#154 - Building Twice: Jesse Lipson on Scaling ShareFile, Selling for $93M, and Starting Levitate

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There's no formula for being an entrepreneur.

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there was, if there was a playbook, like it would be a lot easier than it is.

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We're training

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Welcome back to another moment session episode of the necessary entrepreneur.

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We have a brilliant mind with us today.

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We just talked for 10 or 15 minutes off camera about where he came from and born and Duke
university and building companies and selling companies.

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So I don't know how much we'll dig into that, but we're going to dig into
entrepreneurship, helping entrepreneurs scale their businesses.

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But let's get to tell you who's going to be on today.

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So Jesse Lipson, he's the founder and CEO of levitate.

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which is operating now.

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It's a fast growing platform that helps service businesses stay top of mind with clients
through authentic relationships.

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We'll touch about the authentic piece here as it goes on.

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But Jesse founded and built Sharefile, which he sold to Citrix and has since launched
Levitate, scaling it from zero into a high growth software company serving thousands of

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businesses.

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In this conversation, I hope to dig in how you scale a service business with software,
Sass.

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how to keep relationships genuine at scale and what founder lessons apply when you've
already exed and starting fresh.

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And what'll come from that is why the heck are you doing it again?

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there's the laugh.

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So, Hey, welcome Jesse.

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Thanks for coming on, So why the heck do you want to do this again, man?

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You hit some home runs and things are good and life is good and you got the curls and the
glasses and you know, you can wear the t-shirt to work.

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Why do you want to do this again?

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I don't know if you've heard of the concept in movies where you need the temporary
suspension of disbelief.

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You know, kind of have to in order to get in and watch a movie.

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I feel like one of the aspects of being an entrepreneur is you have to this weird mix of
taking a crazy risk and jumping into something that you probably shouldn't.

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And then on the flip side, having enough skills to be able to manage that risk.

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And so I think about like somebody like a people that do um

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like climbing mountains or whatever, know, the climb is like steep cliffs.

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People that do those like death defying things.

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You need to be crazy enough to jump in and do it, but then you need to be careful enough
once you do it to like not die.

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And, and I think that's one of the aspects of being an entrepreneur.

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And so like when I jumped into levitate, mean, the main reason was I felt like I was 39
years old.

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I felt like I was too young to retire.

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I was a,

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executive at a public company at Citrix.

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I was reporting to the CEO.

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I decided I didn't want to do that anymore after traveling 75 % of the time, being in kind
of another cheap hotel in South Florida.

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Like, hey, I don't need to do this.

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I sold my company.

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I'm not, you know, it's not really what I want to do with my life.

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And so I felt like, well, I can't retire.

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So I'm probably too young to retire.

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Don't want to be a public company exec.

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So what do I want to do?

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I don't want to be a VC.

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I'd like being an entrepreneur last time the share file.

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So like kind of process of elimination.

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Let me do another company.

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And then, of course, once I got into it, probably for the first couple of years, I was
like, why on earth did I get back into starting another company?

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Like.

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It's it's so hard, it's so hard and actually doesn't really get any easier the second
time.

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And I think the other thing about being an entrepreneur is, or at least for me, I always
find a way to make the stakes really high for what I'm doing.

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So it's like, yeah, even though I had a good exit before, I didn't really need the money.

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I was like, man, if I fail, do this levitate and it fails, then everyone's just going to
think I was lucky with ShareFile.

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I got all these former employees that believed in me to join.

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So, you know, basically convinced myself that

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Um, like I was super dumb decision to start this now that I'm in it.

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If I fail, I'll like ruin my reputation and like, that's kinda, I don't know.

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That's the bizarre psychology.

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I think sometimes it makes entrepreneurs successful is you gotta, you gotta convince
yourself like why you should be doing it.

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If you're just like, Hey, I'm, you know, I'm rich.

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I'm doing it for a second time.

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It's probably just gonna, it's just gonna fail.

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going to fail.

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Yeah.

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You're going to spend too much time on the beach or flying somewhere private or, you know,
sipping, sipping, whatever you want to sip at noon.

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So, um, you said it never gets easier.

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Entrepreneurship.

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Why?

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Yeah, I think, I mean, first of all, I really do think being an entrepreneur, there's a
reason that a lot of the highest net worth um people are entrepreneurs, because I think

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it's one of the hardest jobs.

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It's kind of like the Navy seal of business.

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Getting something off the ground and working is just so hard.

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And I think the early stage of building a company, there's kind of like the

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They call it product market fit.

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Like you start with an idea and then getting something that like customers want to buy.

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They love it.

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They come back and work with you again.

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Or if you're a software company, they stay with you.

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don't, they don't churn and cancel.

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It's so unique.

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Like that, that kind of zero to one is, um, it's hard to replicate that.

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It's not like a formula.

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If it was a formula,

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It would be, you wouldn't get rewarded so much financially for building a business and
making it successful.

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It's like the product of the exact market that you're in, the time in the world that
you're in, how everything else has changed.

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so like I started ShareFile at the end of 2005, early 2006 and going through the financial
crisis, working with a very different employment market, a very different software market

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where Google AdWords was just completely new.

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And I could, I could acquire customers through AdWords and recover the costs before my
credit card bill was even due.

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And then moving into, you know, starting, I would say in 2017, working with Gen Z
employees, going through COVID, the software world is completely different.

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It's very saturated.

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Everything is different.

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And so, um, it's like, doing it again is there's some aspects of it that are easier.

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That beginning phase actually isn't easier.

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Some of the scaling, like I have done some things before and so I've learned and gotten
older and whatever.

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But on the other side, the expectations are higher, you know, the second time around.

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if you just like, you know, if I did share file and I built it to 10 people and sold it
for 10 million bucks, I would have been really thrilled.

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I'm gonna tell you, everyone's like, well, you built share file and it got to the size.

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You need to go that much bigger in order for it to be considered a success.

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Yeah, if it's not some billion dollar valuation now in the marketplace, right?

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How we're being judged is like, are you even doing?

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Yeah, exactly.

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Yeah.

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Do you feel that pressure of that?

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I mean, I'm not saying we should because the challenge is, is we're not trying to, what do
they say that, comparisons, the thief of joy, whether it's true or not, but it's like,

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Hey, make it a billion dollar valuation if you can, if the product market fit matches, but
do you feel the pressure of that obligation sense of responsibility, the outside judgment?

