Hidden Value with David Sherry

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All right, welcome back to Hidden Value.

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I'm here today with Andrew Fink.

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Andrew, thank you so much for being here.

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I have some notes from some of the questions you submitted,

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so I'm excited to dive in,

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but welcome to the show.

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Yeah, thanks, David.

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I'm really excited to be here.

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You know,

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I think a great place to start is just a little bit of kind of how you kind of find

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yourself here.

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So do you want to give me just a quick overview of what the last kind of year up

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until now has looked like for you?

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Yeah, totally.

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So the last year has been, I'd say, a year of experimentation for me.

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I was coming off quitting a corporate job of working in management consulting for

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four or five years out of college.

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And I had reached this point where I

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I was enjoying it and I was learning new things,

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but I had reached that level of manager where I was like,

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I saw the people 20 years ahead of me and I was like,

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that's not the path that I wanted to go down.

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And so I was still early enough in my career and had some entrepreneurial itch of

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like,

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I want to take a risk or like now's the time to take a risk and try something

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different.

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But I didn't know exactly what that was.

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So I had taken some time off and traveled and just tried to get some space to

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figure out what it is I wanted to do next.

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So that was the end of last year, 2024.

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And then over the past year, it's been trying different things.

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And what I found is I really enjoy writing.

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And so I started my own newsletter, just sharing my experiences and my journey with

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through quitting my corporate job and my travels.

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And then it just kind of snowballed from there.

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I was writing for myself and then I learned about ghostwriting and started writing

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for other folks.

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And it's led to numerous different types of projects to where I am now,

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where I'm working with founders,

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helping them write newsletters,

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LinkedIn posts,

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as well as I'm getting into some more longer form like book writing as well.

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I know we're going to talk some maybe about where you're at.

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Something already struck me that I'm curious to ask about,

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which is what is your relationship today with risk?

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So you kind of, that caught my ear a little bit, right?

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That I wanted to kind of maybe take a risk, saw this path.

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I didn't want to take it.

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You've taken some risks now to step into this new space.

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How, yeah, what do you think your relationship with risk is today?

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I'd say I'm a pretty risky person or I'm on the spectrum of like,

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I'm willing to bet on myself and take those risks.

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But I would also say that

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they've been, they've been definitely been calculated and like, I am like deliberate.

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I'm like, one of my values is like deliberate decision-making.

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And so I'm willing to like take those risks,

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but I do feel like I,

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I play out the scenarios and I do the what ifs and I've gone down the,

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you know,

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Tim Ferriss,

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like what's the worst possible case scenario to get okay with me taking the risks.

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And then I'm, then I'll go and

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So that's kind of maybe the style or position you're in now in terms of thinking

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about the future.

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What risk or what potential paths are you considering right now?

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So you've shifted, you left the corporate process

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A gig because you saw, hey, I don't want to, which is really smart.

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Hey, I see where I'm going to be in 20 years.

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I don't want to end there.

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So, you know, good on you for making that transition.

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You found something you enjoy writing.

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And it sounds like you're using the skill and an area of enjoyment in service of other people.

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So what's sort of that next stretch then?

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you're thinking about?

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And I'm also curious to maybe keep risk a little bit here in this discussion.

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And how are you thinking about risk as far as moving forward?

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So where I'm at now is I have like this solopreneur business where I do everything.

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I sell, I deliver on the work and all of that.

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And like, I'm, you know, making a good

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living and I enjoy it and things are good.

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Especially compared to where I was in the corporate world where I didn't have the

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freedom that I have and I didn't have the impact and the work that I'm able to have

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now.

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But this

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you know,

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the potential next step or the thing that's pulling me is like,

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do I want to grow this business beyond just a one-man shop?

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And what does that look like?

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How does that change things?

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And in terms of risk, have you been playing out that scenario?

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Because you just were saying, I play out these scenarios, I take this calculated risk.

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Where are you in that process as it relates to scaling up or building a bigger business?

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It's been harder for me to play out.

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I feel like I hear all of these stories of other folks who have grown and scaled businesses.

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And a lot of them are my clients.

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And so I'm in it and I see it and it's like,

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it's a grind for two,

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three,

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four or five years or more.

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They're sacrificing all these other parts of their life for their business early in

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their career.

