Strategy Session: Advice from Elan Lee and Sarah Robb O’Hagan

Transcript from https://podmenti.com/t/5f3f04d5120cb9c0

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Hi folks, Jeff Berman here. A key part of our mission at Masters of Scale is to democratize education around entrepreneurship. And our live virtual strategy sessions are one way we do that.
Held in partnership with our friends at Capital One Business, these events bring together early stage founders from all walks of life to get real-time advice from experienced leaders in the masters of scale network.
Our latest event was in May with Sarah Rob O'Hagen, who's been a leader at Gatorade, Equinox Fitness, and other household name companies, and Elon Lee.
My old friend.
and a technologist turned founder of the hit game company Exploding Kittens.
We're bringing you their insights today, and we hope you'll register for the next free virtual event at masters of scale.com slash strategy session.
That's masters of scale dot com slash strategy session.
Elan, you have done it all as a founder, and I want it you to share with me.
What have you found to be the most useful skill you had as a founder and a business leader?
The thing that I wanted to say was, I think I'm really good at communicating, but that felt very generic and it felt very bland. And it actually felt like the antithesis of saying I'm good at communicating. So I thought, well
What is it about communication that I think I've been successful at in the past? And I'm gonna tell you a quick little story. I'm the oldest of four kids, and that means that growing up, it was always my job.
To entertain everybody, right? To come up with the games and go out in the backyard and invent stuff and play stuff and basically like keep all my siblings happy. And my siblings range
Like there's a sixteen year age gap between me and my youngest sibling. Yeah. And so we all have different interests and different tension spans and different communication styles. And I realized that
That was like the perfect training for me to learn how to communicate effectively. And in one very particular skill, which is
Providing context. And I think that.
Has
Helped me.
As an entrepreneur, as a CEO, more than almost anything else I can think of.
How many times have you had a conversation with someone and they're talking and you have to ask this very fundamental clarifying question, right? You're like, wait, wait, which project are we talking about? Wait, wait, wait, wait, which meeting was that, right? Like context is missing. And the reason it's missing is because they didn't start at step one. They started at like step four or five. Step one through
Three is in their head, right? And they're just assuming you're caught up with them. Yeah.
I'm really, really, really good at starting at step one.
Really good at that. Yeah. So there you go. There's my story. I would say that
My greatest skills was
Related to communication, but sort of
brand building and getting people really excited by an idea. And hearing you, I'm sitting here going, well, why is that? Because I had to fight to be heard in my family. Right. Right. Oh, I love that.
All right, well, we are going to turn to our very first call up. So I think Nick Mondi, are you out there and can we hear from you?
I am, Sarah Alan, nice to meet you both.
Thanks so much for taking the time.
So I'm the CEO and co-founder of Learn Fresh. We're a nonprofit focused on leveraging the power of sports and entertainment to inspire students' STEM education in K12 learning. So basically what we do is use the thing that kids love already, sports.
touring artists and gaming to get students passionate in their classroom, particularly math around math education, science education. When you think about math, you know, it's a space where students often walk into the classroom and feel like the learning doesn't have context with the world around them. And so what we aim to do is bring the things that kids love from the world into their classroom.
So we've used digital games as well as physical tabletop games to do this. Our flagship programs include initiatives in the NBA, WNBA, MLBPA, and MLS. And we've reached over one point two million students across all fifty states.
Wow.
Did you say one point two million student users? Can we just take a minute?
That's incredible. Thank you. Amazing.
You said it's through videos, like you provide videos the teachers play in their classrooms?
So we actually have games that mimic the real sport of basketball, baseball, use real player identities, player data, and are licensed by the leagues and these games are set up in a classroom almost like fantasy sports league.
So it's never. Thank you.
As someone who works in education, one of the best ways that we can activate that mission is to build
public private partnership where
organizations like ourselves are working with companies to help show students what their skills can do for them in the future. And so we'd love your perspective as people who have worked as leaders in the for profit sector on how we can best position ourselves as nonprofits to support that space and vice versa. Why should companies feel energized around this work?
I do believe when it comes to corporate social responsibility.
Honestly, it's like doing the right thing.
is just critical to running a great business, period, end of sentence.
And when I say doing the right thing, like building
A business that is good for multiple stakeholders, investors, community
employees, et cetera. So I think
To me, it's it's a fundamental sort of plank upon which every business I have built or been involved with runs. And then when you are able to step into those.
partnerships, as you said.
