Knowledge comes with experience, and Jeff Leventhal has 25 years of experience in the tech startup world, including leading five companies from idea to exit and investing in many others. It’s an understatement to say he’s learned a few things on his entrepreneurial journey.

Leventhal’s great professional passion has been using technology to facilitate the delivery of professional services. His current iteration on solving this problem is WorkRails, a SaaS solution that helps other software companies sell and deliver their products. He’s also a Partner at BOLDstart Ventures, a “first check” investor for enterprise software founders.

Leventhal is great at telling engaging stories, and he transfers much of his wisdom through personal anecdotes. He shares some of his best tales in our interview, providing insights on acting in harmony with your internal wiring, socializing your business ideas and evaluating feedback, and building a team that will impress investors.

My thanks go out to Leventhal for letting me pick his brain and giving me with a few good laughs during our conversation. Check out Leventhal’s LinkedIn page to learn more about his long and impressive career, and have fun listening to this episode of Powderkeg: Igniting Startups.

In this episode with Jeff Leventhal, you’ll learn:

  • Why big career decisions often come down to your personal “wiring” (5:07)
  • A cheap, easy way to perform market research (11:12)
  • The six “value creation moments” of a startup (14:38)
  • How to win over VCs with the strength of your team (21:52)
  • High-level tips for socializing your ideas and receiving criticism (27:34)
  • Why New York City is a natural environment for entrepreneurs to flourish (33:44)

Please enjoy this conversation with Jeff Leventhal!

This episode of Powderkeg is brought to you by DeveloperTown. If you’re a business leader trying to turn a great idea into a product with traction, this is for you.

DeveloperTown works with clients ranging from entrepreneurs to Fortune 100 companies who want to build and launch an app or digital product. They’re able to take the process they use with early stage companies to help big companies move like a startup.

So if you have an idea for a web or mobile app, or need help identifying the great ideas within your company, go to

If you like this episode, please subscribe and leave us a review on iTunes. You can also follow us on Soundcloud or Stitcher. We have an incredible lineup of interviews we’ll be releasing every Tuesday here on the Powderkeg Podcast.

Jeff Leventhal Quotes from This Episode of Powderkeg:

“Closing doors may force you to leverage skills inside you that you didn’t even know you had.” — Jeff Leventhal

“When you’re doing a startup, nobody wants to hear from you. Be prepared for people to tell you your idea sucks.” — Jeff Leventhal

“I look at my business plan as a work of art. The same way a musician looks at a song, or an artist looks at a canvas, my business plan is my canvas, and there’s vulnerability when you show it to somebody.” — Jeff Leventhal

“Entrepreneurship is not a career choice. It chooses you. It chose me, and I’ve done it, and it’s hard.” — Jeff Leventhal

Links and Resources Mentioned in this Episode:

Companies and Organizations:

Information Builders



VC Firms:

BOLDstart Ventures


Coworking Spaces:


Software and Apps:



Cornell University

Stanford University

Trade Shows:

PC Expo


Jonathan Lehr

Jeff Bezos

Did you enjoy this conversation? Thank Jeff on Twitter!

If you enjoyed this session and have 3 seconds to spare, let Jeff Leventhal know via Twitter by clicking on the link below:

Click here to say hi and thank Jeff on twitter!


What stood out most to you about what Jeff shares in this podcast?

For me, it’s why big career decisions often come down to your personal “wiring”.

You? Leave a comment below.


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Episode Transcript

Welcome to Powderkeg igniting startups episode 23 with Jeff Leventhal. He’s an experienced software entrepreneur and CEO with a 5x track record for starting and exiting software companies. But now he’s a venture partner at Bold start ventures in New York City. And he’s also the co founder and active CEO of work rails. Needless to say, this conversation is very interesting. I am your host, Matt Hunckler. And I’m the founder and CEO of verge, which is the network of local communities with global reach for tech entrepreneurs, investors, and top talent. Each guest has their own powder keg full of raw skills and talents that have been ignited their startups and fueled their growth. These are their stories, you can find me on Twitter and on Instagram at Hunckler. And that’s Hu NCKLE are and what I want you to do is let me know how verge powder keg, and I can help you with your entrepreneurial journey. You can also find all of the transcriptions the show notes, all the links to everything we talked about each and every episode, including this one. And of course, you can subscribe to make sure you don’t miss a single thing. This week’s episode of powderkeg is brought to you by developer town. These guys have been friends of ours for years, they’ve helped so many startups take their ideas to market gain traction, and build and grow and meet customer needs. But something you might not know about developer town is that they actually help enterprise companies move like a startup. Corporate innovators often work with developer talent to explore software solutions that support their business needs. And now, the cool thing is developer town leverages all of their years, you’re working with startups, and they can help companies better understand the viability of potential software solutions, apps, products that they’re doing digitally, and quickly bring them to market. Developer towns created this proven sprint to market process so that large enterprises can move like a startup. You can find out more about developer town read up on them at developer That’s developer town all one word powderkeg. All one word. Again, that’s developer Developer town, start something. Our guest today is serial entrepreneur, Jeff Leventhal, who has one of the best energies I’ve ever been around. Now, I know that sounds a little bit out there. But he really does have some kind of X Factor. So Jeff is a builder of companies that are market moving businesses. And he has successful exits, including on force spin back and work market. But he currently is the CEO and co founder of work rails, which is a software platform for professional services. But Jeff’s story is so cool, because it’s full of great entrepreneurial knowledge from the trenches. And it’s packaged in these just amazing stories from early childhood wins to some of the most common traps that many entrepreneurs face. Jeff packages it all in really, really great stories. The other cool thing about Jeff is that he’s also an active investor in over 20 startups. So he brings a unique perspective, as someone who wears both the CEO hat, as well as the venture capitalist hat. You’re gonna love this guy. So let’s just get into it. Let’s set this thing off. First of all, welcome

