Jul 10, 2025
Tim He checks many boxes as a guest on the Founders Sandbox- a 3x founder, now advisor, professor, creator, writer and coffee snob. Tim’s newsletter, "Cherrytree", allowed him to keep teaching entrepreneurship while the pandemic closed the classroom. By providing a newsletter, Cherrytree now offers consulting and coaching to cofounders. In Tim's own words; "I want to actually change how people become cofounders. And then how they stay cofounders."
It is a tough decision to “divorce a co founder” and we find on this episode with Tim He sound advice on getting the pre nuptials in place for just in case scenarios and preventatively preserving the co founding team dynamics.
Listen to this month’s episode “Choosing the right Cofounder” on The Founder’s Sandbox with Tim He.
You can find out more about Tim at:
https://www.linkedin.com/in/timhe2000/
https://www.dumbfoundcoffee.com/.
Transcript:
00:04
Good morning. Welcome back to the Founder's Sandbox. I am Brenda
McCabe, your host on this monthly podcast now in its third season.
The Founder's Sandbox is a podcast where my guests are
00:33
business owners, founders, professional service providers and
corporate directors. And we all share a mission and we find
ourselves speaking here on the Founder Sandbox. This mission
is really to work through the power of the private
enterprise, be it small, medium or large, to create change for a
better world. And each of my guests tells a story, right? The
origin story.
01:03
that touches on the topics that I'm so passionate about resilience,
scalable, purpose-driven enterprise, all with good corporate
governance. And we do this in a fun sandbox environment here
in the Founder Sandbox. I am absolutely delighted to
have as my guest today, Tim He. He is joining us from
Dallas, Texas today. And Tim.
01:33
is he's going to be speaking to us. He checks a lot of boxes,
but today he's going to be speaking from his experience as an
advisor to pre-seed and seed companies. And we share a common
kind of subject matter expertise. We work with a lot of
founders that are seeking to find a co-founder or we're working
with them to how to divorce a co-founder, which
02:01
Nobody likes to talk about this, but it happens more frequently
than not. Matter of fact, Tim has chosen for this episode, the
title of Scaling Your Co-Founder Relationship. So Tim,
welcome to the Founder Sandbox and thank you for joining me today.
Thanks for having me. This is gonna be a lot of fun because the
thing with co-founder relationships is that when it's
bad,
02:28
It's bad. You you think of divorce, arguments, sometimes even
litigation, but when it's good, it's pretty magical. You build very
valuable companies that change not just your lives, but the world.
And it creates a type of team and culture and company
that people want to root for. And when I get to see that,
that's the best part of my job. And it's actually
pretty magical. It's very fulfilling, isn't it? It is.
02:55
So you check a lot of boxes, but we're going to focus on that. You
are a founder yourself, prior founder, advisor, creator, writer,
and coffee snob. So we'll get to your love of coffee later in
the podcast. When you reached out to me, it did kind of
make me giggle because nobody likes to talk about divorce,
right? Let alone your co-founder.
03:24
And you specifically reached out to me because the work you
do and your platform at Cherry Tree is around
co-founder, choosing the right co-founder and the like.
I have experiences with my clients on making that
tough decision to divorce a co-founder. And I read some of
your blogs.
03:52
And you do provide sound advice on getting what I call the
prenuptials in place. So kudos to you. And more in the
podcast today. So I love what I do, right? And my
consulting firm where I advise kind of scaling companies to
work with them on purpose and resiliency.
04:21
advice to founders when working at Cherry Tree and finding the
right co-founders, scaling it that, it doesn't crack under startup
pressure. It's probably rot with your own origin story as founding
a company. Can you share that with us here, Tim today? Of course.
Yeah. I'd say almost 10 years ago now, I started a company with
five other co-founders. So six of us in total.
04:51
which is pretty unconventional in the sort of software
startup ecosystem, but it wasn't intentional on my part. I
was in college at the time and I was thinking, you know, I want
something to do other than homework. So I found a bunch of my
friends and asked them if they wanted to start a company with me.
