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Step inside real founder conversations: raw, unrehearsed, and honest. No playbook. No polish. Just ambitious entrepreneurs uncovering the answers that were there all along. Because every business hides something valuable trapped under the weight of success and chaos of growth.
The Hidden Value podcast is hosted by David Sherry. David works with early-stage founders to grow professionally and personally. He founded, sold, and advises Death to Stock – a media company and newsletter that serves brands like Unfold, Figma, and Spotify.
(00:00:01):
Latham, thank you so much for being here.
(00:00:03):
I'm excited to dig in on today's episode.
(00:00:07):
I think a great place to start is getting a little bit of an understanding,
(00:00:11):
quick background context.
(00:00:13):
What chapter do you feel like you're in in your life?
(00:00:17):
Yeah, the chapter question is a really hard question.
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It's a high number, maybe is the way to say it.
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If you had to name it, what would you title the last chapter?
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And then what's this chapter titled?
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I think the last chapter was...
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I mean, maybe the way to title it is just like going deep or figuring it out.
(00:00:37):
Like the last year and a half was really focused on family, especially my son.
(00:00:43):
I started homeschooling him a year and a half ago.
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And so the last year was literally just like
(00:00:49):
figuring out what does it mean to be in charge of the education of another human being?
(00:00:54):
How do you do that?
(00:00:55):
What's kind of fact from fiction?
(00:00:57):
I always had this feeling that education as we did it as a society was suboptimal at best.
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I think that's been the last year,
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has been figuring that out and going deep and really understanding education as a
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product or as a service.
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And as a parent.
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And as a parent, yeah.
(00:01:14):
And coming out of that is now...
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There's a desire to build a business,
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build a reputation,
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actually get out and take those ideas and put them into the world in a way that can
(00:01:27):
support other parents that can,
(00:01:29):
quite frankly,
(00:01:30):
make some money.
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Because homeschooling is very underpaid, to say the least.
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Right, yeah.
(00:01:35):
And then shifting out of like, okay, I'm an expert with my own kids.
(00:01:39):
How do I take that experience from
(00:01:43):
and build on it in a way that builds my reputation,
(00:01:46):
builds the business that I want that can do good in the world.
(00:01:50):
Totally.
(00:01:51):
Yeah.
(00:01:52):
Am I hearing that you want more learning?
(00:01:54):
Like you did it in this one context and how do you expand that learning and monetize it as well?
(00:02:00):
Yeah, I think so.
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I mean, I would consider myself a lifelong learner.
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It's something I want to model for my kids.
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So it is very important to me.
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I don't always feel like I'm contributing to the family financially as much.
(00:02:14):
Sure, totally.
(00:02:15):
A lot of stress on my wife and my family because of that.
(00:02:18):
So I'd say an equal part as much as continuing to learn, continuing to grow personally.
(00:02:23):
Yeah.
(00:02:25):
Yeah, you've already done a lot of that deep dive learning and now it's the other side.
(00:02:28):
It's like, okay, let's transition into the monetization of that learning.
(00:02:32):
Something that comes to mind to me, and it's actually a David White quote.
(00:02:36):
I don't know if you know that poet,
(00:02:37):
but he has this idea of sort of start close in,
(00:02:39):
meaning start with the step that's available next to you.
(00:02:43):
Like, what is that?
(00:02:44):
I think the first step is easier when it's close.
(00:02:47):
Yeah.
(00:02:47):
Right.
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And who do you know?
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What parents have you already talked to that might, if aware of what you did, be interested?
(00:02:55):
You know, that's a curiosity of mine.
(00:02:57):
Yeah.
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It's a great question.
(00:03:00):
The longer term vision is broader than my local community.
(00:03:05):
It's not a scale, right?
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Like I don't want to grow a, I don't want to put a million students through.
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I would love to work with
(00:03:12):
100 students over the next 10 years, or 100 learners and families.
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But part of it is like,
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I live in Montana,
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and I love it here,
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but there's not probably 100 students and 100 parents that really want to take that
(00:03:28):
leap.
(00:03:28):
I can think of maybe one that I know locally.
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But the fact of where I live limits some of what is possible.
(00:03:41):
Got you.
(00:03:41):
Yeah.
(00:03:42):
Okay.
