In this interview, Bobby recounts a painful career episode that began with a headhunt to a "dream" product role that turned toxic after six weeks, leading to a six‑week tenure that left him feeling traumatized and resulted in 18 months of unemployment and low‑confidence consulting work. He describes the spiral of self‑blame, feelings of worthlessness, and the market freeze that compounded his distress. Bobby then explains why he chose to invest in Lynne Levy’s coaching program despite financial constraints. He highlights the program’s Montessori‑style group work, which provided peer accountability, emotional regulation tools, and a space to rediscover his strengths—particularly his humor and gregariousness. Through the coaching, he clarified his unique value proposition, crafting a personal brand narrative that frames him as a scientist by education, an explorer by nature, and an accidental entrepreneur. This reframing, combined with community support, helped him re‑enter the job market, negotiate a director‑level product role, and secure a position as Director of Product at a startup. The testimonial underscores the importance of personal branding, peer community, and emotional resilience in career recovery.
Chapters
Um, I made the case that this should be a, uh, a director-level role and, um, they agreed. So I'm a director of product at a startup.
Boom.
Yep. Yep.
Total rock star. Where were you before we decided to work together?
I had been unemployed for 18 months. I've been doing like a little bit of consulting work, but I, I, uh, yeah, I had, I had, I was at a company. Um, I had a pretty good job, uh, product manager leading a product team. Um, and I left to, I was headhunted away to what I thought was going to be my dream job at the dream company. Um, doing the kind of things that I really like to do, which is like that, I don't know, building product teams was sort of what I was lured away with. And then when I got there, it was not that. And it was like everything that, that we then learned how to address in your program, actually. And, you know, maybe things would be different, but it was also probably for the best that I got out of that crazy situation. And And yeah, it ended rather abruptly. I went to sign into my computer one day and couldn't, like it was that toxic. I was there for 6 weeks. It was traumatizing. I consider myself a fairly resilient person. And, and I don't know, as product people, we're used to a little bit of uncertainty, you're used to like a little bit of chaos and navigating a lot of these things, and maybe it, you know, comes with some practice, but a little bit comes naturally. And so then to feel like that is just ripped out of you, that's the traumatizing part. So I can imagine that a lot of you here today maybe feel similarly to that. And I was, yeah, I was devastated. I blamed myself. I did all the wrong things. That is to say, exiting that experience, I spiraled. I was like, there's, you know, you're, you're, what the hell do you know? You, you don't know how product works. You don't know how to whatever, do this job. You can't manage up. Well, it's, you know, it's hard to like have your wings. I guess sometimes I described it as having your wings clipped, but it felt like having my wings ripped off. You know, and I feel like as product people, part of our mindset is that there's always another lever to pull, a knob to turn. I am very much like pulling strings, you know, to try to find a better way forward. And then when, when that's just, you're just, the door is slammed in your face and you think that it's, that this was going to be the thing. That's really hard. So yeah, so I beat myself up and spiraled and spent about 18 months unemployed, phoning it in, frankly, right? And then, and up to that point, and I think that a lot of you probably felt this way too, like recruiters were knocking down my door to, to get me out of the job that I was in and into another roll. And then it was like the market just evaporated, which was also crazy. And so then for those things to like line up, then you really feel like you're worthless, right? But you do get to a point where, uh, something's gotta change or you become a self-fulfilling prophecy in a lot of ways.
And, um, and that was kind of when we found each other So what made you decide, in spite of being financially constrained, being out of work, to invest in yourself? What made you decide to take the risk?
In our initial call, you identified a couple of things that, like, I don't know, just sort of reinvigorated me in a lot of ways of just like, oh, I do have value. You immediately recognized that, like, Because I can be, I think, gregarious, you know, and a fun person, generally speaking. I mean, one of my strengths— you guys might do some of this strengths exercise stuff— but is in humor. And one of the things that I really learned through the program was that, like, the things that you take for granted in yourself are the things that make you unique, special, and powerful. Humor was a thing that I had I had sort of taken for granted or thought was like a negative. But it turns out if you apply it correctly and apply it strategically or with a little bit of wisdom, it can be a really powerful and inspiring tool. So and then you identified like this sort of unique— what my unique value proposition could be or like a version of it. And while I didn't land in that, intersection, it still helped me think outside the box and think about the strengths that I do have that make me unique and valuable and bring impact where I can. So, and, and I, the, the thing that made the big difference for me was the group work. I, I kind of describe it as like a Montessori coaching program. Like, you're not going to learn product fundamentals here. If you want to work on those things, you absolutely should, but you're going to learn like how to, well, how to keep yourself from getting triggered and then how to manage it when you are and how to manage it when other people are. And what's so encouraging about the sort of group work is that you are in this group of people who are at all different places in their careers, and that's sort of the Montessori part of it, right? And also at different places in the program. And so you just have this sort of And then you're surrounded by people who are like in similar places to you and also motivated to, to move their careers to the next level. Even when you're feeling unmotivated, the, the only thing that you actually have to do is show up. Because also when you're surrounded by 20, 30 other people who have showed up and then remember that like, man, they probably felt the exact same way as I did showing up to this meeting. That is like the barrier breaker that you need to then show up and participate and, and be active in the conversation.
And tell folks, what is your brand? How would you describe your brand, your unique value proposition that we came up with?
My tell me about yourself is I sort of describe myself as a scientist by education, an explorer by nature and an entrepreneur by accident. And, and I consider— I say by accident because I never set out to start a company. I set out to solve a problem. And then if we can turn it into a business at the same time, then all the better. And that is sort of what has guided me through my career. That's sort of been like this central thread. And I have a very strange career, but it's that like connecting thread of the way that you think about problems. That's what your unique value proposition is. That's what makes your— that's what makes you valuable as a product person, you know, to a company. And that's the story that you have to tell.
So if you— so you're talking to a— to you, all these folks 18 months ago, what would you tell them?
You're not alone. And, and that means so many things. You know, like, it's just like knowing that, yeah, like, people care. So, you know, you're not alone in that way too, right? Like, you have people around you often, but you can still feel alone. And part of that is just like, you do it to yourself. And so then just Just knowing that like you're not alone and that you're not the only person who's trying to navigate this right now, but that also you don't have to do it alone.
And it's an amazing community. The alumni, you're going to— it's 600+ amazing rock stars in product who care. This is a community of senior-level product folks who— I don't code. We don't talk about how to prioritize requirements. That's not what this is. This is about landing, leading, and thriving. So thank you, Bobbi. I so appreciate—