And I didn't expect them all to say yes, but they all did.
And so we were like, sure, let's just do something together.
And that was sort of the beginning.
05:21
And you were six co founders. Yeah. And let's
carry on. That's good. That's unconventional. It was a lot,
but it was a lot of fun. You know, I was best friends with some of
them. And then some of them were mutual friends or classmates that
I met in school. And so they also had different relationships with
each other. Not all of them knew each other in the beginning. All
of them knew me.
05:49
but to varying degrees as well. And so I kind of got to see the
entire spectrum of what a co-founder relationship can be. And
at the same time, I was teaching entrepreneurship in Seattle and a
lot of my students would ask me the same questions about
co-founders. You know, the basics like how do you split
equity? How do you choose titles and roles and
responsibilities? How do you fight with each other
productively?
06:18
All those things that me and my co-founders were going through at
the same time. And so we made a decision to be very open and
transparent about it. I shared with my class how I split equity
with my team and the reasons behind it. And I shared with
them what we debated about on the product side or the marketing
side and how we came to a resolution. And so the students had a
very behind the scenes look at what goes on with
co-founders.
06:47
And then COVID hit. And so I started writing online for my students
quite a bit. And then over time that became a book about
co-founders. And then when I published the book, you know, more
people started reaching out to me, but it wasn't just college
students anymore. was people with venture backed companies,
companies going through YC and all sorts of industries all over the
world. And then somebody was like, Hey, I don't want to read
a 200 page book. I want something quick.
07:16
something easy and actionable. And so that's how I got started with
the Cherry Tree newsletter, which comes out every Monday and
Friday. And it's nice and easy. It's very relatable and
actionable. And then people started replying to the email
asking for personalized advice because they said that, you know,
500 words is not enough to solve a tricky situation. And
that's how I got started with co-founder coaching. And so now
07:46
the Cherry Tree Company as an umbrella, comprises of the
newsletter, which is free. And for people who are maybe just
starting out and want to build good habits, and then also the
coaching component as well, for people who are either going through
some high growth stage, like raising a fund or going
through a major pivot, or they just want to talk about
some concerns or curiosities they have about co-founder
relationships. Let's go back to your
08:16
co-founder, your six co-founders. that company still exists
today? What was the, so what was the outcome? Yeah. It was a
software company in the real estate space. And so COVID kind of
took us out, but it didn't take out the friendships. We are all
still best friends and visit each other over the holidays. In
fact, when I, when I move in a couple months, I'm moving to a
city where two of them already live right now and
08:43
One of the things I looked for was an apartment that was close to
them so we could all hang out together. COVID took out the company,
but not the co-foundership. All right. You did speak about the
newsletter. why did you choose that medium? And again, I think you
said there are typically 500 words. I've read a few of them. I blog
myself. And we shared a couple of our blogs back and forth.
09:12
reached out to me, said, oh, I've written about that, and how
to split equity and the like. So what made you choose the
medium of a newsletter?
09:25
Yeah, I mean, I've always liked writing. think it makes me, it
forces me to think very hard and clearly about what I wanna
articulate. Back when I was teaching, I found that I would have a
topic or a concept in my head, but when I went to explain it to
somebody, I couldn't quite articulate it the way that I felt,
especially when they started asking very thought-provoking
questions. I felt I was stumbling. I felt that I...
09:52
had an answer in my head, but I couldn't quite deliver it to them.
But, you know, because we all went remote, I was writing for them
and that was a forcing function to get everything crystal clear.
And that became a really good habit for me. Plus I've always
liked reading. I follow several other newsletters as a
reader, as a customer of theirs. And so I've always been intrigued
by it.
10:16
And then one of my friends who is at a private equity firm
specifically focused on newsletters was telling me a little bit
about the backend of newsletter businesses and the unit economics
for it. And I realized it was a very viable and very scalable
business opportunity. And so I thought I would do this practice
because it's good for my own just thinking process.
