Entrepreneur Zak Waddell: Startup Lessons and The Bachelorette Experience

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My guest for Episode #214 of the My Favorite Mistake podcast is Zak Waddell. He’s a college success manager at Woolf — the first global, collegiate higher education institution allowing membership for qualified new colleges through their software platform.

A previous guest, Anthony Trucks, (Episode 97) was a contestant on American Ninja Warrior. Zak was a contestant on a show that might be even more grueling (at least mentally): The Bachelorette (Season 9)

In this episode, Zak shares his favorite mistake story about, as an entrepreneur, falling in love with a business idea instead of starting with the “voice of the customer” and their needs. In this startup, why was it so difficult to challenge the traditional commission-based real estate model? What assumptions turned out not to be true? What did Zak learn? How does the experience with that failed startup help him now?

We also discuss his experience as a contestant on The Bachelorette. Did he ever think it was a mistake to start that journey? What mistakes do contestants make? What mistakes might viewers make when watching a “reality” show? We talk about that and more in this most dramatic episode of My Favorite Mistake yet.

Questions and Topics:

• Falling in love with an idea
• Need to take a Iterative approach and listening to customers
• What assumptions did you have to test?
• What did you learn through cycles of learning…
• Pivot or Pull the Plug??
• Not vetting individuals… not stopping to think if it was the RIGHT team…
• How to manage in less hierarchical ways?
• Failed startup — really helped him for what he’s doing now
• Rigorous iteration — failing fast, failing forward
• Applying those lessons to future ventures or Woolf?
• The Bachelorette — Was there any point when you felt like it was a mistake to sign up for this — before or during?
• Do you try to learn from previous seasons or just do your own thing?
• Why does it backfire when a contestant tries to report bad behavior to the Bachelorette?
• A mistake as a viewer to think what you see is naturally occurring vs. stirred up by producers? And editors?
• Is it by design that more couples from the show are getting married now?
• Tried to apply entrepreneurship concepts on the show? Fall fast, fail often?
• If asked to write a book about the lessons from the show for business?

Scroll down to find:

• Video of the episode
• Quotes
• How to subscribe
• Full transcript

Find Zak on social media:

• LinkedIn
• Instagram
• Twitter

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Transcript:

[background music]

Mark Graban: Episode 214. Zak Waddell, customer success manager at Woolf and former contestant on “The Bachelorette.”

Zak Waddell: In the entrepreneurial space, learning that the idea means nothing, it's all about the execution.

Mark: I'm Mark Graban, this is “My Favorite Mistake.” In this podcast, you'll hear business leaders and other really interesting people talking about their favorite mistakes because we all make mistakes. What matters is learning from our mistakes instead of repeating them over and over again.

This is the place for honest reflection and conversation, personal growth and professional success. Visit our website at myfavoritemistakepodcast.com. For links and more information, look in the show notes or go to markgraban.com/mistake214.

Hi, I'm Mark Graban and welcome to the most dramatic episode ever on My Favorite Mistake. My guest today is Zak Waddell. He is a customer success manager at Woolf.

They are the first global collegiate higher education institution that allows membership for qualified new colleges through their software platform. We'll talk a little bit about that business and other entrepreneurial ventures from Zak's career. The other thing I'll mention is, you may know from the way I introduced this episode.

First off, episode 97, Anthony Trucks, who was my guest, he had previously been a contestant on “American Ninja Warrior.” Zak Waddell, joining us today was a contestant on a show that might be even more grueling. That show is The Bachelorette. Zak, sorry for the tortured introduction there. How are you?

Zak: Hey, not a torture at all, that was fun. Well done. Bravo.

Mark: [laughs] My wife is a huge fan of the show, so I've picked up some of the lingo and some of that along the way.

Zak: A lot of it feels like climbing a warped wall, just like Ninja Warrior. Good analogy.

Mark: I hope you didn't come away with too many bruises.

