Welcome to the Profit Lead Podcast, where we discover proven growth strategies for bootstrapped entrepreneurs from the people who have done it before to help you accelerate your business. The Profit Lead Podcast is brought to you by EWebinar, the leading automated webinar platform, which could save you from doing the same webinar over and over again, from sales demos to onboarding to training.
EWebinar turns any video into an interactive webinar that you can set on a recurring schedule or make available on demand, which means you can do hundreds of webinars without ever needing to actually be there to host them live. This podcast is a forum for the unsung heroes of SAS, the founders and others behind bootstrapped startups who are creative and resourceful enough to forge a pathway to success.
Here is where they get to share everything they learned along the way, so you can benefit from their experience and find success in your own benders too. Welcome to Profit Lead, the podcast for bootstrapped entrepreneurs looking to make it happen. My name is Melissa Cwan, I'm the co-founder and CEO of EWebinar and your host. My guest today is Lloyd Lowe, co-founder of BOS.AI and Traction. Before we get started, let me give you a quick background on Lloyd's journey.
He's been an entrepreneur for 15 years and is also an angel investor, podcast host and community builder. BOS.AI is a fintime platform that provides businesses with R&D and innovation funding. Lloyd helped BOS.AI to eight figures AR before securing over 100 million in capital. In parallel to BOS.AI, he co-founded in BOS.Traction, a global community of more than 100,000 entrepreneurs and innovators.
Traction conference has consistently been ranked one of the top nine marketing conferences in North America by Inc.com, Forbes and Huffington Post. Three of his BOS.AI and Traction, Lloyd ran product and go to market for a number of early stage startups. Although his specialty is taking companies from zero to one, his purpose and passion in life is to bring people together to create big impact. Above all, Lloyd is a good friend of mine, someone I consider a mentor and a role model.
He's one of my favorite founders in the world, which is why I saved him for the last episode of the season of Profit Lead. I'm not using the word favorite here lightly. He's the ultimate hustler, he's the strongest, kindest and most generous person in my support network of founders. So, I'm stoked to have him here today to talk about exits, cashing out, and the route to wealth and freedom that no one talks about. Hey, Lloyd, how's it going? I'm doing well.
Thank you for that kind intro and the feeling is mutual. Feeling is mutual. You've been my Agnian. Wipping me into shape and giving me the tough love whenever I go astray. So, the feeling is mutual. What's the opposite of Agnian? What's the male version of that? Hmm, what is the male version of that? Let me ask Chad Gbt, what is the male version of Agnian and let's see what it says. Oh, it's thinking. Agnian. It's not that creative. Well, you're my Agnian. Not creative. I'm my opposite.
I don't do that tough love at all. Well, just thought to yourself, we have to do it to each other. Yeah, so thanks so much for coming on the podcast. What drink did you bring with you today? I don't know. I'm pretty boring. I'm trying to drink two liters, three liters of water every day. So, this two liter bottle of water is massive. It's bigger than my face. So, is that like a hell thing? It's not. I forget to drink water.
So, this is, yeah, I guess, get hydrated is one of the health things I guess makes me feel good. Well, you do live in the desert, I guess. Yeah, yeah, definitely. Live in Dubai. Well, I brought this Heineken with me today. It's a bottle, not a can, since I'm an Amsterdam, and this is the local beer, and the Heineken brewery is actually just down the street from me. It is 3 p.m. where I am right now, but I feel like I've earned this.
Since I started this podcast on a whim, I wanted to start this kind of as a creative side project, and here we are on the last episode of this season. So, I'm going to create some ASMR magic and open this in front of Mike with my little dinosaur bottle opener. All right, well, cheers. Cheers, cheers, cheers. Yeah, beer makes me gassy. I think I'm like, mindy gluten intolerant. Well, it's probably good for your health, but it's really good.
So, if you're at home, please join us for this last drink of the season. So, having talked to an interview, thousands of founders by now, how do you think most founders think they'll get rich from their startup? The more founders I talk to, and like you said, interviewed everyone from Jeff Los and Twilio CEO, three there, so host CEO, so like two extremes, one venture backed, and worth north of 10 billion, another completely bootstrapped.
And everyone in between, and the more people I talk to, the common theme is everyone's looking to create some massive impact. And they don't think about money as a means. The common theme is after a couple million, money sees us to have its motivating factor. So what's the greater good that you're trying to create? What's the impact you're trying to leave on the world? What's the legacy you're trying to create? This is the common theme.