10:42
And I get to update it every every week, twice a week with new
information that I find. And so a newsletter kind of just
made a lot of sense. Excellent. And then the show notes later,
we'll put the the URL is it cherry tree dot v hi.com,
right? We had to access your newsletter. So teaching
11:09
you're teaching in a university in Seattle,
entrepreneurship, you're so young, it's amazing. How did you
get into the teaching position? I got very lucky. on
my first, sorry, on my second quarter of college, I was
working retail in the mall selling glasses. And it
was
11:38
at about 9 p.m. right before we were closing and a customer walks
in and you know how it is. Nobody wants to deal with a customer two
minutes before closing. I'm a new kid so the manager is like, you
go talk to them, get your practice. So I go and I talk to the
customer and we just make small talk. I'd tell him that I wanna get
into business school. want to...
12:04
be a part of startups and all this exciting stuff. I was 18 or 19
at the time. And he was like, hey, you should talk to this
professor. He teaches at the business school as an
entrepreneurship professor. And I think you guys will really
get along. So he wrote down this professor's phone number. that was
it. He didn't buy any glasses. We closed the shop and I walked
home. I didn't think much of it. I was trying to make a
sale.
12:34
I had that note in my pocket and when I got home, this was
maybe around 10 PM, I was changing out of my work clothes and
I had that note and I thought, hey, maybe I should give this
professor a call and his name is Alan. And so maybe I
was naive or impulsive, but I called him at 10 PM with no
forethought. I didn't think, hey, maybe I should email him or call
him tomorrow morning. I just had the note in my hand and I was
like, let me just call him and he picks up.
13:04
And we talked for about an hour and a half. Oh my goodness. About
the, yeah, about the classes he's teaching, about how he became a
professor and his alumni. And it was very clear to me
that he loved teaching. He was in his late fifties, early
sixties and independently wealthy from running his own
companies. He had retired for a number of years and then come back
to teach because he just loved teaching. And so.
13:34
I was like, hey, can I take your class? It sounds really cool. But
the administration was not happy with that because I was a freshman
and he only taught senior classes. And I was not only not in the
business school, I had not taken any of the prerequisites and the
class was already overbooked. Oh my gosh. So. We were all stacked
against you. Exactly. But he said, just come to the classroom at
this time and sit in the corner.
14:01
Like you might not get credits for the class, but just sit in
the corner and pay attention. And so I did that and I started
answering questions in class. Questions that some of
the upperclassmen may not necessarily have been able to
answer, which was very surprising to me because I had never done
well in school. Throughout high school, I barely got into college.
My parents were on me all the time, but this was the one class
where I felt like I knew what I was talking about.
14:31
And so I went to all of his classes and eventually became his
assistant. And that slowly changed. And I,
was an assistant for about 30 courses and then later become a
co-instructor at both campuses. And so I got really
lucky. It was unconventional, but this, this mentor, Alan
sort of gave me that opportunity. And I finally felt like I, I was
doing something that I was good at.
14:59
Amazing. That's an amazing story, very unconventional, but I
love that. You heard it here on the founder's sandbox. My
guest, Tim He, got into teaching, and then eventually COVID
hit. You started continuing to teach virtually and started
providing your content through a newsletter and your regular
postings two times a week. So bravo.
15:30
You also have time to run another business. I introduced you with
many titles, but you are a coffee son of so what is it with the
coffee, Tim? Yeah. All right. You taught up in Seattle, right? And
we all know he's from Seattle. But what is it about the coffee and
it's called dumbfound coffees? Yes, yes. It's a fun story. It's
quirky. I
15:59
A couple of years ago, I helped this coffee
founder a little bit with his business. was my friend
and I helping this one man show. He was bagging the beans by
himself, sealing it, weighing it, driving it in his truck to the
post office, handwriting notes for everybody. And he also had
a day job. So he was doing this on top of that. And he had a wife
and four kids. And so he really needed some more extra hands.
And so
16:29
We started with helping him literally just bag beans. And then
we got to understand the coffee business and how to
market coffee, how to optimize shipping and logistics to save
on costs and sort of everything in between. It was really
fun. And my friend and I always joked that we would start our own
coffee company. And then right after working there, I went to work
at a very large coffee chain, global chain, strategy
team.