Zak: No. It's interesting experience being thrown to the fire and seeing how you come out forged or unforged. It's a good exercise in creating your own narrative and controlling your own narrative throughout the show. I came out OK. Others didn't, but I enjoyed it.

Mark: All right. Well, we'll come back to that later on because I think in terms of the question we normally start with, I think your story is something not related to that. Thinking about rocky ups and downs, challenges, and entrepreneurship. Let me get back to the question at hand, Zak. Of the different things you've done, what would you say is your favorite mistake?

Zak: It's funny. A little bit of a circuitious way to answer this. When I thought back on my favorite mistake, I thought about a story my grandfather used to tell me. He talks about his father coming from Croatia to the New World, and three brothers.

Anyway, two of the brothers, including my great grandfather, got on the boat to Ellis Island, but the other brother somehow didn't make the trip. Years later, they hear from him via whatever method they do, but he'd ended up on the wrong boat and ended up in Chile, carrying the root stock from their family vineyard in Croatia.

From my grandfather's point of view, this was always a story of foreboding, like, “Be on time. Be responsible.” We find out years later that there's this other lost Chilean individual. He started a successful vineyard. To this day, it's one of the higher-end boutique vineyards in Chile.

For me, it flipped it on its head. Someone that either by mistake or by design got on the wrong ship and ended up having a really great…The mistake turned into a really great opportunity.

Mark: That happens sometimes. We can be thankful for that when it does.

Zak: For me, I'll come back to my story, I had a long transition falling in love with ideas, and in the entrepreneurial space, learning that the idea really means nothing. It's all about the execution. The way in which you execute is that true iterative approach, going out, listening to the customers.

Even though that was built in the game plan for me, surrounding yourself with other founders that think the same way is so important. That was my big mistake.

Mark: Maybe first off, if you can give the example of the story you're thinking of here, what the idea was, what the company was, if you could unpack that a little bit.

Zak: Sure. I think at the time, I come from an entrepreneurial background. My father was an entrepreneur. Various degrees of successes and failures, as most entrepreneurs have, but I was in a position working for a large Fortune 2000 company that was going under. The ship was sinking.

A lot of us were coming up with ideas of what's next. The markets weren't great. The job opportunities weren't great. I had some ideas I'd been working on for a while to start something new. Now, the people I were voicing these ideas to were people I worked at as an organization. They were all falling with the ship. They said, “Let's do this.”

My first — unpacking that — big mistake was not really vetting those individuals. It was mostly out of necessity that we came together. We didn't really have time to take a breath and say, “Is this the right group?”

Mark: Were they the right individuals because they had certain functional or technical skills?

[crosstalk]

Mark: Are you talking about that in terms of like shared values or approach to entrepreneurship?

Zak: I think that's it. When you're the one that's been mulling over these ideas and building them for months, and even years, in this case, all that you've put into it comes across as, “Hey, this sounds exciting,” but the ideas that were the backbone of it, for me, were things like distributed leadership, new ways of approaching management in a way that wasn't as hierarchical. That was a big part of it.

I had put together hundred, not hundreds, but large governance docs that nobody really took the time to read or understand. That was also my fault on the execution of not like, “Hey, foregrounding this, let's all read this together and make sure we understand it.”

Mark: Sure. Tell us about the idea of the company and how that got started. Maybe we can come back and talk more about like the culture and the people side. Is that OK?

Zak: Sure. The company itself was in flat-fee real estate. There were very few companies at the time, and they were mostly very regionally located. My idea was to start a flat-fee commission real estate company that was based on your social network. People that you potentially know or trust to do the real estate transaction for a set flat fee.

We all know that cousins, aunts, and uncles, a lot of them have a real estate license and just aren't using it. If you can find someone to do the transaction for $3000, $4000, everybody comes out ahead.

Mark: That's certainly appealing compared to paying six percent, which is pretty standard. It's interesting how industries have these standard fees. Was it appealing to both sides of the transaction? Let me ask it this way. What assumptions did you have to test to see if that would fly?