to the show. Thank you appreciate it.

Can you tell us where we are right now.

So today, we’re at the workbench headquarters in New York City Workbench is a enterprise software community. It was started by a gentleman named John lair and it was started as a fund. And it was started as a place for entrepreneurs to explore their business ideas and get validation for the right years, potentially raise money meet investors, meet like minded professionals that are working in the same environment solving similar types of problems. And so it’s a community more than anything else around enterprise so far in New York City.

That’s really cool. That’s cool that like a niche like that has something as big and expansive as this. Yeah, exactly. Well, I know your tech career goes back 20 plus years. That’s right. I imagine there wasn’t anything quite like this when you got started.

You know, in 1990, when I landed here in New York City, there were obviously a number of software companies. I actually had the fortunate opportunity to work for one of them. It was called information builders, and still a fantastic company today. They build middleware applications. They build focus, BI applications, and it was a thriving great business in New York City. And it was an enterprise software company in 1990. Wow,

what did you join that company to do?

So software development. And it was a time of my life where I was in college, but economics and resources and things that were going on in my life, dictated that I was better off leveraging my self taught software development skills, then finishing college. And so my personal circumstances pointed me in the direction of getting a job instead of finishing college. You know, those technology skills, you know, they are transferable they’re usable in lots of environments. And I ended up in New York City and information builders building software. And

at 90, what was that decision making process like for you to make that decision to quit college, which I imagine wasn’t a small decision in and of itself.

It wasn’t a decision. It was just circumstantial, yeah, more than anything else. But you know, when you’re living through something, it’s very different than looking back and reflecting on it. And so living through it, it felt like all the right natural things for me to do based on the things that were going on in my life. And so it was, it was a series of obvious choices for me. And I had the opportunity to sit down with somebody on my team recently. And he said to me, Hey, I’m, I’m three quarters through college, should I finish it tonight? You didn’t finish? Jeff, you’re successful? Why should I? And, you know, I went through a whole story about wiring and circumstances and timing. And I don’t think that they’re, you know, I think that they’re the right reasons to leave college. And there, there are the wrong reasons, but they’re very personal. And each person needs to really think through for themselves, I knew I was wired in a way that it wasn’t going to change, what I needed to learn to do, what I wanted to do wasn’t going to come to me through a college experience. And so for me, when I was, you know, thinking about my future, when I had the opportunity to get started, or really the requirement to get started, it all felt good. And my advice to this person was, you’ve got to really think about your internal wiring, because you will close a lot of doors by not having college, but you may learn a lot of things about yourself. And closing those doors may force you to leverage skills inside of you that you didn’t even know you had. And it may bring out something inside of you, that’s really special. So you know, go home and really think about your

wiring. I love that way of like thinking through it sounds like someone with a technical background, how they might describe your internal thought processes. And, yeah, I mean, internal wiring is a great phrase for that. What are some of the things that you do or have learned to do to help better hone in on what your internal wiring is now and what it’s telling you to do next.

I’m an entrepreneur. And I didn’t, I didn’t call myself an entrepreneur up until a couple of years ago. And you know, this is 26 years in the making, this is five companies later, a billion plus dollars in exits, you know, lots of venture capital, and I didn’t even think about calling myself an entrepreneur have a lot of respect for the word. And so, you know, what I do, you know, is something that feels natural to me, it’s, you know, is it a creative process? Is it a, you know, it’s never for the money, right? It’s, it’s about solving a problem. And I feel, you know, in looking and going through my day, there are a lot of problems you encounter. And then there are just certain ones that I’m interested in solving. And so if that’s what an entrepreneur is, and that’s what I am using, that is how I think myself now finally, after 26 years of doing this,

no five plus exits, all really impressive exits, I had to just do a little research before we our conversation to one, congratulations. That’s huge, too. How do you decide what problems you’re going to solve? There are a lot of problems out there. Yeah. And I imagine you see a lot of them. Are you collecting those somewhere? And then? If so, how do you then decide which one or a couple of ones to go and aim, your focus at

