what? Those are all awesome characteristics because the more you’ve been around the block, the more you know it will most likely fail, because they usually do. Businesses—what is the, I don’t even know what the percentage is anymore, but a lot—

Joe Grover: [40:02] It’s the most probable outcome of every startup. But we never have this conversation the way we’re having it today. And I appreciate your openness and vulnerability. I just want, what’s the—when you think back to Outro, what would you do different? Because it’s easy to ascribe a failure to something outside of our control. 

Bubba Page: [40:23] Yeah. 

Joe Grover: [40:23] We talk a lot about this: It’s the market. It’s capital. It’s competition. It’s LinkedIn, the LinkedIn API. There’s no way I could rebound after that. But what did you do wrong? When you’ve reflected on that, what are the two or three lessons that you want to ensure that you never make those decisions or those mistakes again?

Bubba Page: [40:43] Let’s see. I think one of them is I probably hired too soon. I think the false positives gave me this hope, and being a sales-driven entrepreneur, where that is part of my expertise, that is something I knew how to do. 

Joe Grover: [40:58] Hire sales people.

Bubba Page: [41:00] Build a team, hire sales, go, go go. I think we did that way too soon, now that I look at it, because that could have extended runway. There were probably three hires that we shouldn’t have had, 

Joe Grover: [41:12] So you would have just continued founder-led sales for a longer period of time before you brought in more sales people. 

Bubba Page: [41:20] Yeah, but what was so interesting is that I did that in part because I needed to go raise additional capital. 

Joe Grover: [41:24] Yeah, of course. 

Bubba Page: [41:25] And when you’re raising capital, that’s at least a half-time job. 

Joe Grover: [41:29] Yeah, it’s a full-time sales job is what it is. 

Bubba Page: [41:31] And so my ability to close more sales was limited because I was raising capital, so I brought in sales people to continue that.

Joe Grover: [41:39] But if you would have spent the same amount of time selling the product to customers, you might have been able to solve some of your problem with revenue versus with outside capital. 

Bubba Page: [41:48] Yeah, so I’d say that was a mistake for sure. Being reliant on a single entity like LinkedIn, that was a problem. That was a mistake. We just never thought ever that they would ever shut down our API. Why? It’s our personal—so, building? A lot of people build an Instagram thing. It’s like, “Okay. Be aware they may just shut you off one day.”

Joe Grover: [42:14] They’ll do whatever they want, whenever they want, with complete disregard for your startup.

Bubba Page: [42:18] Yeah, totally. And there’s many, many stories like that. So be aware If you’re building something that is attached— 

Joe Grover: [42:26] Dependent on—

Bubba Page: [42:27] Dependent is the right word. That’s not the right business model. Diversify at least outside of just one. Another mistake: I should have stayed healthier throughout the process—physically healthier and probably mentally healthier. I think I was so worried and so nervous and anxious about the business succeeding that I put exercise and eating right and sleeping right on the back burner. And that was probably my worst physical fitness state of my life.

Joe Grover: [43:10] Do you think that impacted your performance? 

Bubba Page: [42:13] Oh, for sure.

Joe Grover: [43:14] As a leader? As a founder? 

Bubba Page: [42:15] I think so. Even purely confidence. If you don’t—I love CrossFit. It’s been a really good thing for me.

Joe Grover: [43:21] You look great now. 