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And I...

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have been able to build something where i can still you know i just got back from a

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fishing trip where i was off for three days and like i am training for a marathon

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and like i have all these other aspects of my life that are important to me and i

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don't want to sacrifice those to like build this business and i'm trying to like i

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guess that is also in factoring into my decision making and it's just and i'm like

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struggling with

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Can I do it all?

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Can I still continue to have these other aspects of my life and grow a big business?

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Or do I have to sacrifice it?

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And am I willing to make these other sacrifices?

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Or how much am I willing to sacrifice?

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I'm hearing that you are playing out some of that scenario through this lens of

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what these founders are sharing that,

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hey,

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you're going to have to sacrifice to do this.

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So maybe that's part of how you're imagining it could grow.

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And I'm thinking how similar are those founders that you're working with?

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How close to the path you're thinking about are they on?

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And what's interesting too is you played out your coworkers kind of moving forward.

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your managers,

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and that was pretty aligned,

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because it was like,

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oh,

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that's actually the path I'm moving into,

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right,

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like,

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that was a very direct path,

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yeah,

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I guess what comes to mind is I ask you how similar their path is to yours,

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they are as individuals even to you.

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Yeah,

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I mean,

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as you were saying that,

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it was like,

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because the corporate path is so cookie cutter,

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it's like,

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I could see what that looked like if I just kept getting the next promotion,

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the next promotion,

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and like,

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entrepreneurship there's like a million different ways that you can do it and so

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yeah so like what does that mean for your growth keep going with that so what does

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that mean keep going what does that mean yeah just there's like just more unknowns

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or more like it's harder for me to visualize exactly what that looks like for me

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and keep going so what does that mean i think it's just um

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I've been a little bit more hesitant or scared to make the jump like I did last

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time because it wasn't so as clear cut.

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Help me understand last time,

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was that at the job or was that you tried to maybe move forward in a certain way?

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Yeah, at the job, like when I left the consulting gig.

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Mm-hmm.

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Yeah,

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what I'm curious about,

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and I think a space,

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what I kind of heard in that or what I was interested in that was,

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oh,

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there's less structure,

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there's less rules.

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What's hard about that is,

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hey,

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I don't have any models or I have less models or I'm not really sure.

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That's kind of the difficult piece of it.

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The opportunity piece of it

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is, wait a second, there's actually more leeway here.

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There's not this set path that once I go down, it has to end in a certain place.

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It may be a bit more learn as I go, develop as I go, change as I go.

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And I think that lock-in risk,

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if I can call it that,

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of,

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well,

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I'm just on this path for the next 20 years,

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Maybe that's the flip side of not knowing is actually there's a lot more flexibility.

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That's kind of what I heard.

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Do you, how do you sort of hear what I'm bringing up?

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Yeah, I was actually like, I've been talking through this with other people as well.

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And even this morning, a couple of guys

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reflected back to me like when I had left my corporate job,

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I had always had this thing in the back of my head is like I could always go back

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there if I needed to because I left on good terms and it's like that consulting job

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is always gonna be there.

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I didn't really see this until this morning,

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but I could go back to this if I needed to and leaning towards growing an agency

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I could always come back to this if it doesn't feel right or whatever it might be.

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And so that's what that brought up for me when you were saying that.

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Yeah,

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and maybe that's what helps you feel comfortable with the calculated risk is

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knowing that you can shift back as you need to.

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I also think there's maybe a bit of an assumption here that

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you know, the sacrifice or what growth means is that I'm going to have to sacrifice.

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And it does sound like there's some desire of some type of gain that you can also

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get from taking this risk or making this leap.

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So let's talk about that because,

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you know,

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I know you don't want to maybe have this business take over your life and there's

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also something drawing you towards this.

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So what is appealing about this growth to you?

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What's pulling you into it?

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There's two things.

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One is just I am like a growth minded person.

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And so the taking on the next challenge and doing something hard and proving to

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myself that I can build this company.

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And then there's also just like the financial independence process.

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like having a fallback financially if I'm able to build a company,

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whereas on the solopreneur journey,

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it's not the same where I can like step out and have things running in that

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situation.

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And so those are the things that are drawing me towards it.