my life’s work has been at the intersection of human capital and technology? And some reason I was always fascinated by companies early on? Well, I mean, really early, young, as a young kid, looking at companies that had low employee counts, but really high revenue. And like, wow, how are they delivering such productivity with such a small team? This is you as a kid talking like this is this is reading the top 1000 companies in Forbes magazine, and looking at the employee count column versus the revenue

column. Yeah, I know exactly what you mean this thing, but like, you know, this

company has 2000 employees, and they’re doing 10 times the volume of this other company with a much bigger base of employees. And so that was really interesting to me, I built a software platform that allowed companies to identify problems using a software platform. And when they identified these problems, they had a hard time of solving them. And so to me, you know, it’s kind of like, well, don’t you just call up a service company, they show up and they go and fix the problem for you. And it didn’t work that way, naturally, you know, they call the company, the company would try to find somebody, I became fascinated with this logistics problem of getting the right people to the right place at the right time to perform a service. And the only way to really do that was to apply technology to each step of that process. And so my life’s work has become making those processes better football, and first, really, first and foremost, for the for the person performing the work. Because if you can do that properly for that person, the outcome of that work is going to be amazing. And so each of my companies has been an iteration or an inspiration from solving that problem.

What were some of the big breakthroughs and without maybe giving away some of the secret sauce, what were the what was the secret sauce in some of those early companies where you saw that intersection of technology and human capital and said it We just approach it in this way, that’s gonna give us the edge that we need to compete and dominate this marketplace.

Yeah, you know, I think of that in the context of the way you think about the car that the Flintstones drive, right. And so they’ve got this car, it’s got almost no roof, no windows and no motor, right, it’s just feet running along. And I look at it, I look at building software in a similar way, right. And so it’s like, you know, you can start out with a basic framework to solve a problem. But there’s gonna be a lot of things that are gonna get bolted on to that framework as you learn by listening to clients. But then as you can learn by listening to customers, all the nuances to how somebody should show when they should show why they should show up how a person wants to receive work, when they can do work. And by listening to yours was in twice as much as you speak by really listening to it with the clients are asking for, you can actually develop a product and address a very, very large problem. So you know, I believe in putting something out there pretty quickly and getting a lot of feedback. And it’s not that I believe a customer should necessarily drive your roadmap. But I believe you’ve got to listen to the market that you want to address with your solution very, very carefully. So don’t build too much. Don’t box yourself into a corner, get something out there, get in front of people socialize it, tell you one of the things about that is that I was at a trade show on Wednesday, because I specifically flew out I had this new idea, I wanted to really build an online marketplace for solving work problems. Nobody had ever really applied jobs to a marketplace before this was late 1990s. And so I went out to the PC Expo trade show in Las Vegas. And I said, I gotta go talk to people in the industry and try to understand how they solve these problems. And so I literally went to every single booth while and I and naturally the tradeshow people said, Well, would you do? And so I, I pitched the concept. But what I wanted to do, literally 1000 times over the three days, you know, each booth, I knew I get asked that question, I wanted to just see how the concept would resonate? Well, I have software that helps people show up and fix things. You’re building technology, you ever have to get people in the field to fix things? Well, yeah, we do it well, how do you do it? Right? And so I would say something and they would look at me strangely, and I would know. Okay, let me let me change that a little bit the next time. And so over the course of three days, I actually ended up with a really good framework on how to build this software. And so it was incredible market research 1000 potential customers in one spot that I had to pitch over three days. And actually we were the great business plan

that is an awesome sort of trial by fire. Almost like customer development, Crash Course,

research, focus group, these things cost a lot of money. But that tradeshow was free to attend, I had to pay for the hotel room with a mirage and get myself across the street. And that was about it. That’s incredible.

What do you remember that specific pitch. And when I say that specific pitch, it sounds like it changed quite a bit, where there are key moments when you changed one thing, and it just changed the way the conversation was happening.

I don’t remember the actual specific things. But here’s what I do. Remember, I printed business cards with no name or phone number, just a web address. And the web address at the time was computer And it was interesting to me one, how I would introduce myself, but you know, almost immediately they would forget your name. So they were looking on this business card that I had handed them for my name. And they’re like, they would say there’s no name on here. And I would say yeah, just go to the website, you don’t need to call me just, you know, go to the website. And that was a little bit impersonal. You know, that was something I walked away with, Okay, I gotta, I gotta have a business call my name on it, right? I can’t just have the website URL, and hope people are going to just go there. And so it’s not lost on me that in selling anything, there’s still a bit of a relationship that matters. To me, even an Amazon, you know, I guess everybody feels like, we know Jeff Bezos a little bit. Right. And you know, there’s a brand behind that big machine.

Absolutely. That the pitching process, I think is an interesting one. Because it’s something that whether you do it naturally, or it’s a learned skill, entrepreneurs have to develop that ability to pitch Do you think that that’s an innate quality that entrepreneurs have? Or do you think it’s more of a learned skill?