Bubba Page: [43:22] Thank you. I appreciate it. But I went working really hard. And I think that dedication—I think you have a clearer mind. You have the right chemicals going through your body. If you’re eating healthier foods, you’re going to be—I think your brain is stronger. Your body’s stronger. Your emotional well-being is stronger. I do agree that I wasn’t close enough. I should have been closer to God through the process as well. So, if we’re—the buck stops with me. I was a founder CEO. The business failed because of me and my choices and decisions. Sure, they’re extenuating circumstances, but I accept that as a CEO founder, I am the last straw. And so these are things that I bring up because my relationship with God, although I was still going to church, I had not dedicated myself to Him like I believe I should be. And the health side and family, I lived away from my family for three and a half months, and I’d come and see them every couple of weeks or two, three weeks or something— 

Joe Grover: [44:28] You were in Boulder, and they lived here in Salt Lake, 

Bubba Page: [44:30] My wife, we had three kids. Fourth was on the way. That was an incredibly difficult time, a very difficult time. She was supportive for me to go, but through the process, it was incredibly difficult. Now people have to go in the military. People have to go on job sites. People have to do things like this. So it’s not that you can’t succeed in doing it. For us it was a huge blow. And so I don’t believe that was best.

Joe Grover: [45:03] Some of those relationships were weakened through that entrepreneurial journey with Outro. What would you have done different?

Bubba Page: [45:10] So, as a young entrepreneur, I had a goals list. Very temporally driven: millions of dollars, hundreds of employees, covers of magazines, awards. That’s what I desired. 

Joe Grover: [45:26] That’s how you were measuring your success.

Bubba Page: [45:28] I was measuring my success on that. And I look at that now in the past and I say, “Because of my upbringing, I felt like that was the only way I could prove my worth in the world was if I accomplished these things and I became a multimillionaire and won all the awards. Then finally, they would respect me, and I wouldn’t be the black sheep anymore.” I didn’t think that along the way. That wasn’t a conscious thought. I can now look backward and say, “Ah, I think those are some of my little tweaks that I was doing.” So changing your desire. There’s nothing wrong with wanting to have financial freedom. I don’t think there’s anything wrong with that. But I think if you put that over the most important things in your life, it may cause problems. And so I knew that going away from the family was a temporary time and I’d be back. So for that temporary time, I thought it’d be okay to sacrifice from a family perspective. I look now and I say, “Maybe that wasn’t the best.”

Joe Grover: [46:35] I feel the same way. You and I talked about this. I spent five years working for a company in Colorado, and three of those years I lived here in Salt Lake in a condo, downtown Denver. And I spent far too many nights in my condo in Denver versus in my bed with my family and at home with my family. I think back and I’ve had that same learning that the price was not worth the benefit or the reward. Period. Even if it would have been a massive financial outcome. Those are nights that I can never get back. And it doesn’t mean we don’t have to travel sometimes.

Bubba Page: [47:13] Of course.

Joe Grover: [47:14] But if I had a do-over, that’s one of the things that I would— 

Bubba Page: [47:17] I mean, six kids right here, eight kids right here— 

Joe Grover: [47:19] We could—we’ve done our part. 

Bubba Page: [47:21] I think it’s important to remember. I mean, young entrepreneurs, you’re just grinding. You’re just doing— 

Joe Grover: [47:26] Whatever it takes, right? Whatever it takes.

Bubba Page: [47:29] And there is an element of that, and I know are VCs who will say, “I will only fund people who will do whatever it takes.” I’m not that guy. So when I’m writing checks now as Influence.vc, I want to see some more balance. And I may miss out on some incredible business opportunities. But if I can tell that this person loves his Lambo more than he loves his family, that’s probably not the right guy for me.

Joe Grover: [47:54] Yeah, I don’t invest in anyone with Lambos. That’s part of my investment criteria. If you have a Lambo and you’re funding your own business—

Bubba Page: [48:03] That’s right, sell your car.

Joe Grover: [48:04] You’re not using my money. 

Bubba Page: [48:06] Exactly. But there are these life principles. So you’ve probably heard this before, but you fill up this glass jar with boulders, and then stones, pebbles, sand, water. You put your most important things in your life first, and then the rest can come out. And so for me now I try to put God first—that has to be my number one—the relationship with your spouse and your kids, your health, and then work. And I look at that, and there’s a whole bunch of other things in there—service and charity that are incredibly important—but it’s hard to think, “Okay, I’m going to go change the world. I’m going to become the next Jeff Bezos or Elon Musk and have those priorities in order.” And the honest truth is I don’t need or want to be the next Jeff Bezos or Elon Musk. I respect them for what they’ve done and they are incredibly genius human beings, but I would not choose that for my life. I would prefer to choose more of a lifestyle that brings me joy and brings me closer to my family.

