My Favourite Failure: In 24 hours I went from leading the rocketship to the gig being over, in my own company - Adam Weber

0:00Let me ask you a question. If someone wanted to access your company's devices or premises, how difficult would it be? If they had a helping hand on the inside, could they get it done? The answer is probably yes, which is why we're working with the National Protective Security Authority and the National Cybersecurity Center to share their secure innovation campaign. They can see that state actors, as well as competitors and criminals, are looking to steal from UK startups. You're probably aware that your cybersecurity needs to be rock solid, but a lot of startups forget about insider risk. Take one company the NPSA told us about who had a disgruntled member of staff.

0:38A state actor charmed them into stealing the company's flagship software, which they then took to the state-owned business instead, costing the company billions. If you want to get a better handle on your security, the Secure Innovation campaign can help. Check out npsa.gov.uk forward slash innovation and download their free quick start guide. There's a link in the show notes. I don't want to dismiss the level of pain that that was for me and the level of also the ego damage that like my overly inflated ego was was forever changed by that. And it took me it didn't take me two weeks to get over that.

1:22It took it took it's it's taken me years. Adam Weber is a multi-exited founder, podcaster and the SVP of Community for 15.5, a performance management software company. What's fascinating about Adam is he ended up making it in a very different role to what he thought he was good at and to the role he thought he was going to spend his career mastering. Adam had been a salesman until the biggest deal of his life collapsed along with the plan for his future.

1:55Adam was the co-founder of an employee engagement SaaS business called Amplify. He was leading sales, and the company was growing like founders dream of. They crossed$5 million ARR quickly, raised the Series B, and had 75 staff. They were going to be one of those companies that people case-studied, and Adam was close to signing a deal to end all deals. You know, I'd had a quarter that was really exceptional for us. It was the best quarter we'd ever had. And we had this, I'll never forget the thing I shared with you in the email. It was like the night before, we were short a goal. We were 80 % of this really aggressive target that we had.

2:34And I had this deal that I'd been working for a year. It was for a million dollars in recurring revenue. So massive deal for our company. Our average deal was$25 ,000. This is massive. Had been working on it for almost a year, flown to Canada several times. And paperwork's all agreed to. It's already redlined. It's sitting in front of the CEO. And at 10 p.m. that night, the CEO goes, no, I don't want to do this anymore. I couldn't have seen it coming less. And so I went from thinking I'm walking into a board meeting with all the swagger in the world. Like, I am one of the very best of this whole, you know, and the experience was very different than that.

3:15You know, I was super discouraged about losing such a significant deal that I'd spent so much time on. I ended up being short of goal when I thought I was going to triple the goal or basically double the goal. And so, yeah, it was a pretty humbling and eye-opening moment for me. And then what happened after was really interesting. As part of the Series B and part of our natural growth, the board had really decided that it was time to switch from founder-led sales to hiring an outside VP of sales. So all in one 24 hour period, I went from thinking I was like on the rocket ship, VP of sales track to kind of like, oh, it's over from my own company.

4:00You know, and I'd say that was definitely the most transformative day of my career, I'd say. It was difficult for Adam to keep a grip on reality, on his identity. The biggest thing was disorientation. I just felt disoriented. I had to reconstruct and it took a lot more than 24 hours, my own dream of my career. Because I had to kind of decide like, cause they were also like, you're super valuable to this business. We're not asking you to leave. We just want to bring in a VP. But in my head, I actually was like, no, I am a VP of sales. That is my identity. And I'm not quite ready to shed that identity.

4:38I wasn't ready to shed that identity yet. And so I was just trying. It was some some version of for the last eight years, feeling like you were the greatest thing since sliced bread. Everybody telling you all these positive things about you and telling you you're doing so well to then just immediately getting other feedback. Right. And so it was a really jarring experience for me. And I also just had no clarity on what might be on the other side in the moment. I was just disoriented. In his moment of need, Adam did something I'm a massive fan of, something I try to do every year, although admittedly on a smaller scale.

5:21My business partner, Santiago, he was familiar with this company called Reboot, and they do retreats and quests, vision quests is what they're called, for founders who are burnt out and kind of in disorientation. And he was already familiar with the organization. He's like, hey, what do you think about going on this trip? It's 10 days out in the wilderness and where there's other there's kind of people who are experts to kind of talk about your past, your childhood. Why did you become an entrepreneur? Why did you get into the sales side of entrepreneurship? And then there was a four day period where I was just like alone by myself in the wilderness.

