“We should have been less afraid to have the tough conversation sooner."

Before Foxbox, Rob was CTO and Co-founder of Detective by Charlie, the Intelligence Platform for Sellers. Every day, thousands of sellers use Detective to prospect research to win the trust of any executive they call. But guess what? It wasn’t always that way! The platform began as just Charlie, a digital assistant. And the experience taught Rob a lot about accepting hard facts and having tough conversations. Let’s get into it.

FF: Please, Rob. Tell us about your burn!

Rob: So I moved from Denver to Chicago to partner with my co-founder Aaron to build Charlie. It was his vision. His idea was to create a virtual assistant that would brief you before all your meetings. It gave you a one-pager before the meeting to prepare you. It was a straightforward product and it resonated with everyone. We decided to do a private beta launch. And we were targeting a broad audience of anybody who had a lot of meetings. Aaron was able to secure some really good funding in the beginning, and then even better funding later on. We did a lot of customer development through that process. We spoke to customers, asked what they wanted, and we tried to understand their experience. We said, ‘okay, our strategy is to make this free until we’ve got the product more developed,’ and so that free period lasted like two years.

FF: I have a sense of where this might be going already. But please. Do tell.

Rob: Right. And so at one point we said, ‘OK, we've got to rip off the Band-Aid and get this out there.’ We believed in the product. And we hired this incredible PR guy to help us get into all the tech blogs. So we got coverage better than he imagined in TechCrunch, Mashable, VentureBeat, Business Insider, all the big ones, And the response was tremendous. Like 200,000 people signed up. It was a tidal wave. And we thought, ‘OK, we made it.’

FF: But you didn’t. Did you? Because you weren’t charging for the product yet?

Rob: Yes, it wasn’t quite that simple! We got a lot of natural churn (people who tried the product out and then didn’t come back), but we also had a cohort of users who used it every day. That’s one thing. But then we started charging, and we had a $20-a-month product, and a $5 a month product, just to see what might happen. We were looking at the results, and simply there were not nearly the amount of people paying that we needed to have. Maybe one percent of customers paid for it, and so we didn’t have anywhere near the volume that we would need to make this a business. And we looked at it and we were just like, “f__k, it isn’t going to work.’ It was very clear that ultimately it was more of a proverbial vitamin, not a painkiller. We had created something that was nice to have. It was like a friend you have, but you’re not going to date them. People just weren’t willing to pay for it. In hindsight I think we should have charged a small amount to test the business model from the beginning. And then LinkedIn shut off their API and that was a huge issue. Because they know there’s a lot of very valuable information in there.

FF: Yikes. I’m so sorry to hear that. What happened next?

Rob: At some point we brought the team together and we said, ‘guys, this is the hardest conversation, but this isn't working, this is the thing that we all came here to build and it's not working.’ And we were so afraid of that conversation because we thought that everyone would just leave and it would be so demoralizing. But they were actually said, “we know,” and they were on board to figure it out with us. And what started as the most scary conversation ended up to be motivating. We walked away just pumped up, like, ‘we can do this.’ And it's just a testament to my team. They're all so awesome.

FF: So you went through a year-long period of more customer development?

Rob: Yes the team, Curtis, Jack, and Dave, they came together and rallied. We had this loyal base of users, and we decided to target salespeople because they’re the ones who really feel the pain of the cold call. We talked not only to them as end users, but to their employers as well. And that’s another lesson we learned. Like, for a junior-level salesperson, they’re not going to pay for this. But their company is because it makes them more successful. And ultimately Charlie evolved into Detective, which saves salespeople thousands of hours by researching their prospects, and hugely improves cold call conversion by highlighting sellers’ activity with the customer’s relevant peers. We really wanted to go deep into what salespeople do, and allow them to get the information that they need to do their job. And through that, we created a profitable business. It’s still profitable to this day. And we landed some very big customers.

FF: Wow. And so this terrifying conversation turns out to have been the best conversation you could have had?

Rob: Yeah. And in hindsight, we should have had it sooner, because we were trying to figure things out and not tell our team until we had a solution. We probably went on for weeks until we finally told them. But they didn't need a solution, they just needed to be told. And also, they knew already.  

FF: Yeah, Rob, like, I can't help noticing, I was doing my own, er, detective work, and  looking at your LinkedIn before we talked. And there was another conversation you didn't have until relatively late, that was probably quite frightening for you, right? That it turns out has been really wonderful? (Rob came out when he was 30).

Rob: It certainly has saved my life and it’s true, I don't love difficult conversations. You're right! And it’s the same thing. I learned in hindsight either that people knew or people didn't care or, you know, already knew. And really, I should have had the conversation a lot sooner!

FF: I feel like what we're doing here is a combination of talking about tech and development and facing difficult emotional conversations and personal growth. And it turns out they’re a lot more interlinked than most people might realize, right?

Rob: It’s true. And you know the real parallel between those two experiences is that what allowed me to actually have the conversation in the first place was the internal acceptance. So I was struggling with my identity and I didn't truly accept who I was. Then when I did, that’s why I came out. And with Charlie, we didn’t accept that it was a failure. And then when we did accept it, then there was no turning back. We had the tough talk. It’s about that internal acceptance. You have to accept the hard facts and the reality.

FF: And more power to you, Rob. I’m so grateful you went there. And now you run this agency that’s grown to, like, how many people?

Rob: Let me check [checks on his computer]. Yes, we’re at 75 people today. We’ve grown 30 percent the last two months. It’s been...crazy.

FF: And could you have got here without having those difficult conversations?

Rob: No. Without coming out, I wouldn't have been able to achieve any of this. I've learned that I've got to live my authentic self in order to really lean into anything. Whenever you have these things that you're holding back from others, they’re on your mind, and they're detracting you from really being able to fully engage in something. The Charlie/Detective experience was the first thing I did, post-coming-out. And when I started Foxbox and leaned in, I was there, I was in a great state of mind, I was confident. And I still don’t relish the difficult conversations, honestly. But I certainly know it’s a good idea to have them sooner.

FF: Wow. I feel like I learned a lot from this conversation and I know our readers will be so pleased to learn from you. Thanks so much, Rob!

Rob: Thank you. It’s been a pleasure.

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