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do.

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Yeah.

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You know, I mean, I want our employees to feel like betting on the company was a good move
and I want our this time.

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So share file, we're bootstrapped.

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um But levitate, we've raised venture capital.

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And so I want them to feel like they're happy that they bet on on our company and they're
happy they bet on me and they got it was a great investment for them.

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And I felt the same way when Citrix acquired us.

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I was like, I want them to feel like this is a good acquisition.

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I don't want to, you know, some people may like, hey, like I got this really great deal
and then the company went to zero.

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Well, the acquire that's kind of on them.

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I guess my nature is just like, always want whoever does business with me to feel like
really happy that it was a good decision.

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And so, you know, I do feel, feel that pressure.

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Where'd that come from, that sense of obligation?

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I really don't know.

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It's a good question.

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I guess like, you know, we talked about a little bit before the show, but my background is
not in business.

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I was, I thought I was going to be a physics professor and I, you know, I got a degree in
philosophy and I thought I was going to be a professor.

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And so, um, I think that I'm like, for me, um, entrepreneurship is more, it's more about

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kind of a creative outlet and the joy of building things.

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And so I think that I probably think about business a little bit differently maybe than
somebody who went to business school.

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Most of what I had done in business is self-taught.

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I mean, I coded ShareFile, but I'm a self-taught software developer.

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I just learned on Google.

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And everything I learned on business is just doing it.

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And a lot of times,

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Being a philosophy major, I guess I kind of looked at a lot of things through first
principles of rather than, this is how you should do things.

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just thought about this is kind of what makes sense to me.

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Um, a lot of times I eventually learned why people say that you should do things a certain
way.

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Cause most of the time when I would, you know, I came up with all these ideas and like,
and my, our first, my first company was a web development company and we decided to move

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the whole company to, uh, um,

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the beach in Florida for a month and you know, it was.

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And so I was like, okay, well, guess that's why companies don't like move everybody to
the, we're like, Hey, well, good.

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you know, it's cool.

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Like we can work from there for the, for a month and then like it will cost that much.

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And then like, okay, that's why like companies don't do that.

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A lot of the times I eventually learn, you know, there's lessons, but I think, um, I
really probably tend to try it.

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I mean, and now I'm laundering my career and I've, I've, I've got a lot of hard, hard won
lessons, but.

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I think I always thought about stuff from first principles and more so than, you know,
from what I learned in business school, which I didn't go to business schools.

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Are you still having as much fun now or less than when you first started teaching yourself
coding?

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I would say I'm having more fun than ever now and I'm back to coding again.

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So with AI, I've been playing around with AI coding assistance and stuff for the last year
and actually having a lot of uh fun with that.

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um So I like building things and um so to me coding is fun, but also if we test something
on the marketing side or on the sales side, we try to be really creative.

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um

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and with what we test.

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uh so like anytime I'm doing creative problem solving is where I'm enjoying myself the
most.

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You talked about first principles and a product market fit and those kind of those in my
mind, those tie together because you got to have them both.

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Yeah.

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So I'm thinking when you started levitate, were you inspired to start this company for a
reason or did you look at the market and say, I'm going to start another company.

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Let me go into the market and see what, what would work, what type of business, what type
of product market fit, not necessarily something I'm passionate about.

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What company would roll and scale and do great.

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Now, is that how you decided?

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settled on Levitate.

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It was a combination of both.

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And I'll tell you a little bit about kind of how it all went down.

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So I've always been an entrepreneur who had a lot of ideas.

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So I've never had a shortage.

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And when I was at Citrix, I was like, I would just have a notebook and come up with a
business idea, write it down, you know, um and know that I wasn't going to, I wasn't going

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to do anything at that point.

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So when I finally kind of started to start my own company again, I had a bunch of ideas.

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For Levitate, one of the things, there were a couple things swirling around in my mind.

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One was at ShareFile, one of the most successful things we did was we had this Microsoft
Outlook plugin.

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What we realized is we were, we realized that if we made it super easy for people to
exchange files, we, and there's a paperclip in Microsoft Outlook where you attach files.

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We created like a secure paper clip.

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You just click this green paper clip instead of the other one and we'll take care of all
the security.

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And we are out the plugin.

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Like was better than Dropbox and Box.

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And even up until a few years ago, if you Google Outlook plugin, ShareFile would come up
like above even Salesforce.

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So one of the lessons to me is like people love to live in their email and calendar.

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And if you can figure out how to tie into the core, you know, email and calendar that
that's important.

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And so actually back in 2017, I was thinking about AI and like, how do you use AI tie into
people's email and calendar to kind of really do some magical things?

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And we were called levitate.ai back then in 2017 when I started the business.

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And the other piece was my wife had a marketing agency kind of consulting firm and she had
about

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40 or 50 people.

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And I noticed that um how she was doing business, would, she would pay a lot of money, a
few thousand dollars a month for Salesforce and email marketing automation.

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But most of the new business she generated came completely outside of those systems.

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She just would do a really good job keeping in touch with people in her network.

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And she kept an Evernote notebook and be like, Mark, you know, I know Mark and he told me,
you know, uh

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whatever he lived in uh Cedar Rapids or Coralville, Iowa for a while.

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he, you know, lives in Cincinnati and, know, she would keep key facts about people.

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And then when she's going to Cincinnati, she'd be like, Hey, who's my Cincinnati people?

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Let me like call Mark and did a really good job of just cultivating those relationships.

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And a lot of her new business came from keeping in touch in just a personal, authentic way
with her network, which is really hard.

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like I think a lot it resonates with a lot of people.

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A lot of us are in this business like law firms, accounting firms, real estate, uh you
your real estate where it's word of mouth referral.

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It's about keeping in touch.

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And all of the software that I saw out there was about kind of just like either spamming
people with automated drip stuff that doesn't deepen the relationship or uh CRM systems

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that are about like moving people through a sales pipeline.

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which in a lot of relationship based businesses is not how you think about the world.

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You just think like, hey, if I keep in touch with good people and they know I'm here and
I, you know, add value, then like good things happen.

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But how do you kind of scale that personal authentic outreach?

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And so um that was what ultimately caused me to um land on Levitate.

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But what I decided to do is,

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I did some interviews with small businesses and I decided not to tell them what my idea
was.