Zak: Good question. Of course, it appeals to anyone. The disparity between the six percent and the flat fee not only is a lot easier to palette, but also when it comes down to the brass tacks of it all, it's difficult.

What I wasn't really factoring in was the difficulty of moving realtors that are full-time realtors away from that model, no matter if there's a personal relationship involved or not. I realized pretty quickly that the way to test this was to go out and become a realtor myself. Go out and start using my own network to test.

The disparity that was with the other founders was not everybody wanted to go out and do that. That's where it started to break apart.

Mark: Then what kind of cycles of learning were there then at least for you going out and putting that license to use trying to test this model?

Zak: Again, it was easy to tell the story and it was easy for people to buy in and understand the idea, but it was a lot more difficult breaking from the patterns of behavior within the real estate market, also within the regulatory framework. There's some states that didn't even allow this to happen.

That was a big barrier that I had scratched the surface on in my research, but not fully dived into it. That's when it became apparent how difficult it was going to be to break the tradition.

Mark: Then I'm curious, when you start seeing barriers like this, some of them very entrenched, very systemic, was there a thought process of trying to find a way to pivot or pulling the plug and saying, “Well, we tried. We learned some things. There's no shame in that. Life goes on”? How do you weigh some of that decision then?

Zak: Really good question. For me, having fallen in love with the idea of what I wanted the business to be, it was something that I found meaning in doing or bust. The pivot idea, which where it turned, was something that I wasn't as interested in being a part of. That's when I made the departure.

The company, to my knowledge, is still around. I think they're doing some reverse mortgage type of thing, which is not the direction I originally wanted it to go. Those pivots are essential if you're in it for the long run. For me, it was more motivated for mission, and that's where I departed.

Mark: I'd like to come back then. You talked about some of the people dynamic of did you have a team that was aligned with your view of how you wanted the company to be managed?

I was wondering for one, if you could just talk a little bit more about your thoughts and inspiration around being less hierarchical. What influences you had on that and what you would have wanted to see in the company had it gone the way you would have hoped.

Zak: I can think back at time, I was reading a lot of this Apple stuff, the Inspiro Group out of New Zealand. I was deep into that and saw the path towards a better way, but only in the way the stories were being told, not in the execution of it.

I tried to put together, like I said, my own governance docs that were informed by what I was reading, but I never really had those powwows with others, members of the leadership team to say, “Hey, let's make this work. Let's understand it together. Let's riff on it a little bit.”

It was just like, “Hey, it's sitting in my folder in my Google Drive somewhere, and I'm silently trying to manage by it.”

Mark: Is it fair to say of all the things a startup is trying to do or figure out, “How do we prioritize? Are we finding product market fit? Are we having to adjust? What experiments are we doing? Are we developing whatever platform you were maybe developing?”

I could see where stopping the talk about culture might sometimes feel like a luxury or not top priority for the others.

Zak: Yeah, I think so. To be fair, it probably wasn't at the time. When I talk about the mistake, one of my big mistakes is trying to push that agenda too early. At the end of the day, when I think back, was I in love with like, starting a company or just starting a company that looked like this? I think that was it.

It was this vision of coming out of a large corporate hierarchical structure, “Hey, here's an alternative. I want to make an alternative come to life.”

Mark: In some of my own career path, I've vacillated or swung back and forth like a pendulum. I've made mistakes of over-adjusting sometimes, of leaving big corporate life to go to a startup and then tiring of the problems that came from that.

I probably made a mistake in swinging back to corporate life again.

[laughter]

Mark: A mistake I will probably not repeat again. I'm sure I'm unhirable at this point. Maybe we can transition to talking about, Zak, what you've seen in terms of lessons learned, future ventures, or even of being applied to what you're doing through Woolf.

