Hidden Value with David Sherry

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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?

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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.

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You really want those results to show.

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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.

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I think totally that.

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And I'm sort of saying that that's the responsibility that you want.

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I don't know if you actually want this other responsibility.

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You might choose that you want it, which is taking on the business's pressures and all that.

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I take on that responsibility.

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That's kind of what I do, but it's always, it's different, right?

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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,

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representing the user.

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I like that.

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How does that sort of feel to you?

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Yeah, I mean, it definitely sits well.

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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.

(00:16:32):
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.

(00:16:43):
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

(00:17:08):
speed to impact

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So my goal in this project we're working on together or whatever you outline is

(00:17:14):
getting you there quickly.

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Like we should know if this is working.

(00:17:17):
So maybe pairing those two things together as part of your sales offer.

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I really appreciate you saying that,

(00:17:23):
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

(00:17:32):
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.

(00:17:39):
That's huge.

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I think both of those skills and ways of working are massively helpful.

(00:17:48):
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,

(00:17:58):
hey,

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does this sort of help me move forward?

(00:18:01):
The first thing I'd recommend,

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and I want to maybe brainstorm with you on the other actions or ideas,

(00:18:06):
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

(00:18:13):
okay these these people said you've done more in 30 days than a bunch of people can

(00:18:18):
I can you make that a part of your brand just try it on so I would capture that and

(00:18:23):
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

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talk about some other ideas

(00:18:38):
Yeah, no, I love that.

(00:18:39):
I think one thing I get scared of,

(00:18:40):
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?

(00:18:56):
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.

(00:19:38):
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,

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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.

(00:21:29):
That's the least I could do, right?

(00:21:31):
And then your pitch is supported,

(00:21:33):
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.