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Instead, I said I would go to lunch with them or something and just say, tell me what your
top three pain points are, like that you think would be most helpful for your business.

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And then I wanted to see whether what I was talking about made their list without me
prompting them.

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And it was kind of interesting.

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00:16:36,828 --> 00:16:40,581
I heard a couple of things multiple times and I was like, that might be a good business
idea.

204
00:16:40,581 --> 00:16:42,902
Like one of them I heard a lot was,

205
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uh, from service businesses was like collecting invoices, you know, it seemed to be a pain
point that a lot of people had.

206
00:16:50,130 --> 00:16:51,406
Cause I was maybe I should do that.

207
00:16:51,406 --> 00:17:03,395
But I still, uh, I heard from, uh from multiple people, this, this whole challenge of
like, want to, I do need to do a better job keeping in touch with my clients, my business

208
00:17:03,395 --> 00:17:05,366
network, you know, that kind of thing.

209
00:17:05,366 --> 00:17:11,170
So, yeah, so I felt like, yeah, I heard the pain point.

210
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without prompting them.

211
00:17:12,210 --> 00:17:18,383
think one of the tough things as an entrepreneur is when you have a new idea is you're
like, I've got this idea.

212
00:17:18,383 --> 00:17:23,882
It's like, you know, you know, recyclable, whatever pens.

213
00:17:23,882 --> 00:17:26,976
I'm just, staring at a dry erase marker.

214
00:17:28,097 --> 00:17:38,842
And then the person who hears your idea, like socially, they don't really, they're, have a
lot of incentives against saying like, you know what, Mark, I really don't think that's a

215
00:17:38,842 --> 00:17:39,800
good idea.

216
00:17:39,800 --> 00:17:41,611
So most people will be like, yeah, that's cool.

217
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Like recyclable dry erase markers.

218
00:17:44,832 --> 00:17:47,613
like the environment is really big and that sounds good.

219
00:17:47,613 --> 00:17:57,737
And so um that's one of the tough things when you're in the idea phase is actually getting
honest feedback and it's not until you start to ask for money and sell that you start to

220
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get true market feedback.

221
00:17:59,658 --> 00:18:08,322
So I try to stay away from that by not telling my idea and actually just asking them what
their pain points were and see if Levitate made the list.

222
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m

223
00:18:09,710 --> 00:18:11,430
And it's, was that 2017?

224
00:18:11,430 --> 00:18:14,254
You're probably doing that in 16 and 17 and.

225
00:18:14,254 --> 00:18:17,670
Yeah, 2017 was basically when I was.

226
00:18:18,478 --> 00:18:21,750
So this is the past eight years, um everything changes.

227
00:18:21,750 --> 00:18:26,702
Like you said, we were COVID and different types of employees and different work methods.

228
00:18:26,702 --> 00:18:29,924
Has the business had to change and evolve?

229
00:18:30,625 --> 00:18:33,862
Is it different than what it started as in 2017?

230
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It is.

231
00:18:35,954 --> 00:18:40,134
And then in some ways it's starting to come back to some of the original principles.

232
00:18:40,134 --> 00:18:42,514
I'll kind of talk a little bit about that.

233
00:18:42,514 --> 00:18:46,774
But, you know, back in 2017, I was like, you know, talk about that.

234
00:18:46,774 --> 00:18:56,594
Hey, can I use AI to help people keep in touch more authentically by like going through
their email, reminding them of the people that they have met with in the past, but they

235
00:18:56,594 --> 00:19:02,892
have lapsed, you know, or they've maybe emailed in the past, they've lapsed, making it
easy to kind of tag people with like a tag.

236
00:19:02,892 --> 00:19:08,203
you with like Cincinnati or if it's a sports team you like or golf or something like that.

237
00:19:08,203 --> 00:19:12,345
And then I can have a really easy way to record some key facts.

238
00:19:12,345 --> 00:19:16,526
That way can say, Hey, you said you wanted to you tag Mark as entrepreneur.

239
00:19:16,726 --> 00:19:21,667
You said that you wanted to keep in touch with all your entrepreneur people at least every
six months.

240
00:19:21,667 --> 00:19:32,814
Here's Mark and like five other people that you haven't kept in touch with and, you know,
reach out or um like, uh let's say you're a Bengals fan or whatever.

241
00:19:32,814 --> 00:19:36,974
And I tagged you with bangles and then bangles win a game.

242
00:19:36,974 --> 00:19:38,474
I can like, who are all my bangles people?

243
00:19:38,474 --> 00:19:41,394
Let me grab those and send out a note to those 20 people.

244
00:19:41,394 --> 00:19:44,614
And I can maybe spend a minute and customize each each one.

245
00:19:44,614 --> 00:19:46,254
So that was the idea.

246
00:19:46,374 --> 00:19:49,714
And my hope was that AI could could help with it.

247
00:19:49,714 --> 00:19:55,114
Unfortunately, back then, AI was not as far along as as where it is today.

248
00:19:55,114 --> 00:19:59,214
And so really, we weren't able to use AI much at all.

249
00:19:59,214 --> 00:20:01,554
So what I found is that we

250
00:20:01,794 --> 00:20:03,785
The value proposition really resonated.

251
00:20:03,785 --> 00:20:06,638
If I talked to like an insurance agent, they're like, you're right.

252
00:20:06,638 --> 00:20:09,380
It's all about keeping in touch, authentic outreach.

253
00:20:09,380 --> 00:20:12,072
I know I don't do as good of a job of that as I should.

254
00:20:12,072 --> 00:20:14,835
And I know that like, that's the most important thing in my business.

255
00:20:14,835 --> 00:20:21,680
So they would buy our product, but then they would cancel after a few months.

256
00:20:21,680 --> 00:20:23,702
So we'd be like, Hey, you know what happened?

257
00:20:23,702 --> 00:20:27,744
And they'd be like, I still totally believe in what you're saying.

258
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It's just, I'm too busy.

259
00:20:29,456 --> 00:20:31,918
And so I realized at the time that

260
00:20:32,758 --> 00:20:38,272
our product was kind of like the workout plan for your business where it's like something
that you know you should be doing.

261
00:20:38,272 --> 00:20:48,188
It's good for you in the long term, but like that's why, you know, gyms have a good
business model is a lot of people buy the membership and don't and don't go do it.

262
00:20:48,188 --> 00:20:56,114
And so what we realized is we actually need to help them write the content and be like a
ghostwriter for them.