Zak: It was an eye-opening experience for me to understand the need for good mentorship and leadership. Being around someone that was a lot smarter than I was, that was a lot more grounded than I was, that was about execution and could execute in ways I couldn't before.

It's just been so great to take a backseat to these dreams of becoming a lead and just saying, “I'm happy being second fiddle to people that are way smarter than me. Then I can fit in a place, do my job well, but still be a part of an entrepreneurial venture that's actually going somewhere.”

Mark: What stage was Woolf at when you joined? Would you say they had already found product market fit in its definition of their platform for different colleges and universities?

Zak: Yeah. It was on the second or third iteration of product market fit. Not to the way we've seen success recently, but I was probably in the what, first 10 employees out. They started to slowly grow to where we're 50 or 60 now.

At that point, it was coming off of an early stage, like building a license or a portfolio of accreditation licenses globally. As that portfolio started to build, it was about finding the right customers, colleges that wanted to start using those licenses. When I started, there were less than…Let's see, probably less than 10 colleges. We're at close to 30 now.

These colleges that we have now are substantially larger than when I started off. It's been a good ride.

Mark: Then are there opportunities in your role as a customer success manager to at least practice in different ways these principles around iteration, and learning, and some people would say failing forward? It's not my favorite phrase. I don't know why it came to mind. Other ways to apply it now in the type of role that you're in.

Zak: Because this field of accreditation management and accredited learning outside the scope of a traditional university setting, brick and mortar, I should say, is so new, I think we're all willing to make those small mistakes, fail quickly, learn collaboratively, and throw egos out the window in a way that doesn't exist in the traditional pathways.

That part's really great. When you sit with a new college founder that has had a lot of success maybe at a university, is branching off on their own, starting a college, provides extremely high-quality education, but needs to find a venue to do that. This new college setting is just really exciting. Finding where the students are is a process that changes every day.

Mark: Not knowing the market that you're serving and working with, it's a little surprising to hear of new colleges and colleges being started. It seems like you hear more often of struggles of older, smaller schools. I'm curious what your perspectives are in terms of startups, I guess, in a way.

A startup college and the challenges they're facing, the question I was going to ask them was a little bit about Woolf. If somebody's starting a college and what services are they getting from Woolf that they might not have to build independently?

Zak: As an example, you can think of a large boot camp maybe in India that has thousands of students signing on every single month that are providing cutting-edge education in ways that traditional universities aren't encoding, but specifically encoding in areas that are employable.

All of the latest coding languages are taught to in real time as they're emerging with high-quality instructors that are coming out of some of the top Indian universities. If they were going to go the traditional path of getting this accredited learning inside a university, the licensing process will take years.

Because we're able to move so swiftly and nimbly outside of that environment, we can spin up these new colleges with these same high-quality professors, add some elements of peer-reviewed literature and all that's required in a real academic setting and come out with the same ECTS-accredited degrees that students are getting coming out of Oxford or University of London.

The same qualifications, but do it. The accreditation part is much faster and much more.

Mark: That's interesting. It's not a matter of outsourcing certain functions, it's really more of a time to market.

Zak: Time to market. These colleges could go down the route, I assume, or I know of filing for their accreditation. Again, that process takes many years on their own, and it requires a number of individual, whole team and department at a high headcount.

In our cert, we essentially take over that responsibility and say, “Hey, here's our licenses and our portfolio, use what you can teach to and then you grow your business as you see fit without worrying about the accreditation piece.”

Mark: OK. Cool. All right. You talked earlier about falling in love with an idea. Let's talk The Bachelorette. Now, I'm going to share just a preface. Zak and I first…When did we first meet? Like seven years ago?

Zak: Yeah, that sounds right.

Mark. We share some professional certification and interests around continuous improvement methodologies. There in the DFW area, there was this opportunity to meet, networking, compare notes, and we're sitting there having breakfast, I think it was, and sharing my background and Zak's going through his career. Then casually throws out like, “Oh, then I was on The Bachelorette.”

