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Step inside real founder conversations: raw, unrehearsed, and honest. No playbook. No polish. Just ambitious entrepreneurs uncovering the answers that were there all along. Because every business hides something valuable trapped under the weight of success and chaos of growth.
The Hidden Value podcast is hosted by David Sherry. David works with early-stage founders to grow professionally and personally. He founded, sold, and advises Death to Stock – a media company and newsletter that serves brands like Unfold, Figma, and Spotify.
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All right, Chris, so happy to be here with you today.
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Looking forward to diving in a little bit more on Hidden Value.
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And I'd love to start with maybe a little context and kind of background of how you
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kind of got to where you are today.
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And feel free to share as much or as little as you'd like there.
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Yes, David, so excited for you to have me.
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I really, really appreciate your time.
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Let's see, so I am, I call myself a recovering journalist.
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I started my career as a financial news journalist.
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New York City through the kind of financial crisis.
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And I ended up on the West Coast coming out of the financial crisis.
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Tech always leads the way.
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They sent me out to the West Coast and covered tech.
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And this was during the rise of social media and a lot of the big names in Silicon Valley.
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And as I was reporting on them, I felt kind of two really big things in my life.
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One was that it felt boring to sit on the sidelines and kind of watch and report on it.
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And I really wanted to build and do things myself.
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And I think the second was that I would interview some of these really big names,
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you know,
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Mark Zuckerberg and Mark Pincus and Elon Musk before they were huge people.
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And I just remember thinking and I'm not trying to say this from a from a arrogant
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standpoint,
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but I remember thinking they're not that much smarter than me.
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Right.
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Like I could do this.
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I could go build things.
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I can I can have impact on the world instead of just kind of watching from the sidelines.
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And so that's what got me started into the tech world.
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And I joined through,
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I went to an innovation consultancy called IDEO and I learned kind of a methodology
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for innovation.
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And then I eventually transitioned to being fully in tech as a product leader.
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And I've done that for the last decade and it's been really wonderful getting to
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get my hands dirty and do things.
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But I'm at an inflection point in my life where I feel that itch again to want to
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do something more and something different.
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And a huge part of it has been wanting to kind of build my own practices and my own
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companies and wanting to
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really leave a different type of impact on the world.
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And so that's where I am at this stage.
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I've started a consulting business on the one hand where I'm working with Main
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Street operators and doing some fractional product work,
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fractional chief product work.
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And on the other side, I really like this idea of learning by doing.
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I am launching a Main Street business myself in my local region of Lake Tahoe,
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which is a night nanny service.
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which you would think this area has it, but it doesn't.
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What I'm really interested in doing related to this is understanding how we can
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apply and how I can apply all that I've learned to kind of high-end tech services
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and all this new AI technology.
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How can we apply that to really foundational services businesses that are
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fundamentally intimate and not,
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quote,
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scalable,
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as Silicon Valley teaches you?
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So that is the intersection of how I've arrived at where I am.
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Yeah, I love it.
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And it's such an interesting set of experiences.
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I think to be face to face with some of those leaders and kind of see behind the
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curtain,
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it must have been really,
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yeah,
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interesting for your own awareness.
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And then to feel maybe I want to be not as much in the sidelines.
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Maybe I want to do something myself.
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Maybe these people we look up to in a certain way,
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like,
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okay,
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yes,
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they're smart,
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but I can do something too.
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So it's really cool to be able to have
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almost those firsthand experiences where you got to see for yourself,
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how do I kind of receive that myself?
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And so you're taking all these skills,
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you're packaging them together,
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and you're turning that into a new offering.
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Let's talk about,
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you said sort of inflection point for my life,
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which I thought was interesting,
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not just my business.
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What's kind of the challenge you're starting to feel
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As you move into this new chapter, you've been through career changes before.
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What are you feeling is kind of coming up in this new change?
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Yeah,
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you know,
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David,
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I'm very curious if you've heard this from other people or if you yourself have
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experienced this.
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But I, you know, I mean, we could say I'm going through the classic midlife transition, right?
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I just have two children under the age of three.
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I just hit, quote unquote, midlife.
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And I think part of the way that I'm viewing this now,
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this next part of my life is,
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you know,
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I've had all these ambitions and I've accomplished so much that I'm really proud
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of.
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But what do I actually what is the life I actually want to live with my family?
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What is the legacy I want to leave?
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Right.
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And I'm not sure that.
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building technology for other people is the legacy I want to leave.