263
00:20:56,114 --> 00:20:56,954
Yep.

264
00:20:57,158 --> 00:21:03,183
The challenge for our salespeople, even in this sales game we're in, sales is just human
interaction.

265
00:21:03,764 --> 00:21:05,325
Sales is showing people your value.

266
00:21:05,325 --> 00:21:07,138
Like that's sales 101.

267
00:21:07,287 --> 00:21:09,119
And too many people want to turn into a salesman.

268
00:21:09,119 --> 00:21:10,019
No, just provide value.

269
00:21:10,019 --> 00:21:15,124
But the challenge is in the beginning, it's all business development, new salesperson, new
business.

270
00:21:15,124 --> 00:21:16,075
So that's all you're doing.

271
00:21:16,075 --> 00:21:17,836
And then you start doing the business though.

272
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And then you don't have enough time to do more business development.

273
00:21:19,868 --> 00:21:21,218
That's what we're talking about.

274
00:21:22,040 --> 00:21:24,866
And so how can you help the professionals in business?

275
00:21:24,866 --> 00:21:27,804
continue to run that in the background so we can keep scaling.

276
00:21:27,905 --> 00:21:28,795
Exactly.

277
00:21:29,356 --> 00:21:31,498
The, it is the challenge.

278
00:21:31,498 --> 00:21:35,934
And what happens is we find in newer businesses that I'm around and been a part of.

279
00:21:35,934 --> 00:21:42,431
And when you start integrating salespeople, they'll, it'll, it'll do this because they'll
have this huge ramp up in business.

280
00:21:42,431 --> 00:21:44,203
They'll stop business development.

281
00:21:44,203 --> 00:21:46,825
Their pipeline gets empty and they have to do it again.

282
00:21:47,186 --> 00:21:51,210
So if your system just helps us do this nonstop or we can do the business.

283
00:21:51,854 --> 00:21:53,294
Exactly, exactly.

284
00:21:53,294 --> 00:22:06,854
then, sorry, the reason that it's coming back around is that with AI capabilities, some of
the original things that I envision are getting easier.

285
00:22:07,294 --> 00:22:15,514
So some of the things that we're starting to roll out are now you can actually have a
conversation with your system and I can say, like,

286
00:22:17,390 --> 00:22:23,034
Hey, like, can you find me my, we're going to be raising around a funding.

287
00:22:23,514 --> 00:22:32,911
Can you go look through my contacts or venture capitalists and tell me if it's this check
size, who are the ones that I should be reaching out to and why?

288
00:22:32,911 --> 00:22:45,752
And then the system is able to go find that also do searching on the web and come back and
be like, you should talk to Alison because you know, met with her back in 2020 and

289
00:22:45,752 --> 00:22:50,444
to and she said this and you should talk to this person and that person.

290
00:22:50,644 --> 00:22:52,945
And then same idea is like.

291
00:22:53,485 --> 00:22:55,506
I can just dump some notes.

292
00:22:55,506 --> 00:22:58,448
I talk, I met with Mark and I said, you know, rattle off.

293
00:22:58,448 --> 00:23:05,302
He said he's going on vacation to Bali next month and his wife's name is Susan and you
know, whatever.

294
00:23:05,302 --> 00:23:10,953
And then the system can be like, all right, I'm going to automatically pull out his wife's
name as a key fact.

295
00:23:11,293 --> 00:23:13,324
I'm going to tag him with Cincinnati.

296
00:23:13,324 --> 00:23:24,201
And since he mentioned in his conversation that he's going to Bali next month, do you want
me to put an action item on your calendar to reach out to him in December and check in and

297
00:23:24,201 --> 00:23:26,303
see how the trip was?

298
00:23:26,303 --> 00:23:40,993
so it's able to kind of the technology is finally getting to where we can achieve that
vision for these small businesses is like truly being able to, it's just, um, doing all

299
00:23:40,993 --> 00:23:43,340
that stuff and logging in as CRM is like,

300
00:23:43,340 --> 00:23:44,951
Only 1 % of people can do that.

301
00:23:44,951 --> 00:23:46,932
just, it takes incredible discipline.

302
00:23:46,932 --> 00:23:52,206
And my goal originally was to try to bring that to, bring that to everybody with AI.

303
00:23:52,206 --> 00:23:55,538
And now um we're starting to be able to do that.

304
00:23:55,758 --> 00:23:55,918
Yeah.

305
00:23:55,918 --> 00:24:04,498
I mean, isn't the challenge for stuff like you mentioned Salesforce before and 11, the
challenges is to have all the people work in the organization that to adopt the software.

306
00:24:05,178 --> 00:24:05,878
Right.

307
00:24:05,878 --> 00:24:14,978
And not only you have to adopt it, but I'm sitting here saying, man, if, the input is
done, right, the contacts and the information is put in the system, it'll work perfectly.

308
00:24:15,638 --> 00:24:18,998
So then how do you help companies implement that adoption rate on the front end?

309
00:24:18,998 --> 00:24:21,510
Cause that's what the success is going to be determined by.

310
00:24:21,602 --> 00:24:27,124
And that's what I found is that with, um, relationship based businesses.

311
00:24:27,124 --> 00:24:37,188
like, you know, let's say it's called like real estate, um, law, accounting, wealth
management, big part of the economy.

312
00:24:37,188 --> 00:24:42,206
It's different because first of all, they're mostly referral and word of mouth.

313
00:24:42,206 --> 00:24:45,552
So you don't have to be rigorous about using a system.

314
00:24:45,692 --> 00:24:49,934
Second of all, they're doing the work in addition to, um, selling.

315
00:24:49,934 --> 00:24:51,074
And so.

316
00:24:51,298 --> 00:24:58,540
Like if you're a lawyer, um what's the likelihood you're going to spend a bunch of time
managing your CRM system?

317
00:24:58,540 --> 00:25:01,901
Like you want to be working on billing hours.

318
00:25:02,001 --> 00:25:13,914
And so that group in particular, think is one that if you don't do something completely
different and make it easy for them to keep in touch, they won't adopt it.

319
00:25:13,914 --> 00:25:16,815
Whereas, you know, my company, Levitate, we're a software company.

320
00:25:16,815 --> 00:25:19,406
We've got, you know, over a hundred salespeople.