[laughter]

Mark: Just kind of slipped that in there which I said, I get a sense of the show, but I didn't recognize you from the show. When I came home and mentioned you to my wife and to her mother they were like, “Oh, Zak, we love Zak.” That was my introduction to you back then, at least.

Zak: It's funny, the audience of that show, you never know who's watching. I remember at the height of viewership when I was coming up…I was still working in oil and gas, and I would be down in South Texas at a small town at a gas station. Guy coming in in boots and a cowboy hat, “Hey, aren't you that guy from ‘The Bachelor'?”

[laughter]

Zak: It's crazy the reach that show has.

Mark: I will admit to being drawn. I think especially pandemic times, I got drawn into a couple of seasons where I was watching probably as actively as Amy, but she's still with it and watching the new seasons. I'm curious to hear the decision process of applying to be on a show like this and wondering, is this a good idea?

Is this a mistake? Or what did you think? No. How much did you try to evaluate that, or did you just dive into it?

Zak: It's a very similar situation to starting the startup in the fact that the alignment was right. In the case of the startup, the company I was working for was failing. We all knew we were going to be cut.

This time, I was living in San Antonio working in oil and gas. I was having a really hard time meeting people. I didn't have a lot to lose. My sister would say, “You should try out for the show.” I tried out, didn't think much about it.

When I got on, the risk was you're gone for a couple of months, you travel the world, you get to hang out with other cool guys on the show. Some not so cool. What do you have to lose? You may meet someone exceptional.

What you have to lose is the possibility…At the time, I was a consultant in oil and gas. I was able to move from a project and then come back hoping to find another, but didn't have a lot to risk at the time.

Mark: Then as my wife had pointed out, as she knew, “Oh, Zak's sister, Carly.” She had been one of the women on a season of The Bachelor before you, right?

Zak: Actually, after.

Mark: After. Sorry.

Zak: No, it's OK. During my show, the film crew had come to meet my family because The Bachelorette was coming to my house. They met my sister and they said, “Oh, you should come on the show. You'd be really great,” but the bachelor for her season was going to be somebody from mine. Usually, it's somebody within that pool.

We already had a good idea of who it was going to be. It was somebody that she wasn't too fond of. She obviously delayed her being a contestant on the show for another year and rolled the dice. It worked out. She ended up being on two additional spin-offs of the show and got married from it.

[laughter]

Mark: My wife's going to cringe when she hears me make the mistake of who was on first. My mistake, so it goes. Was she able to benefit from your experience at all or did she do her thing her way?

Zak: The funny thing in terms of benefiting from the show that didn't exist when I was on was the prevalence of social media and influencer culture. It was just starting to take root.

By the time my sister was on it two years later, the people that made it in the top five or so from the show who got a good audience base could essentially make a living from it, as we know what influencers are now. She really continues to do that even to this day.

Mark: What year was it that you were on?

Zak: Let's see. 10 years ago.

Mark: That was not one of the very first seasons. It had already been established and been around for a while at that point.

Zak: That's right.

Mark: I'm curious for you or if you had a sense from others. How much do you go and study previous seasons and try to figure out what to do or is that maybe a waste of time, you need to just come be yourself and do your own thing?

Zak: For me, I knew I would lose motivation if I watched the old seasons.

[laughter]

Zak: I purposely didn't and went on having everything be fresh and new.

Mark: Did you get a sense from the other guys who you were competing with on that season? I imagine some of them. I'm not sure. It's different approaches. Some probably broke it down like game film and seriously studied it. Some were like, “Hey, wait. Oh, there's cameras? What?”

Zak: I think those who studied, it was detrimental. You tried to employ certain strategies that you'd seen four seasons ago. Others had picked up on those strategies being reemployed. The show would essentially foreground anything that was similar. They would spotlight in a way that you know it was going to cause drama.

My whole strategy was essentially just sit back and don't get involved in any of the drama. That worked out well.