Between private

you're able to come and energize the potential buyer because you you are showing that you're already energizing the community. You wouldn't have one point two million amazing young student users if you weren't already doing these things right, I would imagine.
Nick.
What is the mission statement of your company?
Yeah, so our mission statement is to inspire students STEM education through the power of sports and entertainment and drive rigorous exploration through STEM learning.
Okay.
I love that.
And the follow up for me would be how do you choose your partners?
Yeah, so to your point around the mission, it's definitely mission alignment, right? And so when we're working together to
Think about establishing a a philanthropic relationship.
The kind of shared community focus is something that's deeply important for us. It is quite a process on the nonprofit side to vet and like work through all the different relationships to continue building.
Yeah, absolutely. If you focus on that rigorous criteria and look at the pool of companies available to you.
I think the answer to your question is like
These are the good guys. This is our play space. This is the area that we will participate in. This is the area where our values align. We can make a credible pitch to any of these companies that our goals are aligned with your goals, our responsibilities are aligned with your responsibilities, and we're all going to go forward together. So
I realize it's not like the exact answer that you're looking for, but I do think that it's very valid to say in some senses.
You have such a strong vision and such a strong responsibility here that
You almost don't need to worry about a generic answer for the entirety of the universe. You need to worry about the answer that you've already supplied.
to push your business forward and to find the relevant partners.
Definitely.
I would add to that.
Awesome answer related to the moment we're in now.
Once you've narrowed in that group of potential partners.
Also just be super aware of who's dealing with what in any moment because
Honestly, some businesses are massively stressed out by the tariff situations, others less so, right?
Today.
Now that doesn't mean that
Two years from now that might, you know, one business's headwinds is another's tailwinds.
Yeah. Absolutely resonates. And in this moment, I'm actually at a a conference in the Bay Area right now with a bunch of other nonprofits who are grappling with funding challenges in the sector. And so
that advice of honing in and focusing on
The
closest proximity prospects is really fantastic. Appreciate that.
Wonderful. Yeah.
By the way,'cause everyone is going to have different headwinds at different times'cause
Even think about the pandemic. One minute it was a tailwind for someone and then a headwind. You know, that changes. So don't ever sort of
feel that oh gosh, because it's tough economic times, no one's gonna invest. It's just you have to get even more clear on finding the ones that
for whom you are the best fit in that moment.
Definitely. During the pandemic, we had a uh interesting experience'cause it actually led to a lot of growth for us.
Okay.
And so, you know, they say the only way to it is through it, and we've definitely experienced that before.
Yeah.
And I sometimes think too that in Eli, I'd love to hear your perspective on this, but sometimes
Like a nonprofit by definition in recessionary times, it's going to be tougher.
But it's often when you hone yourself and relationships you win in that moment.
If you can get through that, you will suddenly get so much stronger on the other side because you've had to be so much more focused. I'm I'm sure Ilan, you would have experienced that.
It's so true. I mean, the two examples really are for me at least the pandemic and uh the current tariff situation, where like when the pandemic first hit.
Me and every CEO I spoke to was like, Well
This is it. We're just gonna shut our company. Hopefully it's just for a little while. And it was only once we started focusing on like, wait a second.
If everyone is thinking
Shudder, shudder, shudder. Right. If everybody is thinking we're going to sit still now for a while and like figure out what comes next.
It was only then that we started thinking like
Some games would make that nicer.
Maybe we can use this as an opportunity. And it's the same thing now where tariffs, you know, it's a roller coaster. We have these war room meetings at my company every single day about tariffs. And we come up with a plan, and then the next day the policies change and all of our plans disappear and we got to do it again. It really tests your patience.
But at the same time
It's brought us way closer to a lot of other publishers who are going through the exact same problems and banding together, trying to find creative solutions, trying to say we're stronger if there's more of us, if there's more inventory we can talk about, if there's more leverage we have in these negotiations. And we never would have come together had it not been
for this very frustrating tariff situation. So there's always that silver lining
Being aware of everybody else's
context their situation
will let you figure out how to talk to them and how to find paths forward together.
Still ahead more insights from Sarah RoboHygon and Ilan Lee.
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Welcome back to Masters of Scale.
Next up, Sarah Nylon, get this question from the founder behind a small business in Los Angeles.

Mm-hmm.
Hi Sarah and Alan. My name is Arielle Alunga, and I'm the founder and CEO of Carlos Fresh Market, located in Los Angeles, California.