321
00:25:19,406 --> 00:25:20,506
And so

322
00:25:20,568 --> 00:25:23,461
their job is to be in the CRM.

323
00:25:23,461 --> 00:25:27,684
If they don't put the stuff in the CRM, then they don't have a job.

324
00:25:27,684 --> 00:25:38,534
It's easy in that case to get somebody to use a HubSpot or Salesforce, but if you're a
wealth advisor, if you're a lawyer, unless it's providing you a lot of ROI, you're not

325
00:25:38,534 --> 00:25:42,857
gonna spend an hour typing a bunch of stuff in every day.

326
00:25:43,534 --> 00:25:47,194
It could, what I found in this business, mean, all businesses are sales.

327
00:25:47,194 --> 00:25:47,434
I don't care.

328
00:25:47,434 --> 00:25:48,834
Everybody says it is.

329
00:25:48,834 --> 00:25:52,074
You have to attract and get awareness to think about the thing you're trying to do.

330
00:25:52,074 --> 00:26:05,214
And so, um, what you're talking about, we always talk this three X and five X and 10 X,
but the future success of a sales organization is continuing to nurture all the past

331
00:26:05,214 --> 00:26:10,154
clients and their networks in a hundred percent is there's such a strong capture
likelihood there.

332
00:26:10,154 --> 00:26:11,774
That's not cold anymore.

333
00:26:12,000 --> 00:26:22,542
And cause what we teach people to do without this is, know, whether it's on LinkedIn,
whether you're on Facebook, Instagram, Tik Tok, if it's a business development day, go

334
00:26:22,542 --> 00:26:30,651
into your networks, find something that's important to that person right now, something
they're doing and send them a video, highlight it and talking about it.

335
00:26:30,651 --> 00:26:34,034
That's what you're talking about with, with your company, with the software.

336
00:26:34,252 --> 00:26:34,862
Yeah.

337
00:26:34,862 --> 00:26:35,152
Right.

338
00:26:35,152 --> 00:26:35,342
Yeah.

339
00:26:35,342 --> 00:26:40,945
think that kind of the idea is cold contacting people is just so hard.

340
00:26:40,945 --> 00:26:50,789
Um, and people have a, they have walls up, you know, when it comes to cold contact, but
you actually, and then you have your close friends and you know, those are maybe a five or

341
00:26:50,789 --> 00:26:52,629
10 and you keep in touch with them.

342
00:26:52,670 --> 00:27:03,490
But there's a big group of like, in the, in the several hundred people that you have made
a contact with, maybe you had a good conversation at a conference, maybe.

343
00:27:03,490 --> 00:27:05,631
You used to work with them at your previous job.

344
00:27:05,631 --> 00:27:08,872
Maybe you went to school together, high school, college.

345
00:27:08,872 --> 00:27:11,894
Maybe you went to, you go to church together, whatever.

346
00:27:11,894 --> 00:27:24,319
Where if you just are kind of that thoughtful person that occasionally, you know, reaches
out every six months or year, and when you don't need something, then um you have this, uh

347
00:27:24,319 --> 00:27:29,111
this huge network that they think of you first when they need something.

348
00:27:29,111 --> 00:27:32,502
Or eventually if you've provided value over time,

349
00:27:32,558 --> 00:27:37,678
Um, then it is time for you to ask for a favor that they don't feel like, Oh, this
person's just using me.

350
00:27:37,678 --> 00:27:42,158
I've never this guy from like my high school, all of sudden they want to sell me
insurance.

351
00:27:42,158 --> 00:27:45,938
I haven't heard from them in 15 years and they're calling me about, about insurance.

352
00:27:45,938 --> 00:27:47,498
Like that doesn't work.

353
00:27:47,498 --> 00:27:50,978
And so, um, I a hundred percent agree.

354
00:27:50,978 --> 00:28:02,282
It's this, there's this group of kind of coldish warm contacts that may be in the, you
might have 500 to 2000 of them that if you can keep those warm and

355
00:28:02,282 --> 00:28:05,830
and strengthen those, that's where the real power comes.

356
00:28:06,506 --> 00:28:06,946
100%.

357
00:28:06,946 --> 00:28:10,686
Um, the, what have you learned to go a different direction?

358
00:28:10,686 --> 00:28:15,966
sit here, this software, you guys find a way to integrate this, the way we're sitting here
talking about me.

359
00:28:15,966 --> 00:28:22,606
You've already had, you have thousands of customers, but if you do it in the probably the
right time span, because everything, right?

360
00:28:22,606 --> 00:28:27,606
We all have these at some point in three or four or five years, something maybe it's not
relevant anymore.

361
00:28:27,606 --> 00:28:28,086
Right.

362
00:28:28,086 --> 00:28:29,126
So you do that.

363
00:28:29,126 --> 00:28:30,606
I'm sure it's a billion dollar thing.

364
00:28:30,606 --> 00:28:35,326
If you can really tweak this and it's, I see it from running my company.

365
00:28:35,822 --> 00:28:42,408
Um, but if we go back to your entrepreneurial days, talked about in the beginning, it's
like, why did I do it again?

366
00:28:42,408 --> 00:28:43,228
And it's crazy.

367
00:28:43,228 --> 00:28:44,149
And it's insane.

368
00:28:44,149 --> 00:28:49,713
Um, what are you using now as the not 50 yet?

369
00:28:51,375 --> 00:28:53,316
What are you using now?

370
00:28:54,338 --> 00:29:04,896
That back then you had no clue about, about your brain power, your intelligence, your
knowledge, because you were a highly educated mind in your twenties and thirties.

371
00:29:05,932 --> 00:29:08,073
It's almost like you would be a different writer now.

372
00:29:08,073 --> 00:29:11,605
If you were an author back then, you would have evolved to a new type of author.

373
00:29:12,165 --> 00:29:14,516
So what are you still using?

374
00:29:14,516 --> 00:29:25,832
And then the same conversation, what are you using now in your brain power and how you're
seeing business that you had no clue about in operating the business to give the old,

375
00:29:25,832 --> 00:29:29,678
right, Mark and Jesse some tidbits here that whether they listen to or not.

376
00:29:29,678 --> 00:29:30,858
Yeah.

377
00:29:31,358 --> 00:29:33,278
Yeah, it's a good question.

378
00:29:33,338 --> 00:29:37,278
I mean, I think in terms of how I've changed as a.