16:58
And that was very different because there are thousands of people
at this company with billions of dollars in budget. And so I saw
this industry from a completely different lens. Right.
And it was very interesting because there are so many
similarities between this, you know, global corporation and a
one person coffee shop. And of course I love coffee. I've
been drinking it for
17:25
as long as I can remember drinking a little bit, a little sip of my
mom's coffee when I was a kid. I'm Canadian. So I grew up drinking
Tim Hortons for those of you Canadians out there, know what it is.
so I love Tim Hortons. It's so good. Tim Hortons. Yeah. And of
course, you know, Tim and Tim, so I have to get it from them.
17:51
Uh, but yeah, fast forward, uh, three or four years now, my friend
and I got in touch again and we said, Hey, let's start a coffee
company. Uh, we've been wanting to do this for years. We've,
we finally have the circumstances and sort of the, the, the
personal financial, uh, privilege to do this now. Um, let's,
let's get something up and running. And so we're thinking, how do
we differentiate? There's a billion coffee companies out there.
Um, there's coffee for, for veterans, for teachers, for
18:21
hippies for everybody, except for founders. And founders
drink a lot of coffee. I'm a three time founder. My friend
was also with founder and we drink a lot of coffee. My friends
drink a lot of coffee. And there's something satisfying about
having a cup of coffee and sitting down at your desk, getting
ready to lock in and get a ton of work done. It's just a very
satisfying feeling. And so I wanted to capture that feeling
plus
18:51
just the fact that founders drink a lot of coffee, but also this
idea that the best founders I've talked to take their work very,
very seriously, but they don't take themselves seriously at all.
And I think that's the one commonality between all the best
founders that I've come across. And so the name dumbfound, you
know, it starts with dumb, but it actually means amazed or in awe.
And it's the founders journey.
19:21
Right? You start off dumb because you don't know what you're doing.
Maybe you're taking a huge risk. are, you know, you're starting a
company, you feel dumb a lot. And if you've been a founder, you
know exactly what I'm talking about. But you keep grinding and you
keep working at it. And little by little, it starts to
become a really amazing journey. People looking on the outside,
they're like, wow, how did you, like, how did you start a company?
That's, that's amazing. That's crazy. And even more than
that, you look at your progress.
19:50
Even though some days it feels like you're going backwards, it's
really awe-inspiring. And so that's why I wanted to capture with
Dumpfound. In the name of the company. Bravo. I will have to
order some from you. You know, I use the term
pre-naps. Tell me in your consulting practice now, because
you are working full-time. This is your gig and the
coffee.
20:19
What is it that you found the secret sauce to scaling a co founder
relationship? Right? What is it? What's your secret sauce? Or
what have you observed in high performing co founding teams? Yeah.
Everybody asks me what they can do for their co-foundership
so that it improves their company. That's the wrong question.
That's backwards.
20:49
the best co-founderships I've seen all use the company as a means
to improve their co-foundership. Tell me about that. that one more
time. This is important for my listeners. Yeah. Instead of using
your relationship as a means to improve your company, use your
company as a means to improving your relationship. Okay. And I'll
give you some examples. Back when I was teaching, I would,
you know, make
21:18
groups of students and teams randomly. would draw stuff
out of a hat randomly. And that didn't guarantee friendships.
In fact, a lot of them ended up fighting with each other. And so I
thought, okay, maybe they should pick their own teams. And
that didn't guarantee friendships either. In fact, some of them
ended up fighting even harder than randomly assigned teams.
And then I thought,
21:47
Why is that? How can we create teams where everybody gets a pretty
good experience out of the class? Because we all know group
projects, our group projects, and there's always somebody who
either pulls the team forward or drags it behind. And
so I was looking at the best performing teams, the ones that blow
my mind. And I found that all of them, regardless of whether they
were friends before the class or they had met for the first time
during the class,
22:18
they all saw the class, the course as an opportunity to hang
out and have fun, joke around with each other, but also do
something very interesting like building a company. And so that was
always in the back of my head. And then when I talked to
co-founders, I've talked to over, I believe like 300 co-founders
already this year. The best ones, doesn't matter if they were
friends before they started a company, but they use the company
as a means.