In 2023, we opened Carla's in the Highland Park neighborhood of LA, with a mission to bring farm fresh produce, quality pantry goods, to a vibrant and diverse community.
The past two years have been a journey.
With plenty of ups and downs.
But I'm committed to creating a space where people can discover delicious food in a warm environment and a business model that fairly compensates local suppliers.
We're reimagining the neighborhood grocery store.
Carlos is bright and colorful and open.
Grocer shopping should be fun.
But I can't do it alone.
My question has to do with building a great team.
As a solo entrepreneur, my instinct is to take on all the challenges by myself.
How do I know when it's the right time to delegate?
How do I find people that are as passionate about my business as I am and want to help me scale? Thanks so much. And if you're ever in LA, stop by Carlos for a visit.

Well
Love it. I love it.
Yes.
So the question is
Essentially.
How do I not do everything myself? And I'm gonna summarize it all the way down to that because I'm part of so many different entrepreneurial groups, right? And and they're basically like.
therapy sessions, right? We all sit down and we have coffee and we talk about like
How hard this job is. And
The topic that has come up
at least once a month for maybe 10 years of doing this is how do I not do everything myself? When is the right time to delegate? How do I find the right people? How do I explain it to them? How do I deal with them not doing and not doing as well at it as as I know I could do and how do I trust the process on and on and on, but it all comes down to how do I not do everything myself?
And
I'm gonna share just one
quick story that has really guided my thinking on this.
hasn't solved it. I still really, really struggle with this, but I used to be the chief design officer at the Xbox for a long time. We made all these games and all this hardware. And my mentor there was the smartest guy I know. His name is Jordan Weissman.
And he is a legend, legend, legend, legend in the video game industry. And he taught me basically everything I know. And
I was struggling with exactly this. We were working on this massive project. It had like hundreds of people, each working on their own individual parts, but I was the lead on the project and I started it. And so the first
Two months of the project was literally me just doing
Everything writing all the code, doing all the art, writing the schedule and handling the budget and just everything. And I installed a little bed in my office and I would sleep there at night because why bother to go home? I'm just gonna have to be here in two hours, right? Like it was not a good way to live, but
You know, when you're in your twenties, that seems like a reasonable approach to a very difficult problem. Okay. So
I eventually started to burn out and the quality of work went way down.
And Jordan came to me and he said, You have to start delegating. You have this whole team, and they're literally sitting around waiting for you to tell them something completely underused. And I said, Okay, you know, you're totally right. I can't maintain this anymore.
And I picked one guy and I gave him a job and he completely screwed it up.
Like completely. And I was like, Well, there we go. I'm just gonna I'm installing the bed again because I'm never going home.
And
Jordan sat down with me and he said, Okay, you said he totally screwed that up.
Let's sit down and actually look at the output of his work.
And we looked at and I won't get into the details, but like
What I was describing as a screw up, he was able to recontextualize and describe as a success.
And he said.
You think different work is equivalent to bad work. That's your problem, right? If you can just get it in your head.
that just because someone solved a problem a different way than than you would have and produced a different set of output than you would have.
That doesn't mean it's bad. It just means it's different.

And still.
It's long winded story, I apologize, but the answer I think

Is the right time to delegate.
I believe the answer is
Whenever you can get it in your head.
That
Different work.
Does not mean
Bad work.
And as soon as you can
say like I'm okay with that. I'm ready for that.
That's when you go and you hire someone. That's when you give them responsibilities. That's when you mentor them. That's when you do all the all the smart stuff, right? Define their goals, tell them what the box is that they're working in, define success, all of that.
And then their output is not going to be what you expected.
And that
Is not bad.
I love that story because boy, I I feel like I have lived the exact same story in my career. I remember mentor
Once saying to me, individual heroics will not get this job done.
And it stayed with you.
And that'cause that's what you were doing. Like
Sleeping in the office, like
That is not scalable.
That said, I do understand for particularly this kind of business that we're talking about.
With RL.
It's hard to really hire these kinds of workers and be completely sure they're gonna stay with you because they might turn over. I would take a step back and say
The first thing is make sure you spend tons of time in the upfront really talking to the co worker that you're hiring.
Are they as passionate about this business as you're gonna need them to? And they bring that different
Work.
If you know that they're coming from the right place and they're caring as much as you
You're actually going to be more willing to hear it than if you think they're just someone who's mailing it in. And so I think there's something to be said for
Who you bring on in the first place.