379
00:29:37,498 --> 00:29:39,278
As a person.

380
00:29:40,238 --> 00:29:46,078
I would say, like, if you if you interviewed me back in 2010 in the early share file days.

381
00:29:47,558 --> 00:29:49,518
I was probably.

382
00:29:50,998 --> 00:29:52,958
A lot more.

383
00:29:53,698 --> 00:29:58,214
Kind of quiet and analytical and operating on.

384
00:29:58,542 --> 00:30:06,242
Even more first principles, just kind of like, it's a little bit easier too in your
bootstrap business, you don't have to answer it to a board of directors.

385
00:30:06,622 --> 00:30:17,322
You know, very principled on the values of the business, kind of how to make decisions, a
little bit more detached from the outcomes.

386
00:30:17,602 --> 00:30:27,942
I would say today, I feel like I am probably

387
00:30:27,970 --> 00:30:35,655
a little bit more intuitive than I was in my earlier career, just because I've been
through so much.

388
00:30:35,655 --> 00:30:50,170
um And the other just skill that I've had to build is um this is something that I like to
talk about when people ask about m leadership and growing as a leader.

389
00:30:50,170 --> 00:30:58,060
I think there's a stereotype of a CEO of like somebody who's, you know,

390
00:30:58,350 --> 00:31:08,324
tall and polished and perfect teeth and they're like Tony Rob and you know people think
about like there's something like that and if I'm a quiet you know person or you know I

391
00:31:08,324 --> 00:31:19,789
have these qualities and maybe I'm not a CEO or a leader and first of all one of the
things I say is I don't think there is a there is a personality type like you can be a

392
00:31:19,789 --> 00:31:28,102
leader no matter whether you're outgoing, social, introverted, uh

393
00:31:28,504 --> 00:31:32,557
professor like and you brilliant or average intelligence.

394
00:31:32,557 --> 00:31:37,921
Like there's all amazing, successful leaders come in like a lot of different flavors.

395
00:31:37,921 --> 00:31:48,479
um And uh the other thing that people miss when it comes to like seeing somebody like if
somebody's looking at this, listen to this podcast and think about, know, this, this guy

396
00:31:48,479 --> 00:31:50,132
like, I've never gone on podcast.

397
00:31:50,132 --> 00:31:55,194
I'm like, you know, this guy, he's obviously a CEO and he's comfortable talking.

398
00:31:55,194 --> 00:31:56,074
Well,

399
00:31:56,428 --> 00:32:10,941
I got that way because I've done it a lot and you over the years and so um I like I'm much
more comfortable like at Citrix I would go in every year in our our customer conference

400
00:32:10,941 --> 00:32:19,429
and do like speak in front of multiple thousands of people and so you just do stuff a lot
and you get and you get used to it and you get comfortable with it and so I think I've

401
00:32:19,429 --> 00:32:23,348
built a lot of those skills with um people.

402
00:32:23,348 --> 00:32:26,542
over the years and those weren't skills that I used to have.

403
00:32:26,542 --> 00:32:30,746
was much more of like a, you know, professor.

404
00:32:30,799 --> 00:32:33,863
Yeah, that's talking about thinking about philosophy.

405
00:32:34,766 --> 00:32:40,184
Yeah, the so do you think so maybe the answer to my long question is like you just have to
go through it.

406
00:32:40,184 --> 00:32:42,848
You just have to go through it to develop the skills.

407
00:32:43,264 --> 00:32:43,764
Exactly.

408
00:32:43,764 --> 00:32:46,175
It's like you become better at what you keep doing.

409
00:32:46,175 --> 00:32:51,458
um so like being an entrepreneur, you build a lot of skills.

410
00:32:51,458 --> 00:32:56,994
And so you see when you see a successful entrepreneur, you see all the skills that they
built.

411
00:32:56,994 --> 00:33:07,074
I would say don't feel disheartened if you're like, well, you know, I'm not good with
words and, like you will become you will become a lot better.

412
00:33:07,074 --> 00:33:11,126
And like, I'm not inclined to, you know,

413
00:33:11,160 --> 00:33:12,961
chop it up with employees or whatever.

414
00:33:12,961 --> 00:33:19,357
But over time, it's like being super busy, would take, I'd be like, I've got 30 seconds in
the cafeteria line.

415
00:33:19,357 --> 00:33:22,689
Like, let me take those 30 seconds and like chat with this person.

416
00:33:22,689 --> 00:33:32,858
And um charisma is almost like a, it's almost like a tool that it's an efficiency tool
that you develop as, you become more successful, which is like, I don't have much time.

417
00:33:32,858 --> 00:33:35,970
Let me like, let me like connect with somebody.

418
00:33:35,970 --> 00:33:36,761
Yeah, exactly.

419
00:33:36,761 --> 00:33:38,272
Let me like chat with this person.

420
00:33:38,272 --> 00:33:40,094
Hey, I'm sitting here for 30 seconds.

421
00:33:40,094 --> 00:33:41,064
Let me like,

422
00:33:41,304 --> 00:33:45,022
talk to this employee and learn about what's going on with them.

423
00:33:45,718 --> 00:33:56,279
What's, um, what's like the big thing quietly over the past two or three months that
you've been dwelling on problem solving on really working through?

424
00:33:56,279 --> 00:33:57,640
What, what is it?

425
00:33:58,124 --> 00:33:58,556
Yeah.

426
00:33:58,556 --> 00:34:01,773
Um, I think the big thing is.

427
00:34:04,411 --> 00:34:09,634
When you compound and growth as a business, the bigger you get, the harder it gets.

428
00:34:09,875 --> 00:34:13,748
And, you know, we're, we have almost 8,000 customers now.

429
00:34:13,748 --> 00:34:28,940
And, and, uh, on the one hand, we see this really big opportunity, which is, feel every
small business, um, has this need to get help with keeping in touch and, um, their social

430
00:34:28,940 --> 00:34:33,518
media and their websites and, um, they don't want to do it themselves.

431
00:34:33,518 --> 00:34:44,738
And, uh, and so I see this gigantic opportunity and that we've in some ways been planning
for since 2017 when we created levitate.ai and now AI is here.

432
00:34:44,998 --> 00:34:54,798
And on the other hand, connecting that to like, well, how do you keep growing 50 % a year
as you start to, we're, we're like 270 employees now.