You know, I’m gonna guess, you know, more of a learned skill. And I would, I would think, though, true entrepreneurs, and I use that word entrepreneur very, very selectively and carefully. I think an entrepreneur, somebody who actually creates value, you know, if you’re going to open up a dry cleaner, I’m not sure that that is value creation, I think that’s just exchanging one job for the other right entrepreneurs are people who truly create value. How do you define value? One plus one is for you know, how do I take a certain list of ideas, mix them up with another list of ideas from another industry, and all of a sudden, these two things have converged and something much better has come out of it?

Do you have a specific metric that you look at? Is it market cap? Is it revenue? Is it employee count?

I don’t have a specific metric that I look at, but I have a framework that I think within Can you talk me through that? Yeah, it’s the idea, the team, the product, the first day you sell it, and cash flow, breakeven, and then the exit. Okay? And so each of those are value creation moments, and those moments in a business can happen. Over the course of 10 years. They can happen over the course of two years, even a year sometimes comes. But when you have an idea you’ve created value maybe in your own mind, right. But yesterday, you didn’t have that idea. Today you saw this problem, you have an idea on how to solve and you know that there is some value to that may not be a lot of value, maybe a huge amount of value, right. But there’s value to that idea. And then if you can, actually, and I put team next, but if you can actually convince some other people, this is really good idea, and they shouldn’t give up what they’re doing. There may be a little bit more value to what you’re doing, right. But between that idea, and getting ready to sell somebody else to come along and perform this idea with you, or build this company with you, you’ve created some value that if you can actually convince people to join you, I mean, these people are going to be smart, they’re in the industry potentially, they’re giving up something else in his opportunity cost. So I’m looking at as okay, this guy had an a great idea. And he’s convinced three really smart people to sign up and do this with that person. And then can that team of four people now sit in a room and build a product? Right and so but everything in between these value creation moments is an absolute slugfest?

Yeah, one has a pitch to right, like pitching someone to join you on this? Yeah. Do you remember the first time you convince someone to join you on a on a venture?

I do. I

do. Was it what was the vision?

This was in high school, or, you know, high school and in the neighborhood that I lived in, there were a lot of there were a lot of there was a lot of new construction. And so when you go to a neighborhood and you you see this new beautiful model home, it’s got all these bells and whistles and features when you actually buy it, there’s no rear deck. There’s no there’s there’s a lot of things in that model has it you don’t get in the way you buy. And so all this new construction had gone up in my in the area that I lived. And I was like, all these people need tax. None of them have tax and I you know, I didn’t know anything about deck building. But here’s the problem, right? Yeah, these people need to x and I’m gonna go door to door and I’m gonna go and sell decks. Yeah, good idea. So so so it was presented to me. Yeah, lo and behold, somebody, somebody sent you all in fact, yes, we do want to get a deck, can you you can build a ton of like, Absolutely, I can build you want, tell me what you want. I took some notes. You know, we mentioned out their backyard. I then went to the bookstore. And I bought the timeline Home Improvement Series books on how to do these. So you had

no context for building decks, you just new decks needed to be built zero. And so

it was a 26 volume set, I went to D went to the deck section, I started to learn how to do this, I got to the posit, they ordered the lumber, it got delivered. So far, everything was going pretty well. I skipped over a bunch of steps, like getting licensed or insured, or incorporated. But uh, I had this company called Long Island decks, and they were there and building a deck. And so first day comes, I got my pull digger, I’m digging holes for the posts, you know, I’m pouring the concrete. And it’s a lot of concrete. It’s a lot of posts, and I come back the next day, and they’re all crooked. In a lot of concrete, I’m like, I was excited about it. So I’m like, I’m gonna put extra concrete it I want this to be good. And so I come back and all the posts are crooked. And so I’m like, Oh, this is not good. I’m gonna get out of the car and I bought. So I bought the car for 500 bucks. I rode my bike, I sold this car on the side of the road for sale, I rode my bike to the car, I didn’t have a license, I bought the car, I drove it home, I put my bike in the back of the car. My parents have put this in the driveway and I got a car. So I’m sitting in this in this in this station wagon with most of the cards didn’t even work. And I’m looking at him like I this is a problem. And I put the book on my front seat and I’m like, I’m going through them and what did I do wrong and the wife comes out, she like my husband wants to talk to you. She hands me the cordless phone. And he’s like, if you leave now nothing bad will happen. He’s like, it’s clear, you have no idea what you’re doing. Like just leave the wood and just leave the project. And nothing bad will happen. I was like, Alright, I get no problem that your would good luck getting this fix, I’m sorry. And get out of jail free card, but actually figured out what I did wrong until I convinced this guy in my high school. I’m like you don’t understand everybody decks. They’re actually I figured out how to deal with an action not that hard to do. I know what I did wrong. Do this with me.

So this didn’t dissuade you this, this first failed project. Now let’s get

so his name was Scott. He’s a very successful lawyer. And he lives on the West Coast today. And Scott and I went to you went on to build a very, very nice business, building and maintaining and power washing decks over the next three years. And ultimately, we sold the business. And it was a great success story.

