Intro

Jonathan Lowenhar, a seasoned entrepreneur and CEO advisor, shares his insights on the journey of founders transitioning into effective CEOs. With nearly 30 years of experience, he has successfully navigated various roles in startups and large companies, ultimately leading him to create Enjoy the Work, a firm dedicated to helping founders develop their leadership skills. Throughout the conversation, Jonathan emphasizes the unique challenges faced by startup CEOs, particularly the lack of formal training and the overwhelming pressure to succeed. He reflects on his own path, highlighting the importance of grit and resilience, shaped significantly by the influences of his family. The episode offers valuable lessons for aspiring entrepreneurs and those interested in understanding the dynamics of startup leadership.

Bio

Throughout his nearly 30-year career, Jonathan Lowenhar successfully built a $1B business segment for a large public company, guided the turnaround of a distressed $100M+ revenue business, launched and sold a venture-backed startup, and led another startup that eventually was acquired for just under $1B.

Those very different endeavors led Jonathan to obsess over a single question, "how does a founder become a great CEO?" He interviewed hundreds of founders and investors seeking clarity to that question. And when no good answer presented itself, he teamed up with a group of exceptional former founders, operators, and investors to create their own solution.

Since 2015, Jonathan has led Enjoy The Work, a firm with the singular mission of helping founders become great CEOs. Founders invent miraculous things. Enjoy The Work’s role is to teach founders how to build high-performing companies to bring those inventions to the world.

Episode

In this episode, Jothy Rosenberg engages in a compelling conversation with Jonathan Lowenhar, a seasoned entrepreneur and leader who has crafted a remarkable journey through the startup landscape. With a professional history that spans nearly three decades, Lowenhardt has successfully built and sold several ventures, including a company acquired for nearly $1 billion. The episode delves into his early career in the casino industry, where he honed his skills in marketing and operations, and how those experiences shaped his perspective as a founder. Lowenhardt's transition into the tech world began in earnest when he relocated to California in 2007, a move spurred by both personal and professional aspirations. The discussion reveals his initial struggles to navigate the unfamiliar territory of startups and technology, a journey that ultimately led him to create Enjoy the Work, a firm dedicated to helping founders evolve into great CEOs.

Throughout the episode, Lowenhar emphasizes the importance of mentorship and the need for structured guidance in the chaotic startup environment. He articulates the challenges faced by founders, often feeling isolated and underprepared for the weighty responsibilities of leadership. By sharing insights from his own interviews with hundreds of founders and investors, he highlights the common hurdles they encounter and the universal questions they grapple with. The conversation paints a vivid picture of the emotional and practical complexities of startup life, underscoring the value of community and support in overcoming these challenges. Lowenhar's commitment to fostering a culture of learning and resilience among entrepreneurs stands out as a central theme.

Listeners are also treated to personal anecdotes that enrich the narrative, such as Lowenhar's reflections on his family, his upbringing, and the grit he developed through adversity. He recounts the lessons learned from his father, whose own challenges instilled a strong work ethic and determination. As he relates his entrepreneurial journey, it becomes evident that personal experiences and professional endeavors are deeply intertwined, shaping not only his career trajectory but also his approach to teaching and enabling others in the startup ecosystem. The episode encapsulates a profound message about the power of resilience, the necessity of mentorship, and the joy of supporting others on their paths to success, making it a must-listen for aspiring entrepreneurs and seasoned leaders alike.

Takeaways

• Jonathan Lowenhar's journey from casino industry to tech startups highlights the importance of adaptability.
• Founders often feel isolated, needing support to navigate the challenges of becoming CEOs.
• Enjoy the Work aims to teach founders how to build high-performing companies effectively.
• Grit is developed through overcoming challenges, as shown by Jonathan's personal experiences.
• Learning from trial and error in startups emphasizes the need for guidance and mentorship.
• The shift to remote work has changed how startups can operate and find support globally.