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I want to be challenged because I'm growth-minded.

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And I want to create some more upside or more financial growth for myself.

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And so those are two pieces that you might be wanting to find those regardless.

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Maybe one pathway is growing this agency.

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But what I will say,

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I tend to kind of see and notice is if you feel like that's true for you,

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that these questions are coming up,

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that these desires are coming up,

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it's kind of like a need,

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you know,

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we kind of all have these different needs and that's,

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that's perfectly okay.

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And those needs are maybe going to remain unless we find a way to meet those needs.

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And I think there's plenty of ways to do that.

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There's different ways to grow.

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You mentioned running a marathon, you know, or training, right?

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Like that's a growth mindset that you're engaging with to meet that need.

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And so I think for you,

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it's sort of like,

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no matter what,

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I see these things as kind of how we get energized and

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to move forward, right?

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Because for entrepreneurs,

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what happens is your excitement,

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your thrill,

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I call it,

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it's kind of what draws you into that next thing,

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right?

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You start to get this thing working,

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the writing,

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and it's like,

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it's exciting,

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and you're building,

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you're building.

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And then this plateau happens where if that learning and that growth isn't there,

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and also the financial piece,

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which can be a signal about growth for yourself,

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or also be something you're wanting to become in the future,

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if you don't have those things,

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you know,

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you're going to start to find,

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I want some method to have that in my life or in my business,

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right?

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So those questions,

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I think you can kind of figure out,

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do I want to meet those needs through the business?

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Or are there other pathways maybe that meet those needs as well?

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But I think the upside is they keep you energized.

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They move you forward.

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They're exciting.

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And so how much are those needs being met for you right now versus how much are you

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feeling like you're really wanting them?

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I think that's an interesting thing to explore.

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That's a good point because I do get the growth stuff in these other aspects of my

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life through the travel or through training for races or in my relationships.

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Do I need it everywhere?

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I don't know.

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I haven't really thought of it that way.

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I have noticed myself think in terms of black and white a lot as opposed to like

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The dimmers are just like it doesn't have to be all the way one way or the other.

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And so that's just like a natural thing that I do all the time.

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Yeah, look for a third option.

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I mean, really, there's many options.

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So I think there's many ways to get these needs met.

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There's many ways to grow your financial sort of opportunity.

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You could do a solo practice and co-found an agency and they could be separate, right?

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What I would recommend is find those things that are energizing for yourself

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because they're a need or desire.

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Build some pathways for you to actually move towards that more.

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your natural energy will drive you forward towards that.

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So if it's about the financial abundance piece for yourself in the future, some outlet for that.

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I think if you've got the excitement for it and desire, you want to have some outlet there.

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When you say finding this energy, can you elaborate on that or how do you go about that?

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I would look at where am I actually being pulled right now?

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You know,

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there's kind of this push and this force and we all experience this in different

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ways in our business,

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right?

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There's the things we're trying to kind of like force to come together.

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And those kind of feel like these like block doors where we keep like pushing and

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pushing and yet the resistance kind of pushes back.

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And then there's these other areas where we actually just have this natural excitement.

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And then as we step forward, hey, things are starting to kind of work.

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Things are starting to kind of unlock.

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Like I actually feel like things are building around this kind of naturally.

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And that could be with a partner,

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for example,

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like a co-founder or a collaborator for this business.

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Or maybe there's something around money or finances you're just actually feeling

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really drawn to.

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The reason this is important is because you don't have to motivate yourself every day

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to get the energy to do it.

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I don't need to keep having all this coffee and like,

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you know,

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what I see is all these productivity systems and stuff,

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a lot of times it's like people forcing themselves to try to do something they

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don't actually have the energy for.

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So you kind of can look for some of these areas where like,

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I just have an interest,

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I'm being pulled in this area.

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Maybe it doesn't make as much sense.

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And I'm not feeling that much resistance.

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And when you don't feel that much resistance in moving forward,

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that allows you to kind of keep progressing.

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Is there an area that you're feeling or what comes to mind for you as I bring that

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up about an area that's felt one way or the other?

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Yeah.

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So the area that I feel that pull towards is writing books.

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I love it.

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Yeah, I love it.

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And what does that look like?

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And don't use the but because we're throwing that out for a second.