(00:03:42):
So part of the challenge is how do you find, I love this structure now, right?
(00:03:47):
100 learners.
(00:03:48):
That's a really clear structure to kind of look at and say, okay, I can handle that, right?
(00:03:54):
And so the challenge, which is okay if there's a challenge, just to say it is,
(00:04:00):
I want to work with 100 learners.
(00:04:02):
And is my location going to be supportive of that?
(00:04:07):
That's the push and pull to block a little bit there.
(00:04:11):
And do you feel like that question has blocked starting the conversation with that
(00:04:18):
one family or being in the practice of talking about it in a service business
(00:04:23):
oriented way?
(00:04:24):
Have you had those conversations?
(00:04:27):
I have danced around the conversation.
(00:04:30):
Yeah.
(00:04:31):
It's taken me a long time to get to the point where I'm like,
(00:04:34):
okay,
(00:04:34):
I'm ready to have this conversation.
(00:04:36):
Love it.
(00:04:36):
A lot of like dancing around and kind of trying to approach it from a hundred
(00:04:40):
different angles that aren't me just saying like,
(00:04:42):
Hey,
(00:04:42):
I want to do this.
(00:04:44):
Is this something you'd be interested in?
(00:04:45):
Yeah.
(00:04:46):
What's wrong with saying that?
(00:04:47):
That's such a great way to, that's such a great way to start that conversation.
(00:04:51):
What's, what's wrong with that statement?
(00:04:53):
What about that?
(00:04:54):
I mean, now that I say like, now that I tell you the answer should be nothing.
(00:04:58):
I think like,
(00:05:00):
It feels very personal.
(00:05:02):
It feels like in the moment, it's kind of the same reaction.
(00:05:07):
I have this imagination of him saying no and being like,
(00:05:10):
he's rejecting everything that I've done for the last year,
(00:05:13):
which I know is completely irrational.
(00:05:17):
But every time I like think about having that,
(00:05:19):
I have that kind of sensorial reaction,
(00:05:22):
if you will.
(00:05:22):
Yeah.
(00:05:23):
So, okay.
(00:05:24):
So what if instead,
(00:05:26):
what I'm hearing is that all this learning you've done,
(00:05:29):
it can,
(00:05:30):
and I totally get this feeling,
(00:05:31):
it can feel like it'd be invalidated or something like that with this one decision.
(00:05:36):
Yeah.
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And I think that can happen, sort of.
(00:05:41):
I don't think that's really what would happen.
(00:05:42):
But it could kind of happen if you've set it up so that that is what happens, right?
(00:05:47):
That I'm going to make this really clear ask.
(00:05:49):
It's going to be really clear yes or no.
(00:05:51):
And it's going to A or B, you know, discredit everything or whatever the feeling is.
(00:05:55):
And so I wonder about enrolling this person in learning about their reaction to it.
(00:06:04):
And so you could be even more open and just say, I've been doing this practice and learning.
(00:06:08):
I'm interested in exploring whether this is something valuable.
(00:06:12):
Could I learn your perspective or could I get your feedback?
(00:06:16):
Could you enroll them so that it's not A or B, yes or no?
(00:06:21):
It's more, I'm trying to understand how this lands for you.
(00:06:24):
I'm trying to see what you see as most valuable.
(00:06:29):
that may progress the conversation to be a different frame.
(00:06:33):
You can still say,
(00:06:34):
I see this as a business and here's what I'm thinking about charging even,
(00:06:38):
but there's no rejection opportunity in the same degree.
(00:06:43):
That makes a lot of sense.
(00:06:45):
I do think that would be,
(00:06:47):
I don't want to say a lot easier because it's still an easy conversation,
(00:06:51):
but it would feel a lot less personally invalidating,
(00:06:56):
personally
(00:06:57):
Threatening is not quite the right word, but that's the word that comes to mind.
(00:07:01):
I think it makes sense that at this time, the two things feel intertwined, right?
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Like you and the learning and the product.
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And so that's what's on the chopping block, let's say, you know, for this conversation.
(00:07:15):
I think what I've found in,
(00:07:17):
and I've sold services for a long time now,
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is the more I put my attention on them,
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You know, the more I'm sort of looking at them, listening to them, what are they saying?
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How can I learn from what they're saying?
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The less I'm sort of thinking, what are they seeing about me?