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I'm not sure that trying to continue to climb some kind of arbitrary corporate
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ladder is the ambition that I want to pursue.
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And so I think that that's when I talk about the inflection point,
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that's a little bit of where it's come from,
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which I'm sure is where a lot of entrepreneurs come to
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to be.
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And I actually read an interesting statistic that most successful female
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entrepreneurs start entrepreneurship in their 40s,
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which I find fascinating.
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But it also makes a lot of sense to me because I think that you've had all these
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experiences that have leveled up into like a clear understanding of what you can
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bring to the table.
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And sometimes we take a little bit longer,
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I think,
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women sometimes in bringing that into a clear confidence to bring forth.
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And so that's when I talk about an inflection point, that's kind of what I'm referring to.
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Yeah.
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And you said like,
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I'm not sure,
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you know,
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if the technology in that way or the legacy in that way,
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is it clear what the legacy is and what the way of kind of building is for you in
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this phase?
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Like how clear is the vision that you have for this lifestyle or this type of
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business you want to build?
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One thing I think I learned really early on in life,
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like,
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you know,
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I was a reporter for Bloomberg and NPR and I had,
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you know,
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audiences that were global,
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for lack of a better term.
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And I loved that impact at scale.
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And that was really important to me when I moved into more of the corporate world
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that I wanted impact at scale.
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And I worked for global companies like Uber, for instance.
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And I always have loved that what I build has impact at scale.
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But one of the things I also learned in my journey when I was working at IDEO,
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when we were at IDEO as an innovation consultancy and I was with the nonprofit arm
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and a lot of the work that we did was in the developing world,
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in India,
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in Ghana,
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Kenya.
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And I remember that consulting approach that I built and we did a lot of things,
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but I never got to see it come to fruition.
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And I didn't feel like it had, quote, impact.
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but that the impact that I could have was relational with the people that I was
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working with on the ground and what they were learning about how to innovate in
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their own processes in their own communities.
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And I really love that.
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And that stayed with me.
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And even as I've grown,
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you know,
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VP of product at a startup,
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a tech company,
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my favorite part of the role is really the impact I have relationally on the
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individuals beneath me.
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And so I think one thing that I've learned as I move into this next stage is
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Scale is less important to me, interestingly enough.
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What I'm realizing is the impact,
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that relational impact and the ability to really make a difference in my community
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and or at a smaller level is starting to matter more,
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surprisingly.
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So I think that's something maybe that's been coming up.
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Totally makes sense.
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And I've actually,
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I actually feel like I've gone through a similar shift of mindset as well as this
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more relational impact.
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What does relational impact look like to you?
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I think, you know, there's like the there's the professional side.
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Right.
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And then there's kind of more of the personal side.
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What I'm really enjoying in some of the consulting work that I'm doing is when you
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work with small businesses and I'm really focused on kind of main street services
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businesses,
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you get to iterate really quickly and you get to see if it works or it doesn't
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work.
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And that foundationally impacts the founder,
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the leader of that organization,
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because,
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you know,
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you're not working with this massive team.
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It's not really abstracted or removed away.
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The impact is, let's make that concrete.
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So the impact is, you know, do you want to kind of make that concrete?
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Immediate, maybe?
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Immediate impact.
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You like to feel the immediate impact of working with someone hands-on.
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And that helps them because they can, what do you think?
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They can move faster.
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They feel the value of that.
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How do you think it helps them?
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Yeah, I think I like that it helps them feel like they are self-fulfilling in some ways, right?
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That they're growing their businesses and that feels really good to them.
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They're able to reach their capabilities, their best capabilities.
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I like being able to help people with that.
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Yeah.
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And that's a clear service perspective,
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right,
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that I think you've picked up through these different experiences being in these
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different rooms.
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And the value now is sort of on the service of how are they growing?
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How are they expanding?
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And how you measure that sounds like it's almost sort of speed to impact.
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Oh, that's interesting.
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I hadn't thought of it in those terms.
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Yeah.
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Yeah.
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And so how do I provide,
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you know,
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maybe part of what you're exploring and what you do next is how do you,
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how do you get that feeling more?
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You know,
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cause I think part of what's driving this,
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what I'm hearing as well is that other people might come on here and talk about
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financial or,
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you know,
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being on stages or whatever.
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And so you're kind of identifying this feeling that you want to be having maybe
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with more people in your community.
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And it sounds like it's local as well.
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So, so help me understand that a little bit.
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Um,
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Yeah.