And then the other thing I'm curious if you've has this this experience, but I do remember
early in my career really struggling with the delegation thing. I think we were the same as everybody does. Everyone does.
And then at some point
Learning
When you truly empower someone, you'll be shocked. They might actually come back and do a great job. You might be pleasantly surprised.
It's so true. It doesn't happen that often that I'm I'm like, wow, that's better than I could have done. But when it happens, it's like
Hold on to that person'cause whoa.
I had this working at Microsoft and I had an administrative assistant, this woman named Carly McGuinness, and
She was very smart, amazing at her job. And we were at this point.
where there was some project that was just going completely off the rails and I was understaffed and I didn't know what to do. And she was watching me just like sit in my office until you know one and two in the morning. And uh one day she came in and she's like
I just want to help. Like
I'm not trained at any of this.
But I'm a really fast learner.
And can I please, please, please help?
And I gave her the task.
And she
Absolutely knocked it out of the park. And I'm gonna jump right to the end of the story, which is Carly McGinnis is now the president of Exploding Kittens.

Best All right, I think we're going to our third caller now.
Thank you for having me. I'm excited to be here and get your advice on what we're doing. So I'm Dana Griffin. I'm the co founder and CEO of Eldera.
Eldera is a technology platform that connects generations and brings generation together in a way that's good for young, good for old.
And for society.
We bridge
young people with older adults in a way that solves for loneliness in older adults and mental health in kids in virtual conversations.
I started the company in twenty twenty, and we initially focused only on intergenerational mentorship.
And that worked really well because we're tapping into a human resource that's underutilised.
Then our mission evolved and we realized, wow, there's so much more we can do with older adults. So now we evolved into a platform where older adults can come and contribute their wisdom to society in a way that makes an impact and leaves a legacy. People love our product and we've
been in the media and in the press and we've had so much exposure that now
We are incredibly fortunate to have all this inbound.
from people and organizations that want to partner with us and want to build a into their ecosystems. And we're so excited and grateful for this, but
My question is as we're navigating this inbound
How do we protect the soul?
Of the product that people really love, that true one on one deep human connection.
While also taking advantage of the growth opportunities in education and healthcare in corporate.
So how do we
decide what do we say yes to, what do we say no to, and while focusing on the long term success and impact of our company.
I am imagining your amazing business.
twenty years from now it's gonna be like massively world dominating.
But one of my challenges in my career, I led the turnaround of the global business gator, the five billion dollar global business.
The reason it was needing to be turned around was because
They had gone so far away from what their core mission was, instead of like selling
Really great products to athletes. It was like, let's just sell it to anyone who needs a hangover cure or just sitting on a couch and
Suddenly this really big business stops growing, right? Because
It's lost touch of its core, and suddenly.
Competitors come into that core space because they can be more authentic than you. So
I am very passionate about this question, Donna, because I think your
super wise to be actually thinking about this early on and
I think I have seen so many entrepreneurs who get a little bit too excited by the shiny object or the big
opportunity that takes them
To grow faster and
I actually think the answer to question
kind of goes back to what we said to Nick earlier, which is let's start with the mission of
Your
Amazing platform and let's make sure that you are so true. Every decision are you being true to
the mission. So maybe you can
Articulate like Nick did, what is the mission of the platform and
Even if you're scaling faster.
Are you still staying true to that mission?
And then the last thing I would say is are you
Staying within your core, because a great line that I had said to me once, and I've kept it for my whole career.
Is
Your adjacency, so the adjacency to your core business is somebody else's core.
Which means they're gonna compete even faster and heavier and et cetera.
You've created something unique and brilliant and hasn't been done before that is your core.
Are these opportunities outside of that, or are they still in the core? That would be my question for you.
Donna.
Thank you. That's that's a great question. Our mission is to unlock the time and wisdom of older adults as a new natural resource for society.
That's how we think of it. And our first application was to connect
older adults with young people in a way that solves one of the biggest healthcare challenges globally, which is the mental health of young people.
Now
There are so many other things that older adults are fantastic at. And I think that's where the question comes up and where we're getting pulled.
Can older adults help?
Other adults.
Yes, they can. But where do we stop?
Right. It's easy to say no when they're not values aligned and they don't drive the business results. Right. An easy no. But you know what?
Sometimes
Not easy, even when they intersect and they check both boxes, it's not necessarily easy.