Now, it could be that everyone's very PR and PC, and that's what they're saying, but I genuinely feel a lot of them are focused on that impact and could be upbringing, it could be many things. But as you look at these themes, with the Jeff Los and Twilio, he did StubHub before, he did another startup before, and now he's doing Twilio and it's become this massive company. These guys just don't stop, right?
Twilio, first a very good successful private company, it's then when public, they're still going, they're still going, they have a lot of money. Yeah, so there should be something deeper that's motivating them to keep going. I also have a couple of friends that have turned down, exits in the 30 to 50 million range that are life changing amounts of money. And a question I ask is like, hey, why did you turn it down? And they're like, hey, what am I going to do after this?
I'm going to probably end up taking some break and then going and doing another startup and then started ground zero all over again. Why do that? I'm not to nickname it against I'd CEO, right? I mean, they also had a majority exit this soul for a billion to this equity, but he's still CEO. And he said, my previous startup, I think they sold at 20 million ARR or so.
And he's like, I wish I just stuck it out sometimes because now you're at zero and you got to grow it all the way to 10 and that's the hardest part growing at a 1020. Once you're in that 20 million range, then it's a lot of optimization. As a founder CEO, you can flex at different things, right? You can keep reinventing your job in the job per se. You can take on new markets, new channels, et cetera, and keep pushing.
So I think a lot of these people, especially in the venture back, which has been the most of the founders I talk to, they make good salaries once you're at Series B, C, D, right? And they have equity. So why sell if the exit's not obvious, if you can keep going, if I'm going to have to then start all over because that's my DNA or that's what I care about, starting all over and going that journey again, why start from scratch, and especially when the vision is not complete.
So that's what I get for the most. But would you say that for most founders, they're at least for their first startup, they haven't made the 10, 20 million ARR yet. Would you say most founders think they're going to get rich from an exit, like just sell their company? Again, two camps here. It's very hard to pull out the internal truth from venture back founders.
Yeah. I think bootstraff founders are a lot more honest because they have the venture back founders because we've given this story to investors that we don't care what exits, right? If you tell VCs, this is my exit strategy and that exit strategy is anywhere south of a billion or five billion, maybe in this market, 10 billion, then I think you're thinking too small. So a lot of people around this journey saying, my focus is impact, this is how we can be a hundred billion dollar company.
This is how we can, I don't know, kill Apple or Google or whomever the giant in their industry is. And also as a function of being a venture back founder, not in this market in the last two years of the COVID boom, a lot of founders made money. They could take secondaries off the table. Yeah, yeah. But the reality is a lot of founders make decent money post BC freedom plus salary. Of course, not complete freedom when you have a board on your head, but they're doing things they like.
That's where they're sticking around and they have the upside of the equity somewhere along the way, maybe between the B round and the D round, they take some liquidity off the table. So I think it's very hard to pull the truth like, hey, what are you in it for? Some people say, I say upfront, I want to make money, but most venture back founders will say, I'm in it to create this impact and money will come.
I truly believe this actually and maybe it's people's DNA or upbringing that forces in the path of impact. But if you focus on money, you end up making short term decisions. If you focus on control, you destroy relationships. And I've seen this, if you focus on impact, you can build something lasting. But that being said, a lot of the boot shop founders are more honest, right? They'll say straight up. They need to make some money. I'll give you my story, right?
So we bootstrap BOST. Before BOST, Alex and I worked on a couple other companies that didn't work out. We did automatically, which was a chatbot in 2013, built on top of Zendesk. And nobody knew what a chatbot was. This is 2013, imagine. A chat UI on the side of Zendesk. We got 1,000 plus users, but it failed because we can get the tech working. Then I worked on Speakeasy. He was venture back, raised 6 million in an idea. And we died with 10,000 plus users. We could not get the tech to work.
It was an AI-driven sales assistant tied to your phone call. And then we did an events company, which was called Cloud Factory, and the third partner ran away with all the profits we had to sue him. So it was like misery, never making money. His wife is a lawyer. My wife's a doctor. They're running the family. And then BOST, we were running like a consulting firm in parallel to all these projects, these startup hustles. And then we realized, we're doing all this work manually at BOST.
It's a big market. Giving companies aren't even funding. You can create a whole new category because there's all these government tax credits available. But it takes a long time to get the money. It's prone to frustrating audits and it's a cumbersome process. Why not just automate this? Customers are already paying us. Put them on software. And then front load them the cash. And then you get this unique data set of R&D and finances that you can give them insights on how to innovate faster.