So what was the pitch frame? The pitch format? Do you remember when you first talked to Scott about this idea? It was was it more about like, this is the opportunity here people are gonna be buying decks from somebody it may as well be yes,

we can do this. This is a great summer job. You know, power washing is a great thing to do in the summertime. What better choice do we have? Let’s go do this. And I gotta tell you we had we had a blast we ran and they had in the paper we were giving out estimates we were driving all over the place and we built a real business and we had five people working for us at any given time. We learned a ton that’s really Yeah, I have all the photos and estimates and all the copies of the estimates at home so I took a lot of pride in looking at them

did that business have the that last stage of value creation the exit?

So yeah, so the business was successfully sold I think it was like 120 grand. So and it’s still in business today. So really proud I get to drive by with my wife, she is the same story every time I kid you like, there it is kids. That’s the company that bought my business. They’re still in business today. So really awesome. Every company I started is still in business.

Wow. Okay, so now now I want to I want to dig in a little bit on the pitch, because clearly, you’ve got some practice at the pitch, if you’ve been doing it, since you’re in high school, five companies later, you’ve invested in a lot of companies as well. What makes a good pitch?

One, it depends on who you’re selling. And why you you know, I’m assuming you’re talking about convincing somebody to come work with you.

Sure, look, it could already be it could also be VC, let’s let’s dig into VC because that’s such a VC angel investor pitch. Because that’s such a critical point in the lifecycle of a company, it’s where they either gonna continue to sputter along, or fail, or really take off if it’s a venture backed. Yeah. bankable business. Yeah. Talk me through that pitch, how do you first decide who you’re even going to pitch to?

Yeah, so look, if you want to raise money from venture capitalists, there’s literally 1000s of firms. And so if you’re building a software company, don’t pitch a VC that invest in biotech, right? So so make sure you know, the firm you’re pitching. actually invest in your space. A lot of people actually don’t do the homework. You know, they think VC read the website. Yeah, read the website, read about the partners. And again, if you don’t have a clear, concise way of getting yourself to at least 100 million of value, VC may not be the right choice. Yeah, there’s a lot of money in VC say there’s a lot of pressure for returns. And there’s a lot of pressure to take a lot of capital in a business that has a really good opportunity. But if you can’t really see how this becomes worth 100 plus million dollars, VC may not be the right way to go. But if it is the right way to go, and you think you’ve got a tiger by the tail here, and you can build something big one, make sure you’re pitching somebody that’s gotten knowledge and expertise in your space. Number two, make sure to really articulate the market opportunity that’s in front of you, and how you’re going to actually be able to address that market. Number three, demonstrate how you this is the perfect team to back for this market opportunity. This is if you’re going to back a team, this is the team to back this and why this is a team to back either you’ve learned something special, or you’ve done something before or this team has worked together before. And there’s no team risk, and they’ve got domain expertise. But that VC most likely is looking at a few companies within the same ecosystem. And they’re gonna probably just pick one. And so really, why is this the right team to go figure this out? When you’re looking

at that team? You mentioned some things like domain expertise or prior work history? What are some of the other things that are positives? And then on the contrary, what are some of the like red flags for you where you’re like, This could be we could be in for a rocky ride if we invest.

So, you know, one, you know, are these entrepreneurs prepared to chew through brick walls? Yeah, right. You know, candies, do these people really have what it takes to you know, and I look at it in the context of physical, financial and mental strength. Like when you’re the company already takes your call, when you’re doing a startup, nobody wants to hear from you, right, like, be prepared for people to tell you your idea sucks. Nobody wants to hear about it, and they hang up and go take another call, right? Like, if you can’t handle that, this may not be something you want to sign up for, physically, you know, just the sheer amount of work you’re going to do to pull this thing off is enormous. Right? And financially, you need to not want, right, like if you’re a materialistic person, and it’s more important to you to go lease a nice car and do all these other things. Like you need to sign up for economics that are really, really stringent and tough. But you don’t want to put yourself in a position where you’ve got lots of bills and expenses and obligations, and then go try to call up a startup, like you’re setting yourself up for a hard time. So I want to see that somebody’s got the physical, mental and financial and financial and financial strain, that just not suckers for wanting shit. They can, you know, they’re gonna just be able to not have their back against the wall and do what they want to do. And when your backs against the wall, you don’t always get to do what you want to do. So those I looked at those three things, also, one of the things, you know, like, early on, I would take guys out and I’d say, All right, I want to see if you can think of that girl, you know, into somebody for a sales job. You know, if you can’t sell yourself, you’re not going to go sell my product. Yeah, right. Like I want to understand somebody’s confidence in in a room like that. And in a cold environment like that. If you can’t sell yourself, you’re not going to sell anything else. Yeah. Right. So I want to see that people have the strength to

do pretty well. Yeah. Yeah. Especially if they’re self reflective. Yeah.