433
00:34:54,798 --> 00:35:03,532
Um, and so I think, um, connecting those, those dots and figuring out like how to.

434
00:35:03,532 --> 00:35:05,843
how to keep going and how to keep growing.

435
00:35:05,882 --> 00:35:18,733
It really um stretches your mind in terms of like thinking about um like for one example,
we just opened an office in Toronto, Canada, know, which six months ago we would never

436
00:35:18,733 --> 00:35:21,054
have thought to possibly do that.

437
00:35:21,054 --> 00:35:32,322
But it's worth thinking about growing our talent pool and really if you, if you really
stretch and think, all right, let's say in 2030, if we want to be a, you know,

438
00:35:32,322 --> 00:35:39,884
thousand person company, like probably doing what we're doing the way we're doing it won't
get us there.

439
00:35:40,024 --> 00:35:50,147
so we're actually, you caught me like in two weeks where we have a, actually it's just
over a week now, a week and a couple of days, we do like a multi-day senior management

440
00:35:50,147 --> 00:35:51,997
offsite where we talk about this kind of stuff.

441
00:35:51,997 --> 00:36:01,600
And so I've literally been the last few weeks putting together a presentation, thinking
about those kinds of topics of like,

442
00:36:01,664 --> 00:36:11,646
scale and like how do we do things differently as we scale and like if we keep doing what
we're doing it doesn't it's it's not going to keep working.

443
00:36:12,046 --> 00:36:20,298
How do you know as a leader through all these years of experience, how do you know if you
don't have the answers internally, you've mulled over it enough, you need to go outside?

444
00:36:20,302 --> 00:36:23,845
um Yeah.

445
00:36:24,486 --> 00:36:36,567
I try to, I don't know, but I try to always keep in touch with what is happening in the
environment around me.

446
00:36:36,567 --> 00:36:45,025
I think that's one of the important roles of a CEO is to kind of have the most complete
information about the company.

447
00:36:45,025 --> 00:36:47,136
like knowing everything about internal.

448
00:36:47,942 --> 00:36:50,523
knowing what's happening in the external trends.

449
00:36:50,523 --> 00:36:59,327
you know, one way I do that is I do listen to podcasts and I'm on Twitter a lot uh to try
to see, you know, what's what's happening.

450
00:36:59,387 --> 00:37:01,348
And that's that's one data point.

451
00:37:01,348 --> 00:37:10,762
And so I guess going back to something that we were talking about before we started
recording about how there's no formula for being an entrepreneur.

452
00:37:10,762 --> 00:37:15,814
If there was it, if there was a playbook, like it would be a lot easier than it is.

453
00:37:15,968 --> 00:37:24,421
And so to come to an answer, it's kind of like, you have to, feel like always be in touch
with the external perspectives.

454
00:37:24,802 --> 00:37:35,396
Always be in touch with what your customers are saying, what your employees are saying,
what your investors, if you have them, saying, and somehow use all that together to have

455
00:37:35,396 --> 00:37:38,807
the most complete picture and make a decision.

456
00:37:38,868 --> 00:37:45,270
and, and so, and sometimes it's not the right decision, but, uh,

457
00:37:45,922 --> 00:37:56,377
I mean, I wouldn't say I know, but I certainly know when I don't, when I'm, I'm, uh, and I
know when most people know when, when I feel a lot of indecision.

458
00:37:56,377 --> 00:38:03,836
And so that's usually when I start to, you know, ask friends and tap into my external
network on, on some things.

459
00:38:04,534 --> 00:38:07,886
The, um, we get sitting here, man, there's so many different places we could take this.

460
00:38:07,886 --> 00:38:10,378
could talk for two hours, even though we wouldn't do that to each other.

461
00:38:10,378 --> 00:38:14,141
But, um, as, as we bring this to the end, I think there's a ton of value you have.

462
00:38:14,141 --> 00:38:18,734
have this perspective of bootstrapping a business and selling it for.

463
00:38:18,734 --> 00:38:21,296
Yeah, it was 93 million bucks.

464
00:38:21,296 --> 00:38:23,547
say you sold a hundred million dollar company.

465
00:38:23,547 --> 00:38:24,387
Yep.

466
00:38:24,428 --> 00:38:27,880
And then this time around you raise capital.

467
00:38:28,110 --> 00:38:28,966
Yeah.

468
00:38:29,272 --> 00:38:30,513
Can you take a step back?

469
00:38:30,513 --> 00:38:39,097
know you're in it now, so you have to tell all the employees and all your investors, this
is a great move and raising all this, but what advice do you give to people when they're

470
00:38:39,097 --> 00:38:41,848
evaluating both scenarios?

471
00:38:41,848 --> 00:38:48,311
Because this is real world now in this tech environment we're in, there's billion dollar
valuations flying left and right.

472
00:38:48,392 --> 00:38:53,184
So do you bootstrap it or do you raise outside funds?

473
00:38:53,356 --> 00:38:55,667
Yeah, it's a good question.

474
00:38:55,667 --> 00:39:11,183
would say to probably fully answer it, I would also need an hour, but I would say to put
it into one minute that the long version of the answer would be, it actually depends a lot

475
00:39:11,183 --> 00:39:13,774
on what you want out of your life.

476
00:39:14,195 --> 00:39:22,220
Cause sometimes people want to make a huge impact and make a dent in the universe, you
know, and in that case, maybe raising money.

477
00:39:22,220 --> 00:39:24,631
might be the only way to do it or the best way to do it.

478
00:39:24,631 --> 00:39:38,695
um think that ah my step, my advice, if I don't know the person I'm talking to is if you
can bootstrap do, you know, I think that is better for most people.

479
00:39:38,695 --> 00:39:50,698
If, if you're able to do it, I think for levitate, you know, frankly, I invested some
money in the business to see it, see the business and we got to the point after, um,

480
00:39:51,126 --> 00:39:58,128
a year or two where uh I realized how much more I would need to put in to get us to where
we need to be.

481
00:39:58,128 --> 00:40:02,209
And my wife was like, I'm not comfortable with you putting that money in.

482
00:40:02,209 --> 00:40:05,130
And I had, course, like plenty of investors.

483
00:40:05,130 --> 00:40:09,891
When you have a successful outcome, like share file, it is easier to raise money.

484
00:40:09,891 --> 00:40:16,223
I think in my first business share file, even if I would wanted to raise money, if I
decided, Hey, VC is right.