Joe Grover: [49:28] I love—thank you so much. There’s so much wisdom there, and you’ve been so open and vulnerable about what matters to you now and what you’ve learned through that journey. Why do you think there’s such an aversion to the word failure? Why do you think we don’t—we know it intellectually, but we don’t say it. We don’t talk about it in unvarnished ways. Why do you think that—is that pride?

Bubba Page: [49:52] Yeah, for sure. A hundred percent pride. It’s our inability to—it’s our insecurities. I’m going to go back to that. It’s our insecurities. We’re sitting here in this business podcast. I know you’ve had successes. I know the people who are listening have had successes. It’s embarrassing to say, “I failed, and here’s all the reasons why I’m a failure,” or “What I did to make this fail.” It’s hard to hear. I don’t—nobody wants to talk about it because it’s awkward.

Joe Grover: [50:20] Does it still hurt just a little bit to talk about Outro? Because it still hurts me when I have to talk about the specifics of a failed venture and the money that I lost and the decisions that I made seven years later. You and I have both been on this similar journey. I’m just getting to this point where I can even host a podcast talking about failure and actually share my experiences openly. And you’re right. It’s embarrassing. We just don’t want to acknowledge it. We want to hide from it still. And I think that’s what’s so liberating when you and I can have a conversation and be like, “Yep, we’re failed entrepreneurs, and we’re okay.”

Bubba Page: [50:55] Yeah,

Joe Grover: [50:56] We’re okay.

Bubba Page: [50:56] And we’re still alive.

Joe Grover: [50:58] Yeah, we’re still alive, and we learned, and we’re growing, but we did not hit the ball out of the park. In fact, we didn’t even get the ball into the outfield.

Bubba Page: [51:08] Nope, nope, it stayed at home plate. I feel like it’s important for those—because most people who are listening have probably failed at something. Because that’s human nature. And so if you’re listening—and something to think about—that’s part of the path. It’s part of the plan. We have to fail in order to stretch ourselves and to grow. I am embarrassed to say that it’s taken seven years for me to be able to feel like I’m just hopefully creeping out of this failed mentality and thinking more positively about myself, saying, “Okay, I can do this,” or, “I can’t,” and having that positive outlook. Even though I’m a positive person by nature, it’s been a struggle, for sure, and it’s interesting that it could—potentially a decade of my life will I attribute to having these types of feelings. And it’s not an overnight, get up the next day and you’re fine and you’re not going to think about the failure again. And I hope not. I think it’s where you can learn the most. People talk about that all the time: You learn more from your failures than you do your successes. 

Joe Grover: [52:22] We just don’t talk about it. 

Bubba Page: [52:23] We just don’t talk about it. And I would suggest if you’re not willing to talk about it yet, that you journal it, that you write it down, at least get it out. Because I think, as entrepreneurs, when somebody asks you, “How are you doing? How’s your business doing?” what do you answer? “Oh, it’s great!” 

Joe Grover: [52:39] “It’s going great!”

Bubba Page: [52:40] “Doing good! It’s great!” And you’re dying inside because you can’t make payroll. 

Joe Grover: [52:45] And we have to watch—we open up LinkedIn, and it’s post after post about—

Bubba Page: [52:49] Success.

Joe Grover: [52:50] Wins and successes and raising capital and selling businesses and acquisitions, and it’s hard to see the reality through all of that polish and varnish.