Some of the other attributes that I think are the pillars of a great entrepreneur,

you mentioned physical strength. Yeah. And I know your soccer player. Yeah. Talk to me a little bit about some of the parallels you see between sports, soccer, physical strength and financial business strength from from a model standpoint, or are they completely different things and it’s This is an outlet. And this is business. And

I haven’t really given a lot of thought to the convergence of entrepreneurship and playing sports, I guess you can draw some analogies around team. But I don’t see that because entrepreneurs kind of, you know, I think they’re more individual sportsmen, you know, they’ve got, they’ve got a beacon that’s driving them, not every is always sure why it’s driving them, you may not even be sure of what’s driving you. But I haven’t really thought a lot about the convergence of team sports and entrepreneurship, necessarily, when I think about physical strength, I think about it in the context of, you’re just not going to sleep a lot, right. And so when you when you do get a little bit of time to yourself, you know, you better use that time carefully, be healthy, set yourself up for success. Don’t eat junky food, and make sure that you’ve given yourself the best advantage by being healthy and smart about those kinds of things. So you can execute properly.

So obviously, being in that physical state is gonna allow you to go from pitch to pitch, have the door slammed in your face over and over again, stay polite, preparing a deck,

and I’ll share a story with you about the mental side of it, like people are going to tell you your product. Exactly, you know, too little stories. One is, I hide this executive from Hewlett Packard once, and he’s amazing. I said to him, I go, and this is, you know, we were first getting started, you know, it’s like his first week work. And I said, you know, three quarters of your Rolodex aren’t going to call you anymore. He’s like, What are you talking about? I’m like, Well, you know, your, your Packard, when you call people, they take the call, they call you back, they’re interested, you know, you’re a big company, and go, nobody knows who we are. When you call them, you know, you’re gonna see that 25% of those people actually like you, right, and the rest of them whenever you have a packet that was hard for him to really comprehend. But in high school, I used to write poems and songs and things like that I would share with people and people were like, Oh, that song is terrible. I like, that sounds terrible, right. So one day, I took the song, the lyrics of a Paul McCartney song, and I wrote him down, like, what do you think of this song? And they’ll ask marijuana was always going to nobody’s gonna like that song. Right? And that taught me to stop really listening to feedback, and really follow my own. Because I’m, like, I said, I’m having all these songs I’m writing be bad. Yeah, I got all these things I’m putting together not make sense to people, right? But people are very happy to be negative on you. So someone’s like, Alright, I’m going to take this, I’m gonna take these good lyrics, I’m going to present it to the same friends. And they’re like, that’s terrible. I’m like, okay, I’m good. Now. Now I get it.

That’s interesting. Because on one end, you’ve got sort of the Don’t believe everything you hear, because people just want to criticize things. Yeah. Innately? Yeah. But then on the other side, your guiding light in the early days is what are customers saying about this product? Yeah, what is your feedback? How do you differentiate between all this, this person is just a hater versus this person is just trying to help make the product better? Well, look, I think if you’re in a customer

meeting, they took the meeting for a reason. Yeah. Either they took it because, you know, you’ve got a friend that they respect, and that person respects you. And, you know, they want to hear what you have to say about something that’s important to them, they’re sitting in a seat where they, you know, you know, one, they’ll lay out with their strategic initiatives on what they want to do. And just understanding that is really important. So even if you don’t walk away with great product feedback, you you’re gonna walk away with good industry feedback, you’re going to walk away with perspective on how somebody in your ecosystem perceives this industry, what’s important, what’s not, but you’re walking away from a meeting with somebody who’s got a point of view in a business that you want to be. And so that alone will start to give you a vibe, this is a very big difference when thinking about business and being in business. And it’s like, I’m gonna build a great payment system. That’s really great. That sounds awesome to me with a bank, right? And then let’s come up with a 1000 reasons why you’re not going to build a great payment system. Yeah. But it’s important to get that perspective. I’m not saying don’t do it. For those 1000 reasons. I’m saying it’s really important, though, to get that perspective.

So the vibe, I think, is interesting, right? Because you’ve definitely got a vibe about you, as an entrepreneur, as as an investor, do you think consciously about that the vibe and sort of energy that you have, when you go into a pitch, whether it’s a pitch to a potential teammate, or a potential employee, or it’s a pitch to an investor?