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How's it been connecting with people in your community to have that type of
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relationship or that type of partnership?
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It's scary because you can't hide behind a product experience or numbers or scale.
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You know,
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when I was a TV journalist,
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I could talk to really important,
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quote unquote,
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important people.
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And you can kind of hide behind the scale and the, you know,
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the one-off interviews at large tech companies.
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So you're hiding behind the scale.
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Sorry, I'm just trying to make sure I understand.
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Yeah, I think you can hide behind the scale.
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I think that you can obfuscate your impact and blame scale to some extent, potentially.
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And if it's not blamed on scale,
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like it's blamed on you for the lack of impact or something,
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or what's kind of underneath that,
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do you think?
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Yeah, I don't know.
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Maybe there's more responsibility when you're in business for yourself and you're
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an entrepreneur.
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At the end of the day, you either deliver a result or not.
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And there's not really much to hide behind.
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You can't blame anything, anyone, any technology.
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Yeah, yeah.
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So,
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you know,
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sometimes what can happen and kind of what I'm hearing is that there's this sort of
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joy of impact and speed to impact in this relationship,
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relational impact that you can build.
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And maybe on occasion that can be slowed down by fear.
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I mean, this is just we all experience this right in different ways that
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this fear kind of shows up.
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The flavor of the fear for you happens to be maybe a little bit around like,
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without this kind of scale,
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you know,
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thing,
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now the responsibility is on me.
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And so do I want to put myself into that responsibility?
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You know, that can be the
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the inner dialogue that can kind of maybe pushes and pulls a little bit.
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Maybe how does this resonate for you?
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Do you feel, if I ask like, do you feel clear and confident that you want the responsibility?
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Do I want this responsibility?
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Is that question clear to you what the answer is?
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No, definitely not.
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I mean, I believe in radical responsibility, right?
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I teach that to my team.
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So when you're managing a team of product managers or managing a team,
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it's very different than like you're the person now responsible for moving the
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metric.
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It's almost moving back in my career in some ways to when I'm like an IC.
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But I like that, I guess, is what I'm saying.
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That's so interesting.
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But it's scary.
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Yeah.
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Yeah.
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Yeah.
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Well, and it sounds like you've done that.
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You've, you've liked that taking on that responsibility.
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You teach it to other people.
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And so I'm,
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I'm curious now about how,
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you know,
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is there any difference there actually,
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or,
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or how is that same way of viewing things just applied here?
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You know,
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if you did it in that situation,
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which many other people would feel a lot of weight and responsibility and like
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is there any difference actually?
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Yeah, that's a great question.
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I mean,
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yeah,
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I guess the meta question that you're asking,
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David,
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is,
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you know,
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there's so many layers here,
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right?
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You can move through levels, layers of responsibility, abstraction layers in a career.
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I'm choosing in some way to go back and engage in ways that I have in the past.
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Part of what I feel you're pulling on is like, is that going to
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meet your needs or desires at this time in your life as an entrepreneur, as a professional.
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Is that kind of where that's going?
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I actually think it sounds very genuine what you're wanting and this kind of impact
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and this responsibility.
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I hear a little hesitancy maybe to take on the responsibility because it's like,
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it's a little scary.
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It's a little unclear.
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Do I want this?
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What I was really trying to surface was there are these other areas that you felt
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very comfortable taking on that responsibility that you enjoyed it.
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And I'm sort of wondering,
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what's interesting to me is at scale,
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I actually think that sounds like a lot more responsibility.
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If it's with the whole team managing a product, a technology is going to reach out.
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Like that sounds like so much responsibility.
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I'm scared to do that.
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And maybe to connect with somebody relationally.
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you know, in that direct way.
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There's collaboration and maybe there's some responsibility,
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but it actually doesn't feel as heavy as the others.
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So that's what's interesting to me.
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No, I appreciate you pointing out that tension.
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You know,
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one of the things that I've always loved in my career that I've always prided
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myself as a type of leader I am
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And what I've done is by being really close to like actual user needs.
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Right.
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And by representing that all the time.
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And that's really hard sometimes in these corporate environments or in these like
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large environments is to constantly bring people back to.
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Yeah.
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But what are we like?
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What is the user actually need versus what the business needs or how you find that
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intersection of both of them?
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And how do you keep that truth and that empathy and.
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And I think what I've maybe this is just what I've realized.
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And again, midlife is a lot of companies won't.
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They just will let go of that in some ways.
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So what if the responsibility is to the user not
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of the weight of the responsibility with the business owner, right?