Links

Jonathan's Enjoy the Work: https://enjoythework.com

Please leave us a review: https://podchaser.com/DesigningSuccessfulStartups

Tech Startup Toolkit (book): https://www.amazon.com/Tech-Startup-Toolkit-launch-strong/dp/1633438422/

Site with all podcasts: https://jothyrosenberg.com/podcast

Jothy’s non-profit: https://whosaysicant.org

Jothy’s TEDx talk: https://www.youtube.com/watch?v=PNtOawXAx5A

Chapters

• 00:03 - Introduction to Jonathan Lowenhar
• 00:09 - Jonathan's Journey into Startups
• 00:45 - Career Highlights and Achievements
• 01:10 - The Question that Sparked a Mission
• 01:27 - Founders and the CEO Transition
• 01:49 - The Origins of Enjoy the Work
• 02:14 - Personal Reflections on Entrepreneurship
• 02:15 - Building a Startup Advisory Business
• 02:42 - Navigating the Challenges of Startups
• 32:21 - The Importance of Grit in Entrepreneurship

Hello, I'm Jati Rosenberg, the host of designing successful startups, where today's guest is.

Jonathan Lowenhardt, my future ex wife who I give so much credit to, introducing me to this crazy world of startup life.

I moved here not really knowing what I would do next.

So I spent, I don't know, eight months, ten months, a little bit lost in the desert, trying to get a sense of what it meant to be in these strange technology circles where at the time, I'm not sure I could have spelled the word technology.

Throughout his nearly 30 year career, Jonathan Lowenhar successfully built a $1 billion business segment for a large public company, guided the turnaround of a distressed $100 million revenue business, launched and sold a venture backed startup, and led another startup that eventually was acquired for just under 1 billion.

Those very different endeavors led Jonathan to obsess over a single question.

How does a founder become a great CEO?

He interviewed hundreds of founders and investors seeking clarity to that question, and when no good answer presented itself, he teamed up with a group of exceptional former founders, operators, and investors to create their own solution.

Founders invent miraculous things.

Enjoy the work's role as to teach founders how to build high performing companies to bring those inventions to the world.

And here is Jonathan.

Well, hello, Jonathan.

Charlie, it is a pleasure.

How are you today?

I am good and I am enjoying fall.

I am jealous.

It feels like some of us locally have been judged by the Almighty and we have descended into the pits of hell.

Oh, good, good, good.

Okay, wherever I.

Where are you originally from and where do you call home right now?

I'll answer reverse order.

So I live just south of San Francisco.

My wife and I are a little girl and our dog, but I'm a Jersey kid originally, so my parents are both Bronx.

And then when they decided to have a family, they moved to South Jersey, had my sister and myself.

I'm a few years older than her.

I grew up Jersey, then undergrad in upstate New York before I started to move west.

That took me to Las Vegas for about a dozen years before I got to the Bay Area.

My memory is escaping me.

2007 is when I got here.

You know, I lived in sort of the Bayern except on the other side of the hills.

I lived in Santa Cruz for ten years.

I'm jealous.

I think you made a better choice in pre Covid times.

I really enjoyed the access to the city and my wife and I love living in an area where everything was highly walkable.

We weren't working from home then.

We were walking to offices and walking to clients and taking advantage of all the fun things the city had to offer.

Now I'm home much more.

Santa Cruz would be an appealing diversion.

What had you leave first?

I got to say, though, that we.

I was commuting and I was commuting over Highway 17 twice a day.

Yeah, you're a braver man than I.

That was very dicey at times.

I specifically brought a BMW convertible because I felt like it would be better on that road than anything else I had ever driven.

And I was right.

It was great.

But so many times a day that road just gets locked solid because, you know, one mistake and.

And then the road is backed up for 10 miles.

Well, I think you made the right choice that if you had to suffer that commute, at least do it in a toy.

The way we got moved to the east was that after I did my first startup, which was in Sunnyvale, and then before I, I did another one, I took a little stint working at Borlande.