I don’t, because I really, you know, I sell what I believe in, and I’m excited about it for something that I see. And so I think the way it comes off as genuine. And that’s not something I tried to make happen. It’s just something that happens for me. And when I pitched those 1000 vendors at that trade show, not every one of those many conversations was great. Right? But, you know, you start to figure out what works, what doesn’t work, what makes sense, where, you know, I have some ideas, you know, that I think, are really amazing. So a VC was like, Well, what else do you think about this industry? And I’m like, Well, okay, you won’t, you won’t open up that Pandora’s box. Here’s what I think is gonna really happen in like 10 years, and they were like, they would they would just silent. You know, they thought I was crazy. Right after 10 minutes. So you have to learn to when you really want to share everything. And there’s a point of vulnerability in being an entrepreneur, you know, like I look at my business plan as a work of art the same way in music She looks at a song, or an artist looks at a canvas, my business mind is my canvas. And there’s vulnerability when you show it to somebody, and so an artist, some artists don’t want to show all of our, you know, their final, they don’t want to show what they have, we don’t really know that that’s, you know, you’re gonna have an opinion on it. So they want to showcase it a certain way. And you have to learn to do that with a business plan, also, and when you can really be vulnerable with a great investor, is when you can really make progress when you can really kind of get out there and brainstorm on the far out their ideas, and that’s a hard point to get to that chemistry is hard to develop,

is it just come from FaceTime?

For us, I think it’s like in any other relationship, if you’re meeting a new girl, you know, there’s a point of where there’s going to be trust in that relationship where you can open up a little bit more. And I think the same thing holds true in entrepreneurship is a very personal experience. Right? There is some people I’m very constantly Okay, what do you think this idea? Let’s get through this, right? You know, you can do that. Maybe, you know, I have 10 ideas, three are insane. Three, make a lot of sense. And three are terrible. And I don’t know about the last one. But it’s good to be able to develop those kind of relationships over time, but they don’t. They’re far and few between,

who are some of the relationships in your life that have been influential on the guiding lights? I mean, obviously, the customer feedback is a guiding light, but who are your mentors that you’ve had along the way? Is there one that stands out to you as someone that really had a big impact on your career?

No, there’s not, you know, I feel in a, I feel that I work a little bit more in the mental silo than even I would like, but I think it’s, it’s some of my personal circumstances, you know, you know, the way I grew up the way things unfolded in my life, from a personal point of view, you Me, me, the kind of entrepreneur that I am. I mean, I was very much on my own from a very young age. And so there wasn’t somebody I look to for answers many times in my life. And so that’s, that’s part of my wiring, is that I feel like I have things figured out, I know how I want to get there. I know what I want to do. And I know the kind of people I’m wanting to come along for this journey. But there’s not a mentor that I’ve gone to that I would say, This is my go to person for these kinds of things. You know, I feel I hope one day maybe that changes for me, and I hope I can be a good mentor to other people. But no, I don’t have that role in my life.

It’s interesting. Sort of the solitary almost like songwriting, poetry writing. Yeah. And the solitary entrepreneurship is almost like a correlation there. Do you still write poetry or songs? You play music?

I don’t play music. Okay. So, you know, clearly a lyricist. In sixth grade. I was in chorus class. And the teacher I remember her name. I’m not going to say it, but I remember her name. And she said, Oh, hold on, everybody. Quiet. I want just this half of the room to sing. And then she goes, I want to see this road ascending. She goes, she points to me, but I just want you to sing. And she goes, you want to take two gyms? I go, Yeah, I’ll take two gyms and that was the end of my musical career. Yeah, that’s unfortunate. Yeah. So anyway, that was that was my music. That’s my musical career. But I actually think I wouldn’t, I wouldn’t. I would love to learn piano one day, and I actually, I love singing. Everybody loves me singing but I love to sing.

Absolutely. I can relate to that. Man. I can relate to that. So no, no, no, no

musical. Part of my life as of this moment.

Do you listen to music? Yeah. favorite artists?

People are so so it would be up 40 Oh, yeah. Oh, yeah. Cool. Yeah. I love you. I love the music. I love a lot of the story about the music. I love the song higher ground, right? Because it’s about learning. And the key lyric in that song is about the more you learn, the more you realize how little you actually know. It’s a really important lesson. But absolutely,

yeah, absolutely. Well, I’d love to learn. You know, before we wrap here, I’d love to learn a little bit more about the New York’s tech scene, and specifically the enterprise tech scene that you’re so entrenched in tell me about why New York is exciting, an enterprise tech space.

I, you know, I look in New York City as the most natural environment for entrepreneurship to flourish in. Right. It’s a collaborative community, you’ve got to get along with people, right, you know, you can’t cross the street in New York City without dealing with people. And so you develop really great people skills, just living in New York City. The concept of working and living in the same spot, I think, is really important. I think entrepreneurship is a very much a part of your personal life as it is a part of your professional life. I don’t think there’s a big separation. And I think New York City is you know, you’re living and working kind of in the same place. And I think that’s a really important theme. I think this spontaneous interactions you have with people in New York City are really really important. And and communities like workbench, help make those kinds of things happen. More software is sold in New York and anywhere in the world. I didn’t know that stat. Oh, yeah. And between Boston, Philadelphia, New York and DC. I mean, you can sell a lot of software here. And you can develop a lot you can develop software. I mean, the talent nukes has more colleges than any city in the world. Right. And so, you know, people think Boston has so many colleges. It’s a great college town. and colleges overwhelmed Boston. But we have more colleges in New York than we do in Boston. And most people are going to school here. And so because of the buying economics and because of the talent community, those are two big pillars of entrepreneurship. Cornell decided to open up the campus here in New York City. If you’re an ad tech company, you know, you’ve got to be in New York City, if you’re a European tech software company, and you want to come to United States in New York City is the natural place to land and start, it’s better than traveling for more time zones. So you got a lot of Europe and Israel coming here. You’ve got buyers here, you’ve got Stanford of the East being built. You’ve got a collaborative community, that makes sense. You’ve got office space, that makes sense. You’ve got housing for everybody. So yeah, New York’s expensive, but the Bronx costs a lot less. Brooklyn became a viable community. It’s now more expensive than parts of Manhattan, but its addresses the younger person demographic. And so there are a lot of elements in the environment that speak to entrepreneurship just naturally, even if New York City didn’t, even if New York City didn’t have initiatives to support it. I think it just happens here naturally, because of the way the city is built.