And so then we bootstrapped the company because the reality is 99% of the venture back companies fail. After university, I've only ever worked for venture back companies. And BOST was the first bootstrapped outing. And either worked at venture back companies or been on like exact teams or founding teams. And so the reality is you know that venture back companies have like a one in a hundred chance of having a good outcome. And Alex was clear from day one to me. I only care about making money.
He says this to me every single day. I only care about making money. For me though, I think it was my way, were raised or whatever it was. But I, you know, a lot of people say things, but you got to watch their actions. I never thought about money first because I would do stuff for free. I'd go and volunteer. When I wanted to build a network, I'd volunteer everywhere for free, building traction. It made no money for years. So I never thought of that.
And even now, I think when the SVB was going to fall and as a function of it, collateral damage, first republic bank was going to fall. I had a bunch of money sitting in first republic blank that I had logged into for six months. So I don't think money first. And I think it has a lot to do with nurture. But here's the key thing, my key learning, talking to thousands of people, bootstrapped founders, venture back founders on the podcast in person.
The key theme there, and I think why people think different ways is money is just a means to buy freedom. All my life, I chased success looking for happiness. Ultimately realized success finds you if you're in a happy state of mind. And what is success? It's freedom to do what you want, where you want, with whom you want, and when you want. Right? On your time, on your dime, in your prime.
But did you not equate, like you say, you weren't focused on money and Alex was, but did you not equate at that point, money with freedom? Because you must have been so tied to your business at that time. We're so tied to the business, but when you're doing things that are fun, and it's your way of life, like for me, socializing, networking, my entire network, I mean, I run a community attraction. My job was building this community as a function of building both, to drive growth for both.
So never felt like I was selling. It was just networking and my whole entire network and friend circle is that. So it never felt like I was doing a job. It felt like I was building this community and doing things that were fun. It hit me when we sold a majority to a growth equity p firm, and I then, as a function of that, had to step back from the day to day. And when I step back from the day to day, we cashed out, and it's life changing money for me, Alex, right?
Like, I made more money than probably anyone in both sides of my family, my wife, family, or my family. But I got depressed as a function of that. I got depressed because I lost my identity. I was all over the press, TechCrunch, VentureBeat, 50 plus podcasts, Frontline on the community, MC and conferences. I was Mr. Post. I was Mr. Post. I was all about Post. And one day you come back and you lose your identity.
And I came home and I hugged my wife that day and I'm like, listen, I'm really sorry for every time you needed me and I wasn't there. Today, the company doesn't need me and you guys are the only people I have here. But I lost my identity. I got depressed. I got overweight. I started excessively drinking, smoking, part. I just, I lost my way. I face planted. Then one day my wife sees me and she's like, listen, if you kill yourself doing this, I understand you're depressed.
And now you've taken enough time to mop over this. But if you kill yourself, the only people who are going to regret it or feel bad or suffer is your family. Plus, you're not going to do any service to the community. You work so hard to build. So why don't you do something about it? That afternoon I was having lunch with Atlassian's president on new and she told me like, hey, self-care is never selfish. It's the only way you can create value in the world.
She went to Atlassian to resign to the CEO and he said, hey, don't resign. Just take the time you need off. And she took a year off to do like, anime rehabilitation, spent time in Antarctica and Africa and so on. And she came back to become the president of this like $40 billion company. Then I talked to a shrink. I told the shrink like, hey, my life's been like a video game. My wife's a very brilliant dog. She got into med school without MCATs in her second year of undergrad.
Her parents never wanted us to get married. And her mom said like, this guy's never going to amount to anything. And so I went on this 10 year journey like, I'm going to prove this woman wrong. All three of her kids are doctors. And so I did one startup fail, second one fail, third one, somebody ran off with money. So it was the ups and downs, right? So the professional downs, every time you think you have something and it fails, like, you get thousands of users, tech doesn't work.
You do this event. It's successful. It makes the quarter million in profits. But you have the third person who is almost with all the money. In between, we were expecting twins lost a child. All these things, like there's always these ups and downs. But the one other common theme in talking to thousands of entrepreneurs is what I realized is there's this common anger that people have.
This burning anger to prove the naysayers wrong, that changed the status quo, to write a wrong, to do something and they're fueled by this burning spite or anger. Happy people don't drive jays, unfortunately. So I was pissed off with the people who are not going to be able to do anything. With my mother-in-law and I wanted to prove it and you, a kid, you're not. For 12 years, I told my wife every single day, I'm going to retire 40. I'm going to retire at 40.