Now, what was great about Borland was, well, there were many things, but I didn't have to go to Highway 17 anymore because they were on the same side of the mountains as me.

So it was a very, very short commute.

But Borland did an acquisition of a small startup in the part of Boston called Alston.

We were not good at acquisitions.

We'd really screwed up several.

And I felt like this one was so important to my division that I couldn't afford it to get screwed up.

More direct oversight was required that brought you back east.

So I'd moved the whole family to the.

To Boston for a year, ostensibly a year.

I'm still here 27 years later.

Yeah, it's a long year.

Yeah.

And my kids were in junior high, so they really hated me for doing it.

But shortly after we moved, the Red Sox started winning, the Patriots started winning, and we went on a tear where.

All four teams, just to be clear, are you taking credit for the end of Boston's curse and their ascension to sports stardom over the last 20 years?

It's like you were the reason, because that's pretty amazing.

Well, I want to spread the credit to my whole family.

That's fair.

Okay.

Okay.

I don't think you're getting proper credit.

I think this should have been newsworthy.

Boston was a fun place to be a sports fan for a long time.

I am a struggling New York sports fan, particularly the New York Giants, which goes back in my family a bunch of generations, which for most of my childhood was joyous until frankly, the last 13 years has been just one misery after another.

There are more long suffering sports areas than mine.

I can't fully complain.

But as at least as a Giants fan, it has been a painful journey.

So speaking of journeys, tell me about your entrepreneurial journey.

Cause you kind of had an interesting set of twisty little paths.

I certainly find it interesting.

I think we're all the hero of our own journeys.

I'm on kind of the third career, so career number one is I worked in the casino industry.

I spent my summers of my undergraduate years interning in casinos in Atlantic City, in Las Vegas.

I moved to Las Vegas the moment I graduated and I spent the next dozen years with every intention of move up the ladder in functional roles until someone gives me the opportunity to run some of these businesses myself and then eventually maybe I'll be able to be a part owner.

That was the path I dreamed.

And I did that.

I did that for a long time.

I was in marketing roles and sales roles and operations roles until I was leading a business segment for a large public company that was about a billion dollars of revenue.

I was on the path.

And while on that path, what I realized was I didn't like most of my life.

I just enjoyed what I was doing professionally and wonderfully.

Coincidentally, I moved to Las Vegas and then my parents ended up moving there and my sister ended up moving there and creating a life for herself there.

Married and had children and so I had roots in Las Vegas, but I by and large, wasn't very happy.

And I attributed a bunch of that to just kind of what life was like there.

As I was maturing in my early thirties and I had an opportunity through business school, which a joint program between Columbia and Berkeley to get exposure to the Bay Area for the first time.

And so I fell in love both with my future ex wife who I give so much credit to, introducing me to this crazy world of startup life.

And I fell in love with this region of the country.

I moved here not really knowing what I would do next.

So I spent, I don't know, eight months, ten months, a little bit lost in the desert, trying to get a sense of what it meant to be in these strange technology circles where at the time, I'm not sure I could have spelled the word technology.

I started interviewing for gigs, VP of marketing, CMO gigs, data analyst, customer intelligence gigs.

And I kept getting to the last stage of an interview cycle like it would be me.

And another finalist for pick your role at a mid to growth stage startup.

And without fail, what would happen is the hiring manager, the CEO, the board member, whoever would say the following phrase to me, your skills are definitely transferable, your experience is really interesting.

And I had this other candidate who's done exactly this job already.

So we're going to go with her.

We're going to go with him.

That happened enough times where I decided if I'm going to live in the home of startups, I need a bridge, I need some career bridge.

And me landing a functional role doesn't seem to be working, so maybe I should just do a startup.

So I started dating all sorts of companies.

I called this my professionally promiscuous period.

And one of the companies I started to spend a bunch of time with was as young as they get.

It was two people with a little bit of seed capital, a prototype that didn't quite work, but a real ambition that was at the intersection of travel, hospitality and analytics.