To say yes to that opportunity.
Like what are the criteria to say yes to an opportunity? Okay.
I have no idea. But
Yeah.
Because I'm I'm not very good at telling you
why to say yes. I think that's a very personal thing. And I think you really have to internalize your own mission statement, your own values. I cannot tell you how to say yes. You know what I can do? I can tell you how and why to say no.
And maybe that'll in a roundabout way get you to the same place. So made a little list. I'm gonna read this list off. Here we go. So
As you look at opportunities, here are, in my experience, the main reasons to say no.
An easy one is is there any risk in association with this brand, with this partnership, with whatever it is?
If so, run for the hill. Is it a distraction either to your mission or to your values? And that's really pokes at misalignment. Like
Something could be really, really interesting, but you've got this little voice in your head that will answer that question very clearly, and you just got to train yourself to listen to that little voice.
The next one I have is overextension. And this is something that you see just
Obliterate new companies. And you have to be very, very careful. You know what you're capable of, you know what you can just stretch to.
Do not go beyond that because the risk that you will take on in trying to build up the facilities to go beyond your limitations, to extend beyond what you're capable of, will I promise you sink your company.
Plus one on that. Yeah. And it's just from experience, right? Like I've been there. I've done that. I've got the ruins of a company to show for it.
An easy one is lack of resources. And this really ties into overextension, but the lack of resources is like very physical, right? Like how many people do you have? What does your bank account look like? What does your financial structure look like? What does your cap table look like? What does your loan structure look like? Like just
Really
as realistic as possible about what you have and what each partnership is going to take away from that.
And then see what you have left. And when you're in the red,
You've made a mistake.
And then the final one is just
The ick factor. There is that little voice in your head where when you say, Should we do this, should we do this, should we do this?
Sometimes that little voice just says, oh, this just feels bad. No. Right.
Don't dismiss that as trivial. That is a very important part of your brain telling you a very important thing that it cannot articulate. It does not have the vocabulary to tell you why.
And you should pay attention to that as well.
I love the point about don't
distract and overextend because I'm with you I've seen that.
kill companies so many times. And I also think
Donna, you are onto something special here. You know it. You just said people love your product, right?
And
Seems to me sometimes you're under a lot of pressure, whether it's from investors or whoever, to grow
Crazy fast.
Whereas I think about new businesses a little bit like planting a tree. The deeper the roots are.
the stronger and further up the tree is going to go. And so if you haven't
Built deep enough roots in this first
section of
The adults to the kids.
To be ready to go to the next, whatever your next line is.
That's when you start to like the tree gets heavy and starts wave because it hasn't yet got enough deep roots in one way.
And so I I love that analogy because
I think the number of times I've seen found is like
company I was lucky enough to be involved with was Strava, you know, the running app and
That is a business that, believe it or not, has never ever spent money on paid marketing to get people to come because it was so beloved.
And they went slowly and surely and now obviously it's just ginormous. So
If you're feeling pressure to jump at something, I love the point about the ick. If you're feeling
Pressure to go ecky.
Don't do it because
You have something special and it will stay if you nurture it would be my
General sense.
So, so so smart. I want to add
Just one more thing.
There's something I do. I've never said this to anyone before, but there's a little tool that I have that might help with this process. I have a dummy email account. It's a generic Gmail account that I created and
Um
All I do when I have a proposal, like someone that wants to partner with me, after I've gone through all the contemplation, yes, no, and and I'm still on the fence. I still don't know. Both lists, pro and con, are exactly the same. I have no idea what to do. I write out an email to them.
Saying, Let's do it.
Here's why I'm excited. Here's all the wonderful, amazing things we're gonna do together. Here's the deal structure I propose. Here's everything. It's a very long email. And I send it to that dummy account.
And then
I go and I sit down with my wife and I say, I just signed a deal with
Facts.
It's done. I just sent the mail. It's done.
Here's what we're doing.
And between her reaction
And all those little voices in my head reacting to the mail that I literally hit send and it's gone.
Then in the m by the morning
I'm either
Terrified or elated?
And now I know what to do.
That's a great strategy. It feels like both of us
Yeah.
Pushing me towards following our instincts that got us to where we are now and just really listening.
Yeah, good luck. You're in such a great position.
For sure.
Such incredible advice from Sarah and Elan and that conversation. Special thanks to them for their wisdom and all the business owners who participated in our event.
I'm Jeff Berman.
Thank you for listening.
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