Mark: You were trying to head off that you predicted that would have been a mistake.

Zak: Predicted it would have been a mistake, absolutely.

Mark: It's such a fascinating dynamic to try to think what…It's one thing to watch the show, then it's another thing to step back and try to put yourself in the shoes of somebody who was going through that.

First off, though, I think there's a general business or career lesson there of don't try too hard to copy what some other company did. At some point, you've got to be yourself and do your own thing.

Zak: No, I think you're right. The interesting thing about the experience was there's a person that's put up on a pedestal that you don't know a lot about. You have the hope at least that they're somebody exceptional because they were put on that platform. Then it's all about finding out if they are.

You get very limited data. One week, you spend 5 or 10 minutes. As the show goes on, you get to spend a little more time, but it's never more than a couple hours in a week. That's all the data you have to go from.

Mark: Wow.

Zak: Your hope is that you get to the end, and now you have exclusive time to figure it out. In order to get that exclusive time, you have to really wait it out. [laughs]

Mark: Everyone's taking a flyer of what path is going to happen. I'm sure there's different things that happen where one of the other guys right away…What was the bachelorette's name for your season?

Zak: Desiree.

Mark: Desiree. That some guys might come in and whatever, and right away think “OK, well, no, there's something about Desiree just not attractive to me. It doesn't seem like a fit.” They might think that right away. Then OK, well, maybe they're just destined to have a short stint. They get sent home in the first group. Maybe that's for the best.

Then there's probably others who at the other extreme, at the other side of the spectrum are like, “Oh, she's amazing.” You have attraction and feelings, and you're trying to pursue that. Then there's that middle ground where it seems like there's people on each season who just want to be on TV.

There's this question or this conflict of they might not be into her, but they want to stay around. What are your thoughts on that dynamic from what you experienced or as you see perhaps other seasons of this?

Zak: A couple things. One, it's even more prevalent now because people can monetize their time on TV. That adds a whole another layer. In my time, it wasn't as prevalent, but you have those people that maybe are between jobs, maybe don't have a lot going for them in a career. This is just time to hang out. It's not even about being on TV, it's just like, “I have nothing else to do.”

[laughter]

Zak: That adds a complexity to it because those individuals, from my experience, tended to cause drama.

Mark: The different types of mistakes. You mentioned people trying to follow someone else's game plan. I'd say here, I'm going to ask you this because I've seen enough of the show to know this never seems to pan out well.

You can see a mistake coming, where let's say, I'll frame it in terms of a Bachelorette season, where one of the guys is really behaving badly, being rude to everybody else, even being disparaging towards the bachelorette. This is bad, but then one of the other contestants decides, “Well, I need to go tell the bachelorette what's going on.” That always seems to backfire.

Zak: Exactly. Even let's say Person A has gone and told the bachelorette. You have a conversation with her in two hours and you don't really want to bring it up, either. She's heard it from everyone else. It's been a topic of conversation. She understands that part of the allure of the show is this this drama sub-thread. That has to happen.

Through sometimes the stimulation of the production crew, they'll throw in a question. Then all of a sudden, you find yourself talking about it even though you didn't want to. There is that artificial aspect of it. Even comes to it more in the editing.

Mark: I was going to ask about those maybe three pieces there of the artificial nature of who the producers are selecting. You can always tell. There's certain types of like, “Oh, there's the troublemaker.” Then, “Oh, that person's a train wreck.” There's that.

Then there's what the producers might try to instigate and then the way that it's edited. How do you think those three pieces contribute to this “reality television” maybe not being that real?

Zak: No, that's certainly their magic formula. Like you said, there's the certain archetypes that will always be built into the casting. There is this element of interceding in situations to create the drama, and even more so, wearing you down into saying something.

Every day, you're called in for probably an hour-long, one-on-one interview with a producer, sometimes twice or three times a day. Their whole goal is to get snippets, little sound bites they can use. I took the approach of not giving into it and controlling my own narrative, essentially.