And I just liked the co founders a lot.

A man to woman, Daniel and Stephanie.

They were good humans, and I could see a bunch of ways I could help them.

So I joined as a board member first, which sounded lofty at the time, but when you realize it's a company with no customers, no real product, and no revenue, being a board member isn't that much, but it allowed me to get to know them.

And I then vetted the idea with my ascending but very small network in the Bay Area of like, is this a startup that has some legs?

I didn't know how to evaluate at the time.

This was nearly 18 years ago, and I got enough positive feedback to say there's something here that, like, I jumped in.

So I ended up joining this young company as co founder CEO with the point of view that this would be my career bridge.

If this company could be viable in some way, I would no longer be Jeffy, honestly, I would no longer be weird casino guy.

I'd be someone who knew how to run different kinds of businesses, whether it was in a big public company, in a GM role, whether it was running a holding company for private equity owner, were now a startup.

Like if I could cover all those branches, great.

And that worked.

So for the next four years, we built a startup that had real customers like Marriott and Wyndham and Starwood, a product that worked, a small team, we raised a couple of rounds of venture capital and we ended up selling the business four years later.

I am not exaggerating when I tell you that I made no money from that sale.

But now I had helped sell a venture backed startup and my reputation was irrevocably different.

And so as I left that business, my first marriage, sadly was coming to an end.

My wife was not healthy, we were not healthy.

That was coming to an end for all sorts of reasons.

And despite the fact that I was now in my mid thirties and I had made a lot of money in my life, I didn't have any money.

So I'm like, I need to get back to work.

This started well because you'd worked at.

The casinos and you'd gambled it.

All, right, that would have been true at age 23.

I did grow up, so it wasn't always true for a lot of reasons.

I needed to make money and so I jumped right back in.

So I spent three months after I sold that first business of like I need to figure out what's next.

And what was wonderfully positive and also shocking is I had all sorts of opportunities in front of me immediately.

Like my brand was just different.

And I ended up joining another young fintech business that was in a category I knew nothing about.

But I knew the CEO well.

He and I had a lot of mutual respect and it's a business where the product worked.

They had first customers and there was just nothing repeatable about the organization.

Yet they didn't have a repeatable way to attract a customer, win a customer, deploy a customer, bring on people into the business, grow the operation.

Those were all things I was good at.

The technology was already solved for.

I ended up joining first as an advisor so I could evaluate the company.

And then I joined as coo and president and I helped grow that business to its 1st $20 million in revenue.

We raised during that time almost $100 million in capital.

That business did really, really well.

I left the business as it got to scale and a handful of years later it ended up getting acquired by SAP for just under a billion dollars.

So my life really changed because of a few different professionally, a few different really important inflection points for me.

When I left that last business, I was now firmly in entrepreneurship.

I had done two startups.

Both were seen as a success.

The first one, you have to squint to say it was a success, but it was a success viewed by many.

The second one was undeniably a success.

Then something kind of sparked an idea in you that made you create the company that you're running now that you've been running for a while.

Yes.

A few forces in my life converged.

One was personal.

I'm single.

And I have the benefit, the privilege, frankly, of saying, like, what do I want the next chapter of my career to look like?

And so I took three months where I told my loved ones of every type, I will take no professional meetings of any kind for the next few months.

I am going to travel and cook and see friends and exercise and read and get clear on what are the ingredients for what will be professional utopia for me next.

And I came out of that with a list, and that list was, and they're going to sound so terribly selfish.

I want a total curation power.

No one will ever again tell me who I have to work with, when or where.

Two, I still want to play with startups.

I love the dynamism.

I love the passion founders have.

I love their tenacity and grit and courage.

Three, I still wanted to teach.

I wanted to teach in some way.

Both my parents are teachers.

My father was a college professor.

My mother taught the gifted and talented program for a couple of decades, both in New Jersey and then in Las Vegas.

And there's something about that that I love.

I've been a guest lecturer many, many, many times.