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You know, are they validating my ideas?
(00:07:36):
And so getting curious about them,
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asking them questions,
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asking them if you could get coffee to ask them questions and pose it that way
(00:07:44):
versus pitching.
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I think pitching...
(00:07:46):
itself maybe creates a bit more of that pressure dynamic of I need to say the right
(00:07:51):
thing the right way to get the validation or to get the yes.
(00:07:56):
So maybe interviewing, asking questions.
(00:07:59):
Yeah,
(00:07:59):
I'm curious in your experience,
(00:08:01):
when you do that well,
(00:08:03):
how much of an idea of the product or the service or the story do you already have?
(00:08:09):
Or is it more like, I know I have these eight questions, for example, where on that line
(00:08:16):
are you balancing between not selling,
(00:08:19):
but also making sure you get the validation of the information you need?
(00:08:24):
Yeah, yeah, I think this is a really great question.
(00:08:27):
I would say that I'm trying to first,
(00:08:33):
before I can offer something of value to somebody,
(00:08:36):
I like to understand if what I'm selling to them might be needed.
(00:08:43):
And so I wanna understand some questions about what challenges they might be
(00:08:47):
facing,
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what context they're currently in,
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so that my pitch
(00:08:54):
after the fact, matches what they need if they're the right fit for me, right?
(00:08:58):
So let's just imagine that you're talking, and we can maybe play this out, right?
(00:09:02):
You're talking with this person.
(00:09:03):
Is it essentially homeschooling services that you want to sell?
(00:09:07):
It's more like in-person learning experiences.
(00:09:11):
Yeah, okay.
(00:09:12):
It could be a full homeschool, but like,
(00:09:15):
you know,
(00:09:16):
these kind of six weeks long experiences with their kids and ideally with parents
(00:09:21):
too,
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but I know that that's sometimes a harder lift.
(00:09:24):
So this idea becomes a question, right?
(00:09:28):
Have you ever paid for learning experiences with your kid?
(00:09:36):
Have you ever invested in this type of product?
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Maybe something a little bit similar.
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What do you do when you find yourself with six weeks in the summer and there's no
(00:09:45):
curriculum,
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but you still want your student to learn?
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You can take some of those ideas and turn them into questions where then they can
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tell you where they're coming from.
(00:09:55):
What do you spend?
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Where do you spend the most money when it comes to your students' education?
(00:10:04):
What have been the best experiences,
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you know,
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when your kid comes home and says they had the best experience ever?
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What was that like?
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And I think kind of where we're getting now as well is whether you're needing to
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educate people on a new type of product or whether this is a product that they're
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familiar with.
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So, but I want to pause.
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Does that kind of making sense is that...
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Yeah,
(00:10:28):
just use questions that allow you to understand a bit more of how they would
(00:10:33):
describe these things.
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That sounds so much easier than like,
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I designed this incredible thing and now I'm just going to sell it to you,
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which I've been more than guilty of.
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Something just came to mind to me, which I think is a really common challenge.
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When you're marketing online,
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or you're writing a book,
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you're creating something that is meant to be read by thousands of people who will
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never meet you.
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When you're selling an individual service to an individual in your community,
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you're having a conversation with somebody that you know or don't know,
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but you're in a conversation with them.
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A conversation can be more spontaneous, can be more connected, more relational.
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It's way less pressure.
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I think if you were writing, yeah, copy for like a marketing page,
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there is more refinement kind of needed there because it's,
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you don't know who's going to come across.
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It needs to nail every word and all the, you know, this is not, I think this is not like that.
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This is the benefit in some ways of the personal work that I think you want to do.
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Yeah.
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Yeah.
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That resonates a lot.
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I love having conversations with people.
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I hate selling,
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but I love having conversations with people and I'm at my best one-on-one with
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another person.
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Yes.
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So one-on-one,
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you don't need all those materials necessarily because you are learning and
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connecting and maybe you hear something about what they're wanting.
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Oh, I think we only have a week, not six weeks.
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Like that's information for you.
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Okay.
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Maybe, maybe I think about that maybe, or maybe you don't, maybe you push forward.
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Right.
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But you can be a little bit more dynamic in the conversation.
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Yeah.
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That's cool.
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I appreciate that quite a bit.
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Yeah.