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So tell me about what does that actually look like to you?

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That allows me to do more storytelling and more long-form writing.

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I'm working on two of these projects right now where I'm helping founders tell

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their story and their insights through a nonfiction book.

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And that just allows me to be more creative.

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Those are the conversations that I look forward to.

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That's what excites me the most.

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The exploration question here is how does that align with better financial sort of

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upside or abundance and this growth edge maybe of building a team?

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Like how are those things compatible?

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Just to explore.

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I don't know.

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How could they be?

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What makes them not compatible in your mind?

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I'm early in this book writing that I'm doing it for like very minimal money just

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to like prove the concept.

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And it takes a long time to write a good book.

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And so I don't see the like financial scale of

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as quickly as this other side of my agency that I've been doing it for longer and I

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just see like a quicker path to getting more clients and scaling that.

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That's what comes to mind.

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Maybe two options just real quick.

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One is that

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I think there's two ways you can look at this and probably many more, right?

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There's never just two, right?

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But one is I could build out this new product line.

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And this is just if you want to pursue this agency path, I can pursue this new product line.

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And that means other people can come in and support the existing product line.

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So myself as a CEO, I actually have gotten this part up and running.

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The only way to scale is to have someone else support that side of the business so

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that you can develop the next product.

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So that's one way I would see that that aligns, right?

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And that lets you pursue that, build it out.

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And so, yeah, maybe there is a less ROI for the business now.

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However,

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you're building out a new product that's going to add a new layer of ROI for the

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business.

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And so do you see what I mean there?

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Yeah, yeah.

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I've been thinking of them as like separate businesses or... They're both writing.

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They're both writing, similar audience.

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Yeah, so maybe it doesn't have to be.

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Even if it is all one,

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like I still want to be doing the book writing,

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but the other writing,

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I would be good hiring another writer or just managing that side of the business,

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doing the sales and the leads,

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but then hiring people to actually like do that.

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And that's a really clear pathway for a role and a step forward.

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One pathway is, hey, I've already got some clients.

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I can maybe have some leads.

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What happens if I don't if I'm not the writer for fulfilling that project?

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What would that do for my time?

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And I think in the context of our conversation,

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it's a pathway that you can step and you can unstep if you're not liking that.

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And what we talked about is aligning it with where your energy and curiosity is.

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You're having this energy for building up this other product line.

(00:19:17):
And so my mind goes to how much revenue is not being generated in this agency path.

(00:19:24):
by the book writing opportunities because you're not having time to spend there.

(00:19:28):
Because I'm not having time to spend where?

(00:19:31):
On the book writing.

(00:19:32):
Because you're spending your time here,

(00:19:34):
how much money is on the table in the book writing path for your business if we're

(00:19:39):
thinking about this as an agency or business that's not happening?

(00:19:42):
Or how many more leads would you close if someone else was supporting?

(00:19:45):
So all that to say, I think this is just one pathway, one option.

(00:19:50):
Does that make sense?

(00:19:51):
I've been thinking through this,

(00:19:52):
and I think it goes back to my black or white of like,

(00:19:56):
let's hear it.

(00:19:58):
I want to build this agency to sell in four years.

(00:20:03):
What does that look like to...

(00:20:06):
What makes you think that decision should be made right now?

(00:20:10):
It was like a logic optimized for financial stability goal of like,

(00:20:16):
if I want to back into this number,

(00:20:19):
let me like build this thing the right way.

(00:20:24):
So how could that part inform how you take a step forward that's aligned with where

(00:20:29):
you want to go potentially,

(00:20:30):
you know,

(00:20:31):
with an agency,

(00:20:31):
but just for this one step?

(00:20:35):
it's dipping my toe into it of getting that next client,

(00:20:39):
or it pushes me over my capacity of what I can do by myself.

(00:20:43):
Am I capable of bringing in enough leads to actually grow this agency?

(00:20:48):
Those are all unknowns that I think I can do,

(00:20:51):
but I need to take that first step to start trying.

(00:20:55):
And those are good growth oriented questions.

(00:20:57):
Like you like this personal growth.

(00:20:59):
You like betting on yourself.

(00:21:00):
You like having the option to kind of step back.