485
00:40:16,223 --> 00:40:18,133
I don't think anyone would have given me money.

486
00:40:18,133 --> 00:40:20,364
Like I didn't have any credibility.

487
00:40:20,364 --> 00:40:21,134
was

488
00:40:22,779 --> 00:40:26,962
I started my first business a year out of college as a website company.

489
00:40:26,962 --> 00:40:34,009
um I could have tried all I wanted, but I don't think anyone would have given me VC money.

490
00:40:34,009 --> 00:40:39,513
Then of course, after ShareFile, everyone would have given me VC money because I had a
successful business.

491
00:40:39,514 --> 00:40:43,067
I tried to do it actually self-funded for the first couple of years.

492
00:40:43,067 --> 00:40:49,322
Then my wife threw the flag and said, no, we don't want put any more in.

493
00:40:49,742 --> 00:40:53,546
Of course we have put a lot more in since then, we also have investors.

494
00:40:53,546 --> 00:40:59,712
yeah, mean, cold advice, would say, bootstrap if you can.

495
00:40:59,712 --> 00:41:05,338
There's a lot of complexities to being in the VC world and it puts you on a certain track.

496
00:41:05,338 --> 00:41:08,461
And when you're on that track, you can't really get off that track.

497
00:41:08,461 --> 00:41:09,858
uh

498
00:41:09,858 --> 00:41:11,370
They'll get you off of it, right?

499
00:41:11,370 --> 00:41:13,134
that doesn't stand on it.

500
00:41:13,134 --> 00:41:19,525
If you get off the track, you're going to suffer severe bodily injuries by getting off the
track at that speed.

501
00:41:19,988 --> 00:41:25,938
So you're on it, whereas you have a lot of optionality as a bootstrapped, including the
ability to raise funding later.

502
00:41:26,766 --> 00:41:28,553
So bootstrap it if you can.

503
00:41:28,974 --> 00:41:31,110
I would say, I would say so.

504
00:41:31,190 --> 00:41:36,492
And if you're going to be an entrepreneur, you better tell yourself you can, because
you're going to tell yourself you can in a lot of different avenues.

505
00:41:36,492 --> 00:41:39,503
um Hey, thanks, man.

506
00:41:39,503 --> 00:41:47,276
We'll give you all the highlights to, to levitate and all that, but where, where
personally, where's the place that people can engage with you mentioned X you have your

507
00:41:47,276 --> 00:41:47,797
link.

508
00:41:47,797 --> 00:41:48,917
People want to follow you.

509
00:41:48,917 --> 00:41:51,074
What's the personal place they come and follow you.

510
00:41:51,074 --> 00:42:00,620
Yeah, I don't do a lot of I'm more of a lurker on X, you I don't post much, pretty rare,
but but I am there.

511
00:42:00,620 --> 00:42:04,462
Jesse Lipson, J.S.S.E.O.I.P.S.O.N.

512
00:42:04,462 --> 00:42:10,636
and then LinkedIn, you know, uh I'm on I'm not a very prolific poster anywhere.

513
00:42:12,268 --> 00:42:14,699
And I actually, I really enjoyed the conversation today.

514
00:42:14,699 --> 00:42:15,832
I like podcast medium.

515
00:42:15,832 --> 00:42:19,785
It's like, it's good to be able to just chat and talk through stuff.

516
00:42:20,727 --> 00:42:24,430
So I guess, uh, know, tune in.

517
00:42:24,522 --> 00:42:26,046
Use their favorite AI to find you.

518
00:42:26,046 --> 00:42:26,608
Right.

519
00:42:26,608 --> 00:42:34,336
What's, um, which platform do you use any of the three or four perplexity open AI are you,
are you using any of those?

520
00:42:34,668 --> 00:42:40,560
Yeah, I mean, use chat GPT and our company uses open AI for a lot of our tech.

521
00:42:40,560 --> 00:42:52,513
And then personally with the our engineering team and then with coding, I use cloud code
and and I actually been using it even for stuff, not coding like uh brainstorming ideas

522
00:42:52,513 --> 00:42:56,744
for uh for my keynote presentation and stuff like that.

523
00:42:56,744 --> 00:43:04,376
So like that keynote, I brainstorm back and forth with it and then uh had it read me an
outline, had it wrote me a speech.

524
00:43:04,376 --> 00:43:14,287
put it into Google notebook LM, had it do a podcast about about my speech just so could
listen to people talking about my speech and and see like how it was being perceived and

525
00:43:14,287 --> 00:43:16,119
so I could kind of like tweak it.

526
00:43:16,119 --> 00:43:17,800
So those are my main tools.

527
00:43:17,800 --> 00:43:23,496
But cloud code, I've got I've got 10 cloud code windows open on my on my laptop.

528
00:43:24,182 --> 00:43:25,645
We see you working.

529
00:43:25,647 --> 00:43:27,513
Hey, thanks, man.

530
00:43:27,513 --> 00:43:30,862
I hope you have an awesome breakout for your leadership team.

531
00:43:30,862 --> 00:43:32,882
Yeah, thank you, Yeah, I appreciate it.

532
00:43:32,882 --> 00:43:34,286
I really enjoyed the conversation.

533
00:43:34,286 --> 00:43:39,006
Yeah, take your 270 to a thousand and take your 8,000 customers to 100,000, right?

534
00:43:39,288 --> 00:43:40,447
That's the dream.

535
00:43:41,118 --> 00:43:41,830
You can do it, man.

536
00:43:41,830 --> 00:43:42,332
That's awesome.

537
00:43:42,332 --> 00:43:42,703
Thank you.

538
00:43:42,703 --> 00:43:44,066
I'm sure people will follow along.

539
00:43:44,066 --> 00:43:49,952
ah Maybe anytime if you're coming through Cincinnati, we see each other, we could sit down
with official studio.

540
00:43:49,976 --> 00:43:52,029
I will tag you in my Levitate

541
00:43:54,476 --> 00:43:54,908
man.

542
00:43:54,908 --> 00:43:57,214
We'll, uh, we'll, we'll keep on checking in.

543
00:43:57,214 --> 00:43:58,737
Thank you for coming by.

544
00:43:58,739 --> 00:43:59,441
Thanks, Mark.

545
00:43:59,441 --> 00:44:00,262
um