You mentioned the expense. Are there other challenges that you see the New York tech ecosystem or the enterprise tech ecosystem needing to overcome? No, it’s really the expense is the is the downside? No,

no, no, it’s I don’t look, I don’t see the expenses, the obstacle, say, Well, you know, salaries are really hard. Like we used to have to compete with investment banks, on Wall Street for great engineers, it’s that’s really reversed now. And if you’ve got a great idea, you can sell some great people on it. You know, they’re not only looking for cash compensation, right? There’s there are multiple forms of compensation. You know, we work has democratized leasing space and made it really easy. And so the costs of getting in business have have dropped. And so I don’t really look at costs as an obstacle to entrepreneurship in New York City at all.

That’s great. Yeah, what what’s getting most of your focus than these days when you’re walking your commute, or, you know, the shower time or the morning coffee time? What’s getting most of your cycles these days?

So look, I’m 46 built a few companies. And I’m dreaming about the years when my daughter goes to college, and my wife and I have a lot of time to, you know, do more things together, you know that that is what I’m personally thinking about, like, alright, I can build one or two more companies, I can invest in, like 30 or 40 more, but then any years, I can, you know, I’ll be in a different mode.

What’s what’s the answer? No, I love the honest answer. That’s that’s exactly what I want, which was fellowship is no easy walk in the park. I’ll tell you that. Definitely not an eight years is it’ll go by like that. But there’s going to be a lot of ups and downs along the way. I’m sure. If, if you’re continuing to be entrepreneurial. Yeah. So what’s at the top of the list for you and your wife, bucket list,

non suburban living. So city country, it’s a GQ into the city now. So my office is is six miles down the road from where I live, which is in what Harbor, New York, and I picked the town that was the first stop on White Harbor, right. So I picked the building in the town, that was the first stop in the town. Because I think commuting sucks. And I wanted to, you know, be with my kids. And by the way, I want my team, you know, now that I’m a little bit older, and I’m working with a lot of the same people over and over again. And they live out in places like this. I want them to build an environment where you know, go coach, soccer, coach baseball, go do your thing during the day, right? Kids come to our office, we give them jobs to do. Right, you know, they’re just as much included in our business as our team is included in their lives. And that’s a really important theme in my life. Now as an entrepreneur, especially given where I’m at with my age, my demographic and my peers. Yeah. So look, you know, there’s no one specific thing I think about it on it consistently on a daily basis. But you know, what I will say is that entrepreneurship is not a career. You can choose, it chooses you, right, and it chose me and I, and I’ve done it, and it’s hard. And so I swear this is my last company, and everybody says, There’s no way but

here’s my wife, and

I gotta just be enjoying the fruits of entrepreneurship.

That’s great. Hopefully get time to take those piano lessons. Yeah, exactly. Well, Jeff, if people want to find you and some of your thoughts on entrepreneurship, how can they find you online?

They can email me. Okay. Yeah. You know, Jeff at Jeff, but I’m not sure what all my stuff is online. But I’ve written things and they are online somewhere. Yeah. So So finally, by the way, I’ve never been a big proponent of promoting myself. Yeah, I think I’m more about the spirit of entrepreneurship and building the business. I am saying Jeff is the greatest entrepreneur in the world. It’s more about the team and the business and the outcome.

Well, I appreciate you taking the time to share your experience and expertise, because there’s a lot of entrepreneurs listening, and I speak for them when I say thank you for sharing your experience.

Awesome. Thank you for the opportunity to connect, of course.

Thanks, Jeff. Hey, Matt Hunckler here again. And that’s it for our conversation with Jeff Leventhal. I hope you enjoyed it as much as I did. I really love his perspective. And just the way he’s tell stories is great, and it makes me went up my storytelling game, but let me know what you learned. Hit me up on Twitter on Instagram. Of course we’ll be publishing a lot of the quotes and extra bonus materials on all the socials. So make sure you give us a follow there. All the show notes are on where you can go to this episode, episode number 23 all of the notes and timestamps so you can go to your favorite juiciest parts of this conversation. Thanks so much for tuning in.