And I don't know how it would happen, but I'd say it. One failed, second failed, events company. I said, okay, we'll do a profitable venture, which is events not tech. It will make some money. It's a function of a guy runs away with money. And I kept telling her and probably she's hearing from her family that, like, this guy's loser, you're a doctor, you're making all this money. Whatever it is. Then the pandemic hit, started overworking myself.
And if you ask me in the summer of the pandemic, I'd still say, yeah, we're going to retire at 40. And my wife's like, how are you going to do this? I kid you not. There's something in this law of attraction. The week of my 40th birthday is when the wire hit my bank. The week of my 40th birthday. I had goosebumps. My wife was like, what just happened? Like, because my parents knew I'd say it all the time. So I had this spite, right? And then here was the key realization.
I had this spite, cashed out decently. Me and Alex still own almost 40% of post. So this is the thing. If you're a bootstrapped company, just if you have customers that are paying you and the customers are not leaving you and they're happy and you're growing, you don't have to grow 2X, 3X unicorn porn style. Even if you're growing 30, 40%, just stick with it. At 10 million or after, magic happens. You had mentioned the investment that the capital you took was private equity. Right.
It was growth equity, which is they like to say they're friendly like VC, but they're somewhere more in between along a P. I mean, can you explain the difference between, like just for listeners, what is the difference between VC and like a PE firm? Yeah. So a PE firm just mostly buys out your company and then rolls it into whatever thesis they have. They may own about your companies or own stakes in a bunch of companies, say they roll it in.
They lean it out and grow it efficiently so they can have a bigger multiple. A VC just invests in your company and doesn't want to run your company for you. They're like listen, we're leaving your vision and your passion and we're going to invest in, you know, maybe it will help you out, but like really we're going to invest at the earliest stages. A growth equity firm is somewhere in between. They're not as hands on as a PE, but they're also not as hands off as a VC.
They'll buy anywhere from like 20% to maybe majority in your company. They'll liquidate the founders. They'll still be involved. So it's like PE light in my view. PE usually are doing bigger deals. VC, a growth equity will do smaller deals and they're like PE light. So they're really a combo of that. And so what happened was we poured in all this energy during the pandemic. When events went offline, we took everything online, right?
We started doing two live webinars a week, two YouTube's a week, two podcasts a week. And we started growing, we started seeing leads coming through. And we hosted an event, get hosted an event in Toronto, attraction event. And one of the partners at the firm that we took money for them was a speaker. We had invited them as a speaker. They love the experience.
They're so much that she connected me with the founder of the firm and he reached out saying, Hey, would you be interested in joining our venture partner network? Venture partner is really not on payroll, but like it's a deal flow partner at VC firms. They list this right venture partner and they give you some upside in the deals you refer. So he asked me, is like, Hey man, see that you have a massive community. Would you be interested in joining our venture partner network?
And I'm like, listen, as it is, I'm slammed running this community on the side while actually running a main business. So it's going to be hard for me to dedicate any time to this. And he's like, Oh, what's your core business about? And I told him about both. And he was like, what? You sell $100 bills for $20 and you've automated the space. And he's like, let's talk. And we had a couple conversations and that was the summer of 2020.
And then strong due diligence followed after we turned our term sheet. And then the deal happened week of my 40th birthday. Alex was a big key in igniting that, Hey, this money of the table is the most important thing because I genuinely, I'm not wired to think about money first. I don't know it's upbringing or whatever. Like all my life, my grandparents included, they do just, my grandparents grew up in the slums of India. And like, it's always like gift first community.
And I'm not saying getting paid is not gift first, but it's just a wiring in your brain. If you have two paths, if it's like, Hey, you're going to get paid for the speaking gig, $3,000, $5,000, $10,000. And you got to go to Australia and the expenses paid. And it's going to be with this boring audience of consultants or whatever. Like, let's say coaches or real estate brokers, whatever. Like there's something that I don't resonate with.
Or Jason Lumpkins says, Hey man, come to Saster and you're on stage. I'll let you MC and it's a free gig. I likely will go to Saster because my tribe, that's how I think. Which is bad. That's why I need people like Alex, like my wife to. And a lot of entrepreneurs are like that. And also physicians, doctors by the way, they don't think about money first and that's why they end up being piss poor a bit. And they get lucky once. They make money, like especially entrepreneurs.
A lot of doctors, they spend everything they have. They don't think about money management or things like that. So anyway, so this story here was I was pushing out. I'm like, Oh, we got these guys interested. Why not talk to every other VC? And Alex is like, man, no other VC is going to let you take money off the table. Yeah. I mean, that's interesting because like that's the thing that founders don't know is that like they think, Oh, I took some VC money or I'm growing this thing.