(00:21:02):
There's so much value in being in the experience of something over thinking through

(00:21:10):
the plan and,

(00:21:11):
you know,

(00:21:11):
architecting it all out.

(00:21:13):
And so I think if you've got some energy for it,

(00:21:17):
right,

(00:21:17):
which we talked about,

(00:21:18):
and you're able to get in the experience a little bit,

(00:21:22):
This takes us far away now from how are these other founders kind of building their lifestyles?

(00:21:27):
Like that's just so dependent on their own path or on business.

(00:21:31):
It's completely different for everyone.

(00:21:33):
Now you're getting this real information.

(00:21:34):
How do I, I love what you said.

(00:21:35):
How do I feel being a manager?

(00:21:38):
Did that go well?

(00:21:39):
And some people are like, Hey, this actually is, it's that green light.

(00:21:42):
You know,

(00:21:43):
it's like,

(00:21:43):
Oh,

(00:21:43):
actually add another client to their list at another client that like you might

(00:21:47):
find as you push into that,

(00:21:49):
it progresses.

(00:21:50):
You spend time in the chapter writing, you know, for the books.

(00:21:53):
Or maybe you find,

(00:21:54):
hey,

(00:21:55):
this is actually really challenging and I need to go learn some other skills or I

(00:21:58):
need to think about this more.

(00:21:59):
But I think a lot of the insight of the,

(00:22:01):
because now I want to bring it to the actual decision,

(00:22:03):
right?

(00:22:04):
Do I do this agency?

(00:22:05):
Do I stay solo?

(00:22:07):
What I feel,

(00:22:08):
and I'm curious how this lands for you,

(00:22:10):
is getting real information about the experience is what's going to help you with

(00:22:15):
that decision over planning an imagined future.

(00:22:20):
And also could take you a step farther.

(00:22:22):
Yeah, no, I think that that lands.

(00:22:26):
And like,

(00:22:26):
yeah,

(00:22:26):
I've experienced that even as I've grown this thing over the past year of I had

(00:22:31):
never done a sales call before because I was always just a consultant that got

(00:22:35):
handed the project.

(00:22:37):
And you can read all those books and whatever,

(00:22:39):
but it's not until you're like on these sales calls that I really learned and felt

(00:22:45):
what it was like and got better at it.

(00:22:47):
But

(00:22:48):
Yeah.

(00:22:48):
Yeah.

(00:22:49):
It's great.

(00:22:49):
You've got existing examples of how you've taken that step.

(00:22:52):
You know, I call it like the next vulnerable step.

(00:22:54):
It's like, it is a little bit scary.

(00:22:56):
It's a little bit different.

(00:22:57):
And when we have something good that's working, it's like, oh, do I want to break from that?

(00:23:02):
Because like, I feel good now.

(00:23:04):
I don't, I don't want to keep being vulnerable.

(00:23:06):
I don't want to keep putting myself out there.

(00:23:08):
And

(00:23:09):
I think when it becomes this big,

(00:23:12):
oh,

(00:23:12):
I'm now on this four-year journey to sail,

(00:23:15):
that makes that step even harder,

(00:23:17):
right?

(00:23:17):
Because now it all has to go right.

(00:23:19):
And so I think this just experiment,

(00:23:22):
this one project experiment or however you want to kind of bucket it,

(00:23:26):
that lets you take a smaller step,

(00:23:28):
experience it,

(00:23:29):
and takes you further down that path if you end up wanting to stay there.

(00:23:33):
Yeah, no, totally.

(00:23:35):
It's helpful talking through this.

(00:23:37):
I know this stuff,

(00:23:39):
but this kind of thinking is just so different than the way I was raised of like

(00:23:44):
getting the good grades,

(00:23:45):
going to a good university,

(00:23:47):
just like checking the next box up the ladder.

(00:23:51):
It's like having to like shift the mindset and it takes talking through this

(00:23:56):
multiple times to begin.

(00:23:58):
Yeah, two things.

(00:23:59):
One,

(00:24:00):
I'm going to pose the question that I think can be what you act on,

(00:24:04):
which is something like,

(00:24:06):
what is the one project or the next project that I can hire a contractor for to

(00:24:13):
help me out?

(00:24:13):
And that can be at any level or scale.