5:59I mean, it was a water only fast for 48 hours by myself in a grizzly bear country, which I know sounds kind of wild, right? But they, um, every day you kind of like, I was journaling. I kind of went in with the intention of like, I want to know what's next for me and I want to have clarity on what's next. Um, and it was those four days were, and I know it might not be realistic for folks to give themselves that long a time, 10 days to really process. Right. But what happened to me during the four days alone was that last night after kind of like thinking about why I started a business in general and why was I in sales?

6:38Was it actually about a love of sales or was it about financial insecurity that I had in my own life that I hadn't resolved? Why did I start an engagement company in the first place? Was it to make a whole bunch of money or was it because this was a topic that I actually think I could most influence the world in? And I kind of had all of these things come together. And on that last night, I remember writing like, oh, I started this for me and everybody, all of us that started the company, There are three of us like our version, why we started the company was different. But for me, it was because this is my topic and I and I have a and I have something to share on this topic.

7:13And so I kind of came out of that and had clarity. I became the chief people officer actually like on the flight home. I Santiago was with me on that trip, but we literally shook hands on the airplane. And and one of the last things that kind of the group that was there, the leader of that group said, but he was like, I think this is a time for you to find your own voice and to be confident in your voice. And I just look back at that moment of a guy who thought he was a VP of sales, thought that was his entire identity to then in rapid succession, like totally changing the trajectory of my career.

7:50I wrote a book within three months of that about leadership and culture. That book unlocked all sorts of things for me. And then today, now all I do is talk about culture, leadership. I've got a podcast. And so it's a, it was like something I would have never, I don't think I would have had the courage to ask myself, like, is this what I want? Like, is the sales path what I want? But that failure moment, and it was my failure that created it, by the way, like, right, I did not hit the goal. And, but it was that failure moment that actually clarified for me, like, this isn't actually for me, the journey that I want to be on.

8:28Adam thinks it's about finding work that's in alignment with your natural energy and he easily could have gone his whole career without discovering his own alignment if it hadn't been for this egg on face experience I used to every single morning before I even checked my email the first thing I would do is check my retirement account and and the reason why I did it was because deep down what I what I kind of realized was I was thinking to myself how much longer do I have to do this? Like this is, it wasn't sustainable. And my body knew it wasn't sustainable. That's why I was doing that. Whereas, and then, and then kind of flipping that to work that is in alignment where you go, I'm not looking for an end, right?

9:13Like this is just my work to do. And I just want to do the work. It's just, it's a really interesting, it was a really interesting shift that I would have had no idea. Adam is keenly aware that as a founder, you have to wear many hats. You often have to do work which isn't in alignment with your energy or talents. So he designs his life outside of work in a way that ensures he can deliver his best at work, whatever he's doing. I started to think about who I was as a whole person and not just who I was tied to the business. And I started to really work on like my own self and my own growth. And I think that that And so to be specific with what that looked like in my life, it was like, hey, 30 minutes every single day, you do something physical.

10:00No questions asked. Like your body is not something that you can put on hold. And every single morning, I started by reading something timelessly true, something that's bigger than the current problem of a startup. Like it's very easy when you face failure in a startup to think that that moment is the most important thing in the world. And by reading things that are old, by reading, I read poetry. I journal after I read poetry. Those type of things just helped me more consistently root myself in something bigger than kind of my startup and my startup being my everything. And so I think that that kind of recovery for me looked more less like trying to find the perfect job and more like recovering myself back to myself and not tying my own personal identity quite as much to my work.

10:48You need literal space from your work. Whether that's a retreat in the wilderness, reading, whatever, is why I go for a walk every day. And Adam has a view on failure and entrepreneurship, which is honestly as good as I've heard in a long time. I guess just to the listeners, I think what you're doing is remarkable. And I don't think you should undersell it. The hardest thing about a startup is that you're doing something amazing and it feels like failure the entire time. all the way until the end on the acquisition day, the most amazing events in the news, my family and friends are all sending me notes.

11:26I still felt like failure the whole time. It's like, because I was always like, but it could have been better. One decision this way, one decision that way. And so just to remind yourself, like you're doing something amazing and the energy that you're giving toward it is incredible and remarkable. And, and, um, and so just, just keep going.

11:49That was Adam Weber. Thanks for listening to this episode. I've been your host, Dan Murray-Serta. If you like this episode, please share it with a friend. See you next time.