I wanted some recurring income, but I also wanted to be paid for the impact I could have in a business.

I had all of this criteria, and as my father jokingly referred to me when I shared this with him many years ago, he's like, that's not a job.

And I said, I know, I accept that it's not a job, but now I'm going to go have conversations in the market, and I'm not going to discount this list until I've tested it in the market.

That was one of my forces.

I had this second force in my life that when I reflected on the very, very different companies that I had helped, giant public company division, private equity, few thousand employees, startup from the babiest of stages and startup that was moving into growth stage.

What I recognized is when they all got to a place of rhythm where they were all well run.

And I am blessed to say that all four got there, that all of them, they were well run in the same ways.

The epiphany was all well run companies look the same, and I don't care what they do.

Third force and final one.

The third one was, I start taking meetings.

He has a family office.

He's the chairman of the board for an interesting financial tech business out of Detroit.

He says, I want you to meet a friend of mine who's the CEO I've invested in.

Sure.

I said, I'm unemployed.

Those meetings are easy.

And me and the CEO, he have a conversation, and he's delightful.

He's one of these charismatic, impulsive types.

He fires questions at me.

Delightful hour on the phone.

He said, we need to have dinner.

I remind him, I'm unemployed.

Dinner's easy, my schedule's open, and he very quickly thereafter gets on a plane, comes to the Bay Area, we have a wonderful meal together.

Little French restaurant in Glen park in San Francisco.

At the end of the meal, he says to me, I will move to the board.

You come be president of this business.

Eventually I'll move you to CEO.

You're the right person for this.

And I said to him, I'm enormously flattered, and you're insane.

We've known each other for an hour and a half.

I said, I believe in dating before marriage.

To which he quickly quips, I am indian.

I believe in marriage before dating.

I couldn't compete with that.

So instead my response was, look, here's my criteria.

And I walked him through the same list I had just shared with you.

And he thought about it for a beat, and he just said to me, childly, can we just get on the phone once a week?

You've already done what I'm trying to do.

And I looked at my list, and I'm like, that all fits.

So I said, sure, let's get on the phone once a week.

Fast forward a few weeks.

The second CEO asks me the same thing.

A few more weeks.

A third one.

A few more weeks.

Fourth one.

A couple of those, by the way, are still working with me now, and it's ten years later.

And when it was that easy and was that quick, I'm old enough now that the ego filter for me is way lower.

If this had happened in my twenties, I would have thought I would go to puff my chest and said I'm so special.

But instead this happened when I was 40, not 20.

And my reaction instead was that of an entrepreneur.

If this is this easy, then there's a gap in the market.

It's not me.

So this was the third force.

I started to talk to founders, and what I started to learn was all founders seem to ask the same questions.

They ask them at the same stages of company building.

They are alone in this journey.

And to be a startup founder, to be a startup CEO appears to be the only job I can find in the world that is incredibly highly paid, that has no training or pedagogy.

Good luck CEO.

Hope you learn the job fast enough or you're going to get fired or your business will fail.

And that was crazy to me.

So I had this force number one that said, I love to teach, I love to work with founders, and I want a lot of personal freedom.

I had this force number two that said, company building always seems to be the same.

And I had force number three of founders raising their hand, saying, someone teach me.

And that led to the foundation and the formation of enjoy the work, which is a firm I have now had the great privilege to run for the last decade.

Hi, the podcast you are listening to is a companion to my recent book, tech startup how to launch strong and exit big.

This is the book I wish I'd had as I was founding and running eight startups over 35 years.

It's like a memoir of my entrepreneurial journey.

I tell the unvarnished truth about what went right, and especially about what went wrong.

It's for the founder, the CEO, and wannabe founders of tech and non tech startups.

You could get it from all the usual booksellers and also from the publisher@manning.com.

dot.

I hope you like it.

It's a true labor of love.

Now back to the show.

So in ten years of this, this firm, which is of course itself a startup, so, you know, it gets added to your list of you've got a belt somewhere that you've got notches in, right?