Others don't. They'll have too much to drink or they'll be weak-minded enough to let everything spew out. Then the editing part is the element you really have no control over. You can be made to be a hero or a villain.

Mark: Going through that, at some point, you say, “Well, I'm going to do my best. I can only control how I act. How they're going to portray it, that's part of the risk of coming on a show like that.

Zak: That's right. You can only control so much. That's for sure.

Mark: If somebody came to you and said, “Hey, Zak, I'm thinking about going on this.” Do you have blanket advice of either run away, or, “Hey, if you want, go and do it.” What advice might you give to someone who's…Because the show is still going on. They still want people to apply.

Zak: To me, it's completely a risk-reward thing. If you have a lot going in your career, with friend groups, and all these things that you're happy and content with, then take the long path in trying to meet someone special.

If you don't have a lot going on, then maybe the…There is this element that because you have some exposure, that you do have a chance of meeting someone after the show, which is an element that I think a lot of people consider.

To me, it completely comes down to career. If you've got something going for you, if you're going to take three months off, the job's probably not going to be the same when you come back. You're going to be pushed out in some capacity. Don't take that risk if you have something going for you.

Mark: What was the time frame again? If someone goes, gets sent home right away, that's how much time between arriving and departing? Real lifetime, not TV time.

Zak: That's right. I think the shortest you can be gone is probably a week. If you get sent home on that very first rose ceremony night, you spend about three or four days in a hotel with the pre-production stuff. Then you probably have a day after of production and then you'd be sent home.

In the most extreme example, you'd be gone three months if you made it to the final. A whole three months.

Mark: Then, you finished fourth place in that season. You made it pretty far to the end. For people who don't know you and your story, if you wouldn't mind just walking through a little bit about how The Bachelor ended and then meeting your now wife that you have a family with.

Zak: Good question. It was interesting. I was probably strung along with other contestants. In terms of ending, I don't think you ever see it coming when you get to those later stages that you're going to be kicked off. When I was, I was kind of shocked. I didn't think I would make it to the end, but I thought at least I would get one step further.

You're looking at, you're like, “That guy made it?” It's one of those things.

Mark: I'm not going to ask you which guy you're referring. Maybe some other time.

Zak: That was the only shocking part. In terms of your on-camera reaction, there is a sense of responsibility you feel at that point, no matter how you feel, to show it up a little more than maybe what's inside. I'm sure everybody feels this, but part of it is out of duty and respect for the bachelorette in some way.

You don't want to come across as, “OK, fine. I'm going home.” It's a little bit disrespectful for the real or simulated relationship that you've been in, right? There's that. Coming home, you're in this weird about two-month period between leaving the show and the show airing.

They scare you with all these clauses. “Hey, you've signed here. If you talk about the results, you're going to get sued for whatever, two million or three million or something.”

To make that even more complicated, at the time I was being told, “Hey, you're the favorite to become the next bachelor.” I'm sure other people are being told the same thing. “You better be good, you better sit by your phone because we may be calling you at any time.”

Luckily, I had a good friend from the show that him and I spent a lot of time with, and he was being told the same thing. He ended up being The Bachelor, but I ended up meeting my wife, Elizabeth, during that period where I was…

When I met her, I was like, “OK, even if I got the call, I don't know if I would take it.” It was a pretty easy decision when I met her. I was obviously really interested in meeting someone special, and then meeting her was a no brainer. The timing was right, and we jumped into it.

Mark: Now, it's one thing for Desiree and who? Sorry. I don't know the names, I should have done some research here.

Zak: No, Chris.

Mark: Chatting about this. Chris. Desiree and Chris, it's one thing that if they're still together, they have to try to keep that under wraps or quiet, or no. For you, I don't know. Did you think like, someone's going to see you out with Elizabeth and take pictures and say, “No, Zak didn't win?”