(00:12:14):
Something else that might help is this category.
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Is this something that people are used to buying?
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I don't know how clear this feels to you, but that's a question that now pops up for me, right?
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How do they know what they're buying?
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The model I have of what they're buying or what we're kind of competing for time
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and attention and money with is
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after-school enrichment programs, at least to start.
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Long-term,
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I would love for this to be a full-time school or a community,
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but the easiest way to get the idea out there is comparing it to an after-school
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enrichment program where you can either take your kid,
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I don't know,
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like go horse riding,
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or you can come do this for the next six weeks and see what that's like.
(00:12:56):
So now I'm curious because you said,
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I think there's only one person I can think of maybe who fits this.
(00:13:02):
I was thinking this is like full-on homeschooling.
(00:13:05):
Right.
(00:13:06):
And you're saying it after school.
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Let's ask the question.
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Let's re-ask.
(00:13:13):
Is there one person?
(00:13:15):
Where is that coming from?
(00:13:16):
Yeah, you got me.
(00:13:19):
I'm not meaning to put you on the spot about it.
(00:13:22):
I'm really just curious.
(00:13:23):
I might want this actually.
(00:13:27):
I think to your point,
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yeah,
(00:13:31):
I could probably find 10 parents to do a first learning experience in our local
(00:13:36):
community pretty easily.
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Yeah.
(00:13:39):
That also takes the pressure off here a little bit now because now it's 10 conversation.
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There's learning in each,
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you know,
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or maybe it's more than 10 and some people join,
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some people don't.
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It also removes a little bit of that
(00:13:51):
A or B, this exists or not.
(00:13:53):
How will they find,
(00:13:54):
in talking with them,
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like there's this extra benefit that could emerge for you,
(00:13:57):
which is now you have 10 people who you can talk with about this.
(00:14:01):
I don't know, maybe that's, and so it's 100 students, 10 parents who are super energized.
(00:14:07):
You know, that's possible for sure.
(00:14:09):
And so I think these conversations create the opportunity for that to potentially exist.
(00:14:17):
So the question around selling too now is like,
(00:14:19):
you know,
(00:14:20):
how much do I need before I go into sell?
(00:14:21):
You asked me that question.
(00:14:22):
That's actually, you got the first experience.
(00:14:24):
So that's dialed too.
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I think part of that is having the first experience and writing this all out gave
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me that feeling of like,
(00:14:31):
oh,
(00:14:31):
if I get rejected,
(00:14:32):
they're rejecting mine.
(00:14:35):
But I've also like, I've talked to at least five parents who said, this would be really cool.
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Like we'd love to enroll our kids.
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And somewhere between knowing that and feeling like there's one person who like,
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it's fully aligned on the overall vision.
(00:14:50):
I, uh, I very much have gotten myself stuck.
(00:14:56):
It's understandable.
(00:14:56):
It's meaningful work when you,
(00:14:59):
start to work on things that are more meaningful to you and you've invested a lot
(00:15:03):
of personal time in this learning I understand how that can be something that the
(00:15:09):
inclination is to kind of okay I don't know if I can really like show this off too
(00:15:13):
much because you know and I I do I do feel that the flip side is also available
(00:15:21):
which is
(00:15:22):
here's this thing I'm finding kind of cool and interesting.
(00:15:25):
And as I'm sharing it, there's actually more people, right?
(00:15:28):
It actually can go the other way where it's like more interesting conversations
(00:15:32):
with more people.
(00:15:34):
more experiences you get to have expanded learning and,
(00:15:38):
you know,
(00:15:38):
to bring it back to,
(00:15:39):
I think what's important to you is also a path to income.
(00:15:43):
So in this,
(00:15:45):
I think we need to keep that really present because the other parts that can feel
(00:15:50):
good,
(00:15:50):
that are a little less scary in some ways of,
(00:15:53):
you know,
(00:15:54):
having payment.
(00:15:55):
And so what that means is somewhere in these dialogues,
(00:16:01):
It's off track if there's not some aspect of it's a learning program after school.
(00:16:07):
Here's the first one.
(00:16:09):
I'm thinking it's X dollars,
(00:16:12):
you know,
(00:16:12):
or I'm taking registrations for early signups or any early signups or X dollars.
(00:16:18):
That's that is part of the validation.