22:46
to improve their friendship. So what does that look like? Well,
it's easy for co-founders to silo and say, okay, you do the
engineering, I do the marketing, and we come together and share
progress. That works for clarity, but not so much for
compatibility. The best co-founders kind of do everything together.
Even if they're, you know, one person is not technical, they're
still very involved in the product with...
23:13
talking to users or creating documentation or making
wireframes or mock-ups. And for the non-technical co-founder,
they're also very involved in the marketing and the sales and the
pitching because a lot of people think, oh, it's not my strength.
So I'm not gonna be involved in it. You're the expert on it. I'll
let you handle it. But if you think about friendships, that's not
really how we operate, is it? You don't divide responsibility
so rigidly with your friends.
23:42
You do everything together because it's fun. Share
responsibilities. Maybe somebody is better at it. Sure. But that's,
that's part of the fun. And so when I realized that, and I, I
communicated it to people who were asking me how to do the
opposite, do it the wrong way. When I told them what I thought was
the right way, all of them had a light bulb moment go off in their
head.
24:10
And I would ask you how does friendship scale? If I'm going to
pressure test your your your the, the, guess the empirical
data, right? You've taught many, many classes,
you've worked with co founders, you've worked with co founding
teams, let's say. How do you scale that?
24:40
If you can imagine like a staircase model at each step of a
co-foundership, there are different levels of sacrifices that you
have to make. So for example, when you choose co-founders, you
sacrifice the ability to become co-founders with anybody else. And
then you start working on your product and you sacrifice maybe some
nights and weekends. Maybe you're sacrificing some Netflix
time.
25:09
And then you go up a step, maybe your company has some traction and
you've got some users and you sacrifice having a day job or
having a stable income, or maybe you sacrifice some sleep some
nights. And so the sacrifices become more demanding. And if you
translate that to a friendship, it's kind of the same. you become
friends with someone, you're not necessarily eliminating all
other friendships.
25:36
but you are eliminating some options for how you spend your time.
Now let's say you have families or you move to
different cities depending on your stage of life. The sacrifice is
the effort that you need to stay in touch. Now, how many friends
have we had in high school that we don't talk to anymore
because we just never stayed in touch because we didn't make
that sacrifice. And so back to the co-foundership, a lot of
times the company might be progressing.
26:05
You have your product and then some users and then some funding and
then some more users. one co-founder decides that the next
level of sacrifice is not worth it. Maybe they cannot quit their
day job. Maybe they have kids that they have to spend time with and
want to spend time with. they have, you know, whatever the
situation is, it might not be malicious. It might just be
circumstantial, but for one reason or another.
26:32
they decide that the sacrifice to move to the next level is not
worth it anymore. But that usually doesn't mean that they quit.
That usually means that they stay at their current level of
sacrifice and they keep doing that. And so the other co-founder or
the other people are continuing to do that. And that's a case
where it doesn't scale. And so to be able to scale, I'm not
saying you have to sell your house and free a personal runway
or never spend time with their kids.
27:01
The important thing is to understand where each co-founder is on
which step and where the company is at which step and to
recognize what are the milestones and the sort of
achievements and the effort needed to unlock the next step. And so
when you're very clear about that, it becomes very simple
and apparent what you need to scale the co-founder show.
Excellent.
27:30
And I'm certain that not not all relationships have happy
endings. And that's when we get to splitting the equity,
right. And hopefully, with your advice, there were
there's been, you know, a stakeholder agreement, a priori, and
there's cordial negotiations. And that's for another episode.
So Tim, how
27:58
Can my listeners contact you? I'm pretty active on LinkedIn.
You can find me by searching my name, Tim He. Yes.
I also have the newsletter, the Cherry Tree newsletter.