How many founders do you think that you've, have you kept?

Do you have an actual count or just a rough idea?

How many have you worked with?

The blunt answer to that is more than 160 startups and north of 300 founders.

The slightly more nuanced answer to that is, for the first couple of years, Jeffy, I did it myself.

I was feeling this call that there was something bigger here than just me, and faced this question of, do I wanna be an advisor, or do I wanna build an advisory business?

Cause they're entirely different things.

My wife Jane asked me what ended up being one of the more profound questions of my career, where she asked me, would I be okay not building this business?

And when I sat with that question, the answer ended up being no.

I was feeling called, I needed to build this.

And so that led me to bringing on my first partner.

His name is Anu.

He and I spent a year thinking through, structurally what would have to be true about enjoy the work to attract incredibly successful former founders who now wanted to be teachers, who now wanted to be confidants and mentors and coaches in a professional way.

Not the hobbyist crap that's everywhere out there in the world, but the craft of how to train and support a CEO.

And so we spent a year building that infrastructure, from the boring stuff of accounting and legal and economics to what is the service model?

Well, how do we market ourselves?

How do we sell this?

How do we present ourselves?

What are the different platforms and pieces to what a CEO needs to learn over time?

We figured that out over a year, and then we started to add partners.

And now I can tell you, it's myself and ten other partners.

I run the firm with another managing partner.

Her name is Leslie Fine.

We have an operating staff of another ten folks, and we currently today support over 60 active startups right now, but have worked with, as I mentioned, 160 since our founding.

Do these startups pay you in cash, in equity?

Some of both.

The short answer is yes.

We get compensated both with a cash retainer as well as some equity in the business.

And it's all kind of de risked for the founder.

We spend a couple of months getting to know a company before willing to say yes to them.

We have more founders interested in us than we can say yes to.

So we're very precious about who we're going to work with, the name of the company, enjoy the work isn't an accident.

Like, we have to enjoy this, we have to know we can have impact.

We have to have the kind of human across from us who's kind and ambitious and will work hard.

And we don't have to try and teach them motivation because we don't actually believe we can teach motivation and that they have to see enough value in us that they're going to part with their time and with their money and with their equity.

And we get paid in all those dimensions.

And are the VC's or other types of investors involved or are you able to just interact with the founders, the CEO?

They get to make the decision just like they would if they were deciding which legal firm to use, which bank to use.

Yeah, this is a rather controversial statement sometimes from us, but we 100% work for the CEO, we don't work for the company, even in that way.

We don't work for the board, we're not board members, we don't have fiduciary, we work for the CEO.

And we do that very purposely because, and this is one of the questions you had asked me when we previously met you.

I think what are some of the uncommon things that show up in the world?

One of the things that I noticed in startup life that was both obvious and revelatory.

There's no one entirely on the CEO's team.

No one is fully safe.

If you are on the preferred shareholder side of the cap table, you are not fully safe.

If you are a board member, you are not fully safe.

The employees, you can't disclose and say everything to them.

Oftentimes your co founder doesn't always feel fully safe.

Your spouse doesn't always feel fully safe.

That heavy is the crown.

The CEO feels very alone.

We, everything in the way we structure our work, structure our contracts, and the way we energetically and culturally show up is we are on the CEO's team.

However they want to deploy us, use us, treat us, we're in.

Yeah, it was a shock to me when I was CTO at one startup and the board decided that the CEO had to go.

Put a lot of pressure on me to slide into the CEO role overnight, and it was my first time as CEO.

Everything overnight changed.

The people I used to interact with on a daily basis changed how they talked to me.

The board members changed how they talked to me.

It's when I learned the adage, the board is 100% behind you as the CEO.

Until there's 0% behind you, there is no in between.

It was a shock.

After a while I understood it, but it was a shock.

It is.

It is.

And this was the revelation for me, in part for starting this business that there's so many aspects to the job that right now, founders are expected to learn, just through trial and error, of doing the job while trying to run a business that most of the time only has twelve or 18 months of capital left before they have to get to a next inflection point to raise more money or get to profitability yourself.