Bubba Page: [53:01] Yeah. I think realizing that everyone’s going through their own crap, whether it’s professionally or personally, every human being is going through some level of crap, some level of hell that they have to go through, and it is part of your plan. It’s why you’re on this earth. You have to go through it. Again, I’ll go back to the opposition in all things. Know that whatever you’re going through right now, it is for your good. That’s a quote, not mine. It is for your good. And you have to look and say, “Why is this for my good?” If you’re going through this depths of despair, look up and ask God, “Why? Why is this for my good? If everything that goes on in this life is for my good, then why?” And you may get some answers.

Joe Grover: [53:50] This has been a profound story and sermon today. I love it. Maybe we should rename the podcast The Entrepreneurial Therapy Session, because I feel like over the course of the next several weeks as we talk to more and more entrepreneurs—and I hope the audience feels this—we’re getting to the real root of why entrepreneurship can be so hard. And I just wonder how this experience for you has shaped the way that you invest as a venture capitalist. Now that you’ve had a failure or some, does that change the way you analyze businesses or invest in businesses? And how do you counsel entrepreneurs now, given your experience at Outro?

Bubba Page: [54:34] Well, what’s interesting is now the tides have flipped. I was embarrassed to tell my angel investors and VCs that I lost their money. I’ve now had multiple come to me and say, “Bubba, I’m so sorry, I have to shut down my business,” because I’m their angel investor or I’m their VC. And almost immediately, I try to respond with, “So-and-so, entrepreneur, I love you, it’s not your fault, and please just talk to me about your next business. Let’s see if we can do it again.” Because I received that kind of gesture, and it changed for me that mentality of who I was, and I want to do the same for others. I mean, the guy who just walked out of the room, right? I love him. This is a fellow entrepreneur. I love him to death, and I wrote the check to this entrepreneur because I love him, and I believe in him. And even though the business didn’t work, I still love him as an individual. He’s a good human being. And yes, 50 grand is gone, and that’s part of investing, and I get it. And now, from this side, I can see how my investors felt when mine didn’t work. And it has healed a part of me, because I know that they’re just like, “Hey, you know what? You win some, you lose some. I was hoping, but I get it, and it’s okay.” 

[56:04] So I don’t know. I feel like as young entrepreneurs, if you’re listening to this, don’t get discouraged about not starting because of failure. I think that’s where most wantrepreneurs end up is they have these ideas, they think they’re genius ideas, and then they never execute. Execution is really the key to success. You may want to fail faster, though—the concept of failing fast they teach in Techstars. Fail fast so that you can essentially pivot or iterate and change to find what might work. The faster that you can make those iterations—and Sam Altman, the founder of OpenAI, who also led Y Combinator for a long time, he says the companies who iterate the fastest will have the most success. If you’re uploading your new software every month because that’s your cadence to go live, and another company is doing every two or three days, think of how many iterations they get over you. And those companies will see more success.

[57:10] So I would look at you in the eye and say, “Still go for that idea, but fail fast.” Don’t draw out the process to take two or three years. Try to find out as fast as you possibly can if it’s a viable idea or not. That means don’t talk to your mom or your grandma or your aunts and uncles. Go talk to random strangers. Give them the product or let them use the tool. Or even, if you don’t even have it built, go try and presell whatever you’re going to do and see if people are willing to do it before you go and spend years and years of your life on something you may not know they want. 

Bubba Page: [57:51] I’m Bubba Page. I’m the founder of Outro.com, the company that failed. Raised venture capital, spent two and a half years of blood, sweat, and tears. We had to shut it down. But don’t get down, because you can do it over and over again, and at some point, that success will come. So keep at it.

Joe Grover: [58:08] Thanks for tuning in to The Real F Word. The real F word is failure, and remember that failure is a stepping stone; it’s not just a stumbling block. Join us next time as we continue to explore the journey of resilience and growth, without ignoring the true costs personally, professionally, and financially that comes with failure. Keep learning, keep growing, and keep embracing the real stories of entrepreneurship. See you next time.