I read every reply to that myself. And it's really fun
to see what people are saying. So if you want to email me or reach
out on LinkedIn, I'm available on both. So that's Cherry
Tree. And the coffee.
28:27
coffee company? What is it again? It's dumbfoundcoffee.com.
Excellent. Excellent. Is it dark roast or you do that? Do you have
several roasts? It's a so it's a medium roast from Costa Rica.
Costa Rica. It's delicious. I've tested over a dozen
different coffees for this. My girlfriend and I we were way over
caffeinated many days to find perfect bean and I think we
did.
28:55
All right. I'm more of Guatemala and darkerist than we have,
but willing to try. Thank you. Thank you. You know, I do like
to bring all my guests back to the sandbox to touch on
the three cornerstones of the work that I do, which is
around resilience, purpose driven, and scalable growth, and
ask each of you to describe
29:25
what does the meaning what is the meaning of that word for
you? And here's to you, Tim, what does resilience mean
to you? That's a good question. I've been thinking about that a lot
lately. And by default, you know, we all think of the
get knocked down seven times, give back up eight, or
keep going when it's hard. And those are really inspirational
when you feel like being inspired.
29:54
but on the days that you don't feel like you're being inspired, on
the days that you're knocked down and everything sucks, I think it
can be frustrating to hear stuff like that, you know, because
you're like, just go away, give me a minute and just leave me
alone. And I think that's also a sign of resilience,
just taking the time and the space you need. You don't need to be
motivated every day. You don't need to grind every day, despite
what startup culture tells you.
30:22
sometimes being resilient is just recharging. And I've been
doing a lot of that lately myself, and it's been helping me stay on
this path.
30:32
I'm an entrepreneur and working with entrepreneurs. I like it
recharging. How about purpose driven enterprise? Yeah, very
purposeful. I'm a bit unconventional, but purpose. I, I like this
company, my company, because you're right, I am purposeful.
There's, there's a magic that happens when I do my job, right? And
co-founders have the relationship that they want.
31:02
and the company that they want to build. And I think if you do your
job right, and you're genuinely happy because of a magical feeling,
and I use the word magic because there's really no way to describe
it. It's not the pay, it's not the hours, it's not the
freedom, it's not any of that. It's a magical feeling. And if you
have that, I think the purpose is good. And no
other...
31:31
purpose-driven company that I've talked to denies the magic
that happens when they do their work, right? I often,
you describe it as magic, right? It's the flow, you're
working with your clients and just seeing that your inputs
valued, right? I call that joy, right? So when you
discover or feel joyful,
31:59
in what you're doing with your clients that is resonated and
purpose. Thank you. That's an amazing description of magic.
What about scalable? The title of this episode that we
chose together once I understood your practice is scaling your
co-founder relationship. So what does scaling mean to you?
32:30
I mean, change is inevitable and scaling is just adapting to those
changes. And in the startup world, we think of scale as
growth, as more users, more money, more funding, more profit.
And that is a type of scale when you're getting out
more than you put in and it's leveraged and that's all great
as a technical term. But I think scale doesn't have to be
confined to that. It can be if that's the context in which
32:59
We want to look at it, but scale is just adapting to changes
and hopefully that change is good because you can also scale
down depending on your priorities. know a lot of founders
who'd rather build a million dollar company than a billion dollar
company. They're much happier that way. And so everybody is
obsessed with growth for the sake of growth and scale gets a
bad rep because of that. But if it's just changing and creating the
circumstances that gives you purpose, then
33:28
It's, yeah, it's all good. Fantastic. Very refreshing perspective,
Tim. Thank you. Last question. Did you have fun in the sandbox
today? Yes, I did. Thank you for asking. And that's just
where I find joy. Thank you for spending time here in the
Founder's Sandbox. To my listeners, if you liked this episode with
Tim Heat, sign up for the monthly release.
33:58
of the Founder's Sandbox, where business owners, corporate
directors, professional service providers provide their stories so
that you learn how to build your company with strong governance as
a resilient, scalable, and purpose-driven company to make profits
for good. Signing off for today, thank you for joining us. Thanks,
Tim.