Zak: Yeah. At that point, I kind of didn't care.

[laughter]

Zak: It was, I would be held responsible for the things I said, not as much being in a picture with someone. I was fine having that happen. It's funny. All that being said, when everything was revealed, we would go on couples trips with Desiree and Chris and my wife and I think even before we were married.

The interesting thing was, the friendships were there between all of us, but you could tell the romantic connections weren't as much as we were making them out to be at the time. It was interesting to see how that all settles in that period.

Mark: Things work out for different people in different ways and different paths. It's interesting to see. Sadly, I don't know the exact percentages, but it seems like…Especially in earlier seasons of The Bachelor and The Bachelorette, the percentage of couples that actually went through with getting married was very low.

Ryan and Trista from a season, and then it seems like there's been more of that recently. I don't know if that's something the producers…because they seem to want to bank on, this isn't just a game show, people are getting engaged and married and having happy lives together. It seems like that's happening more.

I don't know if that's by design or if there's other factors, I wonder.

Zak: I think it's by design and the fact that they will create this fairy tale Hollywood TV wedding for you if…You get all that comes along with that. That will be granted, for TV. Then the divorces that happen afterwards fall by the wayside, which are just as prevalent.

Mark: One other question I was going to ask just about some of those dynamics, you mentioned going on trips with other couples. Do you feel like there's a fraternity/sorority of people who've been on the show?

Maybe it is very much like a fraternity and a sorority. That guys like you who are contestants on The Bachelorette season, in a way you, have a lot in common with the women who are competing for The Bachelor. Is there a community or a formal way, or you've got some people that you've met and you're friends with?

Zak: Absolutely, especially for the time right after the show. While people are still single, they all benefit from banding together and being a part of that community, that fraternity, publicly to attract for long-term relationships or short-term relationships, but there's certainly that benefit to it.

I've noticed that as people like myself get married and settled into family life, those fraternities start to break apart in a way that…

Mark: There we go. Different stages of life. Sometimes you don't get to keep in close contact with your college buddies, whether it was fraternity or otherwise. It's fascinating to talk about these different aspects of entrepreneurship and The Bachelorette. Thinking of taking risks, evaluating risk, heading off mistakes, bouncing back from mistakes.

We're drawing connections there. I'm going to put you in the spot. If someone were to say, “Hey, Zak, we want you to write a business book about entrepreneurship lessons from The Bachelor or The Bachelorette, is there anything that comes to mind?” We can always brainstorm on a title later.

I'm totally putting you on the spot, but anything that comes to mind there? If someone were to say, “Hey, we're going to dangle this book contract in front of you,” what would you say?

Zak: I would say don't read my book, write your own book in real-time conversation with others. I think to me, more and more, I'm realizing that's where the real knowledge is. It's just being engaged in the process of knowledge creation in real time as the world is changing.

Don't be afraid to say the wrong thing, do the wrong thing, but be in conversation and community with others where it's OK to fail.

Mark: That's very well said. I think that's a great note to end on there, Zak. Well done. Thank you for coming on and suffering through my semi-informed questions about the show.

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Mark: Thanks for sharing your favorite mistakes story, and more importantly, lessons learned, and being open about that. I really appreciate it.

Zak: Of course. Always great to talk to you. Enjoyed this.

Mark: Likewise. Thanks, Zak. Thanks again to Zak Waddell for a really unique and interesting discussion here. For more information about Woolf and more, look in the show notes or go to markgraban.com/mistake214.

As always, I want to thank you for listening. I hope this podcast inspires you to reflect on your own mistakes, how you can learn from them or turn them into a positive.

I've had listeners tell me they started being more open and honest about mistakes in their work. They're trying to create a workplace culture where it's safe to speak up about problems because that leads to more improvement and better business results.

If you have feedback or a story to share, you can email me, myfavoritemistakepodcast@Gmail.com. Again, our website is myfavoritemistakepodcast.com.

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