They're on this incredibly difficult clock while having to learn a brand new job with no one teaching them anything.

Look, hope you read the right blog at the right time, ask the right question at the right time, or you're dead.

Or maybe this book will help.

Yes, exactly why I wrote it.

It's exactly why I wrote it.

And that is powerful for folks who learn that way.

And there's also this connective tissue Jyothi of like the book is powerful.

So now, how do you overlay what you teach in your book with the reality on the ground for a given startup?

And that's the translation layer that we try and play, of taking brilliant founders and successful operators like yourself, who have put their content out into the world.

And now the founder raises their hand and says, I have 45 minutes to solve this problem.

Which framework should I use now?

How best do I employ it?

How questions do I ask?

How do I make this efficient?

And so what we see as our job is to read all the great material, like the book you're producing, be able to figure out, how do I operationalize this in the moment with the founder in front of me when they're standing in the arena?

Oh, absolutely.

What you're doing is absolutely essential.

And it's sort of a shock that it hasn't occurred to anybody else to do it.

One of the things that I would say, and it's nice of you to make compliments about this book, but it's my experiences.

And yes, I had nine startups to gain these experiences, but now you've had 160 or 163 hundred founders.

Sort of in my much smaller way, I'm trying to add to the stories that are mine.

I, in the book, this podcast where now you're like my 47th guest, and so I got 47 other experiences recorded.

But again, your point is there's nowhere that it's gonna say to the c, to the CEO that's got a particular situation, oh, go look at this podcast and go to, go to minute 24.

But yeah, what you guys are doing is great.

Now, are you staying geographically in California, or are you helping all over the.

And I've told you a similar percentage of the founders that we work with.

I was convinced of two things.

And the good news is I was only right about one of them.

I was convinced of one.

Our founders are not going to leave us like we are medicine.

We are not yet supplements.

We're not vitamins.

And as the business world got harder for them, raising capital got harder.

Exiting got harder.

Selling got harder.

Managing your remote team for the first time got harder.

We were more important.

I was convinced, like, we're not going to have any churn.

And I was right.

But the second thing I was convinced of is we're not going to sign any new founders if they can't sit with us, if we can't sit in a coffee shop together.

No one does big, important transactions over video.

That's not a thing.

It's amazing how that world has shifted.

Massive enterprise contracts getting signed around the world when people have never met.

So now fast forward, I think five years later and only five of my partners, including myself, live in the Bay Area.

We now have partners in North Carolina, Lisbon.

We had a partner in Scotland last year, partner in New York, Pittsburgh.

And our founders.

We have more founders in Tel Aviv than I have San Francisco.

We have Karachi, London, Berlin, as well as San Francisco, Montreal, New York.

It no longer matters.

It doesn't matter where we are.

It doesn't matter where they are.

With some time zone issues occasionally.

I was spending time this morning with two founders who are in Sofia, Bulgaria.

and my skills are diminishing by the day already.

it's kind of tough.

In the 33 minutes we've been talking, I've seen examples of where you have developed, or maybe you were born with it, I don't know, a lot of grit.

And that's true of anyone who does a startup.

And you've done multiple.

Do you think you had grit from a very early age or was there point in your adult life that you think, oh, well, this is when I first started to exhibit grit.

I was a lazy student for most of high school and college.

I coasted by on some ability.

What I reflect on is that if I was interested in the topic, I was all in, loved it, consume it, and if I wasn't interested in the topic.

No matter how important it might have been to a transcript or a story or resume, I couldn't be bothered.

And I would do whatever the minimum possible was to just survive the class.

I didn't have grit yet when I got out of undergrad and had my first adult job.

And like, I had tiny things before that, but like, my first, like, hey, it's on me now.

I was in a topic I cared about.

Like, suddenly like, I want to be better at this, I want to do well at this.

And working hard became very easy.