(00:24:15):
It could be part-time help, whatever.

(00:24:18):
And I imagine there's actually a project there like now-ish.

(00:24:20):
Like I imagine there's something close.

(00:24:22):
So that's what I'd leave with.

(00:24:23):
I'll follow up and email you that.

(00:24:25):
I think that's kind of the action question.

(00:24:27):
You bring up one last thing that I'd love to explore with you a little bit here,

(00:24:31):
which is I think what I'm hearing you say is there's an identity that has been

(00:24:35):
built around this other method of growth that is more structured and ladder

(00:24:40):
oriented.

(00:24:41):
And there's a new identity,

(00:24:42):
a new hat you're kind of putting on that operates in a different world.

(00:24:47):
And so it might be hard to define right now,

(00:24:51):
but kind of understanding how you're telling yourself a story about who you are.

(00:24:56):
I think the more actually you can write out,

(00:24:58):
like this is who I thought I was on that path,

(00:25:01):
but actually this is who I am.

(00:25:06):
Defining like the name for that or the qualities or traits of that and seeing them

(00:25:12):
side by side,

(00:25:13):
I think will help you shift into that.

(00:25:15):
You know, who did I have to be?

(00:25:19):
And who do I either want to be or who am I or who am I now?

(00:25:22):
I want to tell you quickly why I'm saying this.

(00:25:26):
And I've seen it in a lot of agencies specifically,

(00:25:29):
founders who've grown agencies and broken through multiple growth points.

(00:25:34):
It's like as soon as the founder sees himself in a new way,

(00:25:37):
you know,

(00:25:38):
I'm a solopreneur,

(00:25:39):
I'm a business owner.

(00:25:42):
Their thinking changes, the lens changes.

(00:25:44):
And it takes a while to get into that spot.

(00:25:48):
but it does make a big difference when you sort of re-categorize your identity.

(00:25:52):
And it just takes deciding that and seeing that for yourself.

(00:25:55):
Oh, yeah, I'm a business owner, not a solopreneur.

(00:25:58):
Whatever words make sense from the old path to the new path,

(00:26:01):
I think is more what I would focus on.

(00:26:03):
Okay, cool.

(00:26:04):
Yeah, no, thank you for that.

(00:26:05):
I'm excited to journal on that.

(00:26:07):
Yeah, I think I could take it a lot of ways.

(00:26:09):
The one thing that came to mind immediately was this experimental mindset of being okay with

(00:26:16):
Like,

(00:26:17):
I mean,

(00:26:17):
what we got to,

(00:26:18):
yeah,

(00:26:18):
just like try the next thing and pivot and fail or whatever you want to call it

(00:26:24):
versus like that was just so different in the other path of it's just like this is

(00:26:29):
the list of things you do to get to the next level.

(00:26:32):
Yeah,

(00:26:33):
it's like the experimenter is like dynamic and thinking doesn't have these super

(00:26:37):
long term plans because you can't,

(00:26:38):
you know,

(00:26:39):
perfectly plan everything out in the future.

(00:26:41):
Right.

(00:26:41):
You're going to feel how it actually is.

(00:26:43):
You're going to see what works like.

(00:26:44):
Yeah, that's where you can detail the experimenter versus whatever the previous thing is.

(00:26:50):
Cool.

(00:26:50):
Yeah.

(00:26:51):
Last thing, does a word come to mind for the other side?

(00:26:53):
There's the experimenter and there's the experimental process and there's the,

(00:26:57):
what would the old style be?

(00:26:59):
Follow the path or something like that.

(00:27:02):
Right.

(00:27:02):
Yeah.

(00:27:03):
Keep following the path of others or something.

(00:27:05):
Yeah.

(00:27:05):
Something like that.

(00:27:06):
Cool.

(00:27:07):
Yeah.

(00:27:07):
Well,

(00:27:08):
I will send you a follow up with that question because I think that's,

(00:27:11):
but that's really what I would encourage you to look for.

(00:27:14):
And thanks so much for jumping on and talking about this.

(00:27:17):
Yeah, no, I really appreciate it.

(00:27:19):
Great questions.

(00:27:20):
And I'm excited to see you do this with a lot of other people as well.

(00:27:25):
Thanks.