(00:16:20):
Yep.
(00:16:21):
And part of the conversation.
(00:16:23):
I've I mean, when I wrote up this thing, it says in there, like, this is a
(00:16:28):
premium experience for children and it's $300 for six weeks.
(00:16:34):
I even have a link to Stripe to accept payments.
(00:16:39):
Okay, great.
(00:16:40):
Yeah.
(00:16:40):
So I've gotten as far as I can without like actually having conversations.
(00:16:44):
That's awesome.
(00:16:45):
Great.
(00:16:46):
So I think the path here is conversations, right?
(00:16:49):
So I'm sort of, I'm expanding on this path that I want.
(00:16:53):
If I'm having these types of conversations,
(00:16:55):
the ones we're talking about,
(00:16:58):
and sounds like there's maybe 10 people in that orbit already.
(00:17:02):
I think so.
(00:17:03):
To start with.
(00:17:04):
Yeah.
(00:17:05):
And each one's such a learning opportunity too, you know?
(00:17:08):
Yeah, that feels right.
(00:17:11):
I mean,
(00:17:12):
it feels like viewing it as a learning opportunity and as a way to not get feedback
(00:17:18):
on my idea as much as just see what people value and where it's aligned and where
(00:17:24):
it's not aligned feels a lot easier.
(00:17:27):
It definitely feels like the next step.
(00:17:34):
Totally.
(00:17:34):
And including,
(00:17:35):
you know,
(00:17:36):
I'll just say this again,
(00:17:37):
including the payment part at some point that it structurally needs to be there for
(00:17:41):
this progress to work for you.
(00:17:43):
You sort of have to leap for other people to leap.
(00:17:46):
And I don't know if when this will feel right, but having a schedule or
(00:17:53):
When it begins,
(00:17:54):
there's a moment where I think you might want to think about,
(00:17:58):
it starts on this day.
(00:17:59):
I'm having these conversations now.
(00:18:01):
And that way you're telling them that it's coming up, it's starting.
(00:18:05):
People will feel that commitment.
(00:18:06):
If you're too exploratory, there's no boundaries.
(00:18:09):
It might happen, it might not happen.
(00:18:12):
It's not like grippy for people to actually decide yes or no, pay yes or no.
(00:18:17):
A start date can also be a very powerful tool for your own commitment and for theirs.
(00:18:22):
Okay.
(00:18:23):
Would you recommend having conversations before a pick-to-start date?
(00:18:28):
Yeah, I think a conversation or two could help you feel more comfortable.
(00:18:34):
You could circle back up with those people with a date.
(00:18:37):
What I'm really saying is that
(00:18:40):
There's this commitment.
(00:18:42):
There's this aspect of commitment that you are asking of them with payment.
(00:18:47):
It could be a quick conversation or two and maybe you get them to pre-order and
(00:18:50):
then you set the date.
(00:18:53):
But that will add structure that will help more people decide.
(00:18:56):
It'll be for your benefit as well.
(00:19:00):
Any reflections or anything else you want to share here or questions before we wrap up?
(00:19:07):
I mean, it sounds, as I hear us talking about it, I'm like, why couldn't I figure this out?
(00:19:12):
I was in the Navy and we always had a term.
(00:19:15):
If you can't figure out your own shit, somebody else is going to show it to you.
(00:19:18):
It's, uh,
(00:19:18):
It's super helpful.
(00:19:19):
So I really appreciate that.
(00:19:21):
Great.
(00:19:22):
Yeah.
(00:19:23):
I, yeah, it's, it's, it makes sense, right?
(00:19:26):
It's just this,
(00:19:26):
it is this little line in the sand you're kind of stepping over into and,
(00:19:31):
but I think once you do that,
(00:19:32):
then you'll,
(00:19:33):
you'll feel,
(00:19:33):
okay,
(00:19:34):
this is actually,
(00:19:34):
we're,
(00:19:35):
yeah,
(00:19:36):
moving forward.
(00:19:38):
Yeah.
(00:19:38):
I'm, I'm excited.
(00:19:40):
Awesome.
(00:19:41):
Well, thank you so much.
(00:19:42):
And yeah, I can't wait to hear about how, how things go.
(00:19:46):
Thank you.
(00:19:46):
Me too.
(00:19:47):
Awesome.