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What if your role as you enter these companies and these collaborations with these
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mainstream businesses is to say,
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Hey,
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I'm here to represent the user.
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That's the responsibility you're taking on.
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You're not taking on,
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which I can understand the weight of their business,
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their problems,
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all of that,
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which it's easy to take that on because it is leaking out everywhere just because
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that's how it is to be a business owner.
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Like, how does that maybe feel?
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I,
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That's an excellent reframing.
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I hadn't even thought about it in that way, which is, yeah, and that's the scary part, right?
(00:14:32):
When you're charging this amount of money that suddenly is for your direct result,
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it's not a paycheck.
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It's going to depend on the impact that you give them.
(00:14:41):
You really want those results to show.
(00:14:44):
But what you're saying is,
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how can you just represent the user need again and trust the process that I've
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already learned through all my other jobs and careers that if I represent the user
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need,
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that we will
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very likely correlate to success for the business as well.
(00:15:01):
I think totally that.
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And I'm sort of saying that that's the responsibility that you want.
(00:15:07):
I don't know if you actually want this other responsibility.
(00:15:09):
You might choose that you want it, which is taking on the business's pressures and all that.
(00:15:14):
I take on that responsibility.
(00:15:15):
That's kind of what I do, but it's always, it's different, right?
(00:15:18):
And so I'm saying,
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I think maybe the clarity is the responsibility that I want to take in this
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relationship,
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in this offer,
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is that of representing the customer,
(00:15:29):
representing the user.
(00:15:30):
I like that.
(00:15:31):
How does that sort of feel to you?
(00:15:34):
Yeah, I mean, it definitely sits well.
(00:15:36):
I think that it's just a reframing, I think, of how I've been thinking about it.
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It does take the pressure off to some extent.
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Is something else still there?
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Because one of the things I think we can get to is how we might create some more
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progress in a particular area you're wanting.
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Is there any other sort of stressor around this or lack of clarity here?
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Yeah.
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No,
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and I think what's like dancing around all of this is that when you go into
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business for yourself,
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at the end of the day,
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what you're doing more than you've ever done in your life is sales.
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And sales feels really uncomfortable, right?
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That's not something that I've been trained in or do very well or something that
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I've done in my life,
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really.
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And so part of what you and I are dancing around right now is what am I actually selling?
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Am I selling the support to a user, to a business owner, right?
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Or am I selling the partnerships
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in representing needs of the users.
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Right.
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And I think that framing does matter in some ways.
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And maybe I would be feel more comfortable and then I'm not trying to sell myself.
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I'm trying to sell like you need a partner and thinking through how to serve your user.
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totally i think that can really land and i think you can connect it to things that
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are relevant hey i know you're trying to work on sales or product design or
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whatever my role is that i'll think through the process of kind of owning that that
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customer perspective to impact the product or to impact the sales or whatever it
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might be and i think you're maybe your sort of special sauce is i really care about
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speed to impact
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So my goal in this project we're working on together or whatever you outline is
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getting you there quickly.
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Like we should know if this is working.
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So maybe pairing those two things together as part of your sales offer.
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I really appreciate you saying that,
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David,
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because I actually had two clients in the last month.
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They said offhanded,
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like you've done more for us in 30 days or whatever than we've like seen ever in
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the history of our company.
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And I didn't even think about that as like a value prop is like I'm just like fast
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and I hustle and that's kind of how I show up.
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That's huge.
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I think both of those skills and ways of working are massively helpful.
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Here's kind of what I'd recommend we kind of talk about now is,
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you know,
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how do you kind of take some of this and maybe experiment a little more to see for
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yourself,
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hey,
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does this sort of help me move forward?
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The first thing I'd recommend,
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and I want to maybe brainstorm with you on the other actions or ideas,
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is those testimonials.
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Like,
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capture those or own those or start to just see what is it like can I own that like
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okay these these people said you've done more in 30 days than a bunch of people can
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I can you make that a part of your brand just try it on so I would capture that and
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make them more forward-facing if you haven't and I'm going to tie it back to what
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you brought up which is to the sales conversation or to how you represent your
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offer maybe bring that in that would be one that how does that sound and can we
(00:18:36):
talk about some other ideas
(00:18:38):
Yeah, no, I love that.
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I think one thing I get scared of,
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David,
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is that we all operate at different levels and backgrounds.
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And when I hear speed, I feel like Silicon Valley speed scares me.
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It's exhausting to me.
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But I think what's interesting is how do I find what's the right speed for me?