Now, if you ask me where that came from, that came from my dad.

Both my parents have always worked hard.

My mom was full time while taking care and raising two children.

My dad is uniquely gritty.

He ended up having an issue with his leg when he was twelve years old.

That got bad enough where under emergency surgery he had to have his hip removed and his leg fused directly to his pelvis.

So he lived most of his life with no hip on one side and one leg slightly shorter on the other and therefore no joint, no cartilage, no nothing.

He was a eight out of ten, if not higher on the pain scale, most of his young adult to mid adult life.

I didn't understand this, not until I was much older, but he'd have like an hour commute every day to work.

He'd be in that kind of pain.

And while he was a professor, he then started a consulting business on the side.

The consulting business did so well that he got hired into bigger and bigger roles in a wholly different industry.

Left consulting, moved the family, did incredibly well for himself professionally, all while surviving this pain that when he was twelve to 13, had to spend almost a year in a full body cast at home in a one bedroom apartment with no air conditioning in the Bronx.

My dad's fucking gritty.

So, nature versus nurturer.

My parents raised me and my sister where we wanted for nothing.

There wasn't grit in my childhood.

Our jobs was to be good students, and I did that in a mediocre fashion.

My sister was a much better student than me.

But when I got out of college and I started to care about my profession, that was forcing function one.

And then I.

My father's DNA kicked in from there and I've been gritty ever since.

In every aspect of my life I'll share a story that one of my partners shared with me that I've loved and I've kept it in my heart ever since.

And this will be me.

He shared a story that when his kids were not three but older than that.

Call it seven, eight, nine.

He would give his boy and his girl, like, challenges, physical challenges, with a reward on the other end if they could accomplish it.

And one particular year, the challenge was if they could ride their bikes up the neighborhood hill, which is really, really hard, they could get to the top of the hill.

Then there was like a special vacation on the other side of it.

And his son is the kind of character that says, I'm the terminator, nothing will stop me.

And so his son just every day, kept trying and trying and trying.

No complaints, just kept trying.

And his daughter hated it.

Hated it.

Every day.

Every day was tears.

And eventually, through all that tears, through all that misery, she did it.

But my partner was making a bet that this was something that could actually damage his relationship with his daughter.

This could actually harm, this could actually cause maybe lasting trauma or lasting breach, but that the long term benefits towards her resilience would be worth it, even at the risk of his relationship with her.

And feedback loops are long.

He didn't know if it would pay off.

Fast forward a decade, and I'm not going to let the facts get in the way of a good story, because this is his story, not mine.

But I'm loosely right about this.

It had such a profound impact on me.

Fast forward a decade, and his daughter's writing her college admission essays.

And she writes an essay about having to ride that hill that summer and how unbelievably thankful she is to her dad for that lesson.

It could have gone the other way.

What would he have done if one of them had succeeded?

The other hadn't.

Were they going to leave the other one behind when they went on the vacation?

They don't know that answer.

They don't know that answer.

He was so sure they would both do it.

He was so sure that it was worth it for my daughter.

All I'm trying right now is to reinforce that we make decisions as a family and how important it is to be kind amidst what are often, for a three year old, overwhelming emotion.

And so that when she calms down from those explosions because I've said no to something, I'll say to her, it's time to say, please, it's time to be kind.

Time to give each other a hug.

It's time to share.

And that's why daddy said no.

And I still love you, and I'm sorry you're upset.

And I will let her have those feelings and I won't try and cut them off.

And then I'll come back to how can we be kind?

How can we take responsibility in these moments with words that a three year old can grasp?

I don't know if that's the right thing.

It feels right.

The other job that there's no training for is parenthood.

But there's a lot of advice, man.

All right, well, this has been absolutely delightful and fantastic.

I am really appreciative for your time.

That's a wrap.

Thanks for tuning into this week's episode of the designing successful Startups podcast.

Check out the show notes for resources and links.

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This is Joffrey Rosenberg saying tTFn Tata for now.