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And I think you're right.
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I think it by default is faster than other industries and sectors.
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I think you like it, too.
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I actually think you're wanting that.
(00:19:05):
Like you told me earlier that the speed to impact is kind of part of the like juicy
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relational impact that you feel as well as helping them grow.
(00:19:14):
So I actually think that that's part of maybe what you want to provide.
(00:19:18):
And you can you can let them language it.
(00:19:21):
Yeah, that's a helpful that's a helpful mirror.
(00:19:24):
I really appreciate you saying that, David.
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Yeah, because I think you're right.
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So to me, I hear two pieces.
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It's gathering some testimonials about this speed to impact,
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speaking to that,
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kind of owning it.
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If it starts to feel comfortable that, hey, this is what I do.
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This is what people say.
(00:19:39):
Everyone says that this is faster than most.
(00:19:41):
And my role is to represent and take responsibility for the user, the customer experience.
(00:19:49):
And I think it's tying that to something in the business, right?
(00:19:52):
Their product design, or you'll figure out that part of it.
(00:19:57):
And here's why that will help progress things for you, you know, explaining that.
(00:20:01):
Yeah.
(00:20:03):
No, this is really helpful synthesis.
(00:20:05):
Yeah.
(00:20:07):
What else is right in front of you just to kind of wrap on that might be now
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testable,
(00:20:13):
actionable?
(00:20:14):
Is there anything else that just through this now you're thinking like,
(00:20:16):
huh,
(00:20:16):
I could maybe go do X now as a test or as a experiment?
(00:20:21):
To be entirely honest, David, it's scary to me to ask somebody for a
(00:20:27):
a review or a reference or to get a testimonial.
(00:20:30):
And I think part of that just comes from,
(00:20:32):
I love feedback,
(00:20:33):
but I actually prefer critical feedback.
(00:20:35):
I find it really hard to accept or sit with positive feedback.
(00:20:40):
And I think that's a new phase for me that I have to embrace if I'm in business for myself.
(00:20:46):
It's going to start feeling really good to start accepting some positive feedback.
(00:20:51):
I've really enjoyed this conversation.
(00:20:53):
And so I want to tell you that.
(00:20:54):
And I've enjoyed our conversation prior to this as well.
(00:20:58):
So I'm just going to give you some of that feedback because it's going to make you
(00:21:00):
a little uncomfortable maybe.
(00:21:03):
And I think that's where I would action on next.
(00:21:08):
And you can include both.
(00:21:09):
Hey, it was great working with you.
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I would love some positive feedback of what you noticed stood out about working with me.
(00:21:15):
I'd also love some critical feedback because I'm always trying to improve or
(00:21:18):
whatever you might say.
(00:21:19):
So that's what I would do next is a small experiment.
(00:21:23):
You know, how does that, does that sound achievable?
(00:21:25):
Yeah, absolutely.
(00:21:27):
Okay.
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That's the least I could do, right?
(00:21:31):
And then your pitch is supported,
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your offer,
(00:21:34):
your sales are supported by what other people are saying.
(00:21:37):
You know, you don't have to even write some of the copy or whatever.
(00:21:39):
It's other people have recommended or said this about me.
(00:21:43):
That's kind of nice too, you know?
(00:21:44):
Yeah, it's so different.
(00:21:49):
It's so different when you're asking for feedback on a product,
(00:21:52):
which is inherently abstracted away from you than when you are the product in your
(00:21:56):
business.
(00:21:59):
Yeah.
(00:22:00):
The big growth potential here,
(00:22:02):
and I'm seeing it a little more now,
(00:22:04):
is this abstract versus personal responsibility dynamic scale versus,
(00:22:11):
right?
(00:22:11):
So that's really the bigger opportunity I think is possible for growth is starting
(00:22:18):
to see how that's showing up in these different areas,
(00:22:20):
because I'm hearing it a little again now.
(00:22:22):
And as you find that
(00:22:26):
Maybe that isn't doesn't work the exact way you think where scale means less scary
(00:22:31):
and small means more scary.
(00:22:33):
As you explore that,
(00:22:33):
I think that's part of what can really unlock this other type of work and really
(00:22:39):
just the next chapter for you.
(00:22:40):
You've done so many amazing things already.
(00:22:42):
But I think that's the personal growth piece that really will expand things the most.
(00:22:46):
I really appreciate that, David.
(00:22:47):
This is really helpful.
(00:22:48):
Thank you.
(00:22:50):
Thank you.