It's either I run this as a ground or I sell it, but they don't think that there's a middle ground, which is either growth equity or private equity that which is structured differently. But you have to get to a certain cap or a certain ARR for that to be meaningful for these firms, right? Exactly. And then my wife comes to me and she's like, all your life you've worked for startups. You've never made any money, which just tells you that this 99% is so true, 99 or 10 startups fail.
But you are at a seven figure ARR. So you were not living well at the time? We weren't because the thing is we were investing everything back in the company. We were living okay. We had just started to live okay. And okay was a function of our wives being like a professional lawyer and doctor. Right. But Alex lives in Vancouver downtown. I live in San Francisco Bay area.
You need a family income of at least three to four hundred thousand dollars when you have a family, when you have kids, you have mortgage payment, you got schools, right? So it's not easy. And you got to count for the fact that California has a high state tax, plus federal tax, you have lost like 50%. Also, you're not accumulating like lump sums of money. Like you're making it, but you're not like you don't have millions in the bank. You don't have millions of back. So that's the thing, right?
So the money was okay, but as a function of previous lives, I've only worked for next to nothing at startups or founding teams or my own thing. And so Vivi tells me that if you go and take VC money and for some reason, you're on the other side of somebody's zero sum game, then I can't keep supporting the family like this. You're going to have to get a job at like Salesforce for Google or Oracle. Just find a stable job.
So you were looking or just talking to VCs at the same time just to see what else was out there. I was considering we hadn't even gone down that path. And then Alex stopped me and Vivi stopped me as well. And it's great. But as soon as we started having more deeper conversations with the growth equity guys, they're like, what would stop you from proceeding? And they immediately had presented this money off the table. We like to liquidate founders so they're motivated to play the long game.
And that money, Alex negotiated double of what they offered off the table. And that was life changing money for both of us. So that happened. And I was so busy during the due diligence and already during COVID, we're not spending any time with the family. And Vivi tells me it's like, at least put your phones down, at least have dinner with us, whatever, spend time. They'll always be so occupied. And I'm like listen, when this deal goes through, we'll take a look at it.
We'll take everyone to Borabora. And Vivi would say, nobody cares about your one, two week vacation once a year. Stop to smell the roses. Spend a little bit of time every day that compounds. The kids don't care about the two week vacation. Smart woman. I obviously didn't listen. And we kept pounding through this. Fortieth birthday, week, the deal happened, wired the bank. And then we were like, let's book everyone to Borabora. My parents, my sister, Borabora was my dream destination.
A few days before the Borabora trip, I got COVID and I was hospitalized. I got the gene pool lottery. And probably the toll of having a bad lifestyle led to a shitty immune system, dream, keeps smoking all the shit. I'm hospitalized. I'm on oxygen. And they wouldn't even let my wife be a physician at Stanford. They wouldn't let her in her own hospital to see her husband. I found them like setting up a 24 hour Zoom.
So any time the connection went off, the doctors would come make me up to see it's okay, that asked me things like, do you feel suicidal? It just f's with your brain right now. And I'm like, what the hell, you're in so much pain. I had bilateral COVID pneumonia. So I put my lungs were shot. And I sat one day in the hospital and nobody's talking to me. There's 24, 7 Zoom and I started crying. I'm like, dude, what have I done? Like, life changing money in the bank. But this can't save me.
And if I died today, my biggest regret it is didn't spend enough time in the last 10 years with my parents, with my sister, with my kids, with my wife. I'm like, what have I done? And what struck me was my wife. I saw her, like she was on Zoom and she called Alex and she started crying. And she's a strong woman. She's a physician, ER physician. And I've seen her cry maybe only two or three times in our life. Once when her dad had passed away, it shook me. It freaked me out.
Obviously, Alex also got freaked out with that incident. The investors got freaked out. I was a single point of failure, right? They had just like liquidated as significantly and bought majority stake. And here are one of the co-founders who runs product, runs marketing partnerships. The face of the company is like, it might tap out. There was a press interview as a function of this 100 million credit facility we did to lend companies money for R&D or R&D lending product.
As a part of that, the press is like, why are you coughing so much? And they did an interview on my COVID study, the story. And in that article, I said, hey, if I could change one thing, I'd go and spend more time with the kids. If I died, that would be my biggest regret. But then what happened was we had just come into this money and brought in new partners to the table. So we went on a hiring spree, right? Everything is like growing. Investing growth now. You figured out product market fit.
You've got 10 million. Let's scale this. Let's grow this. And as a function of that, we started hiring a lot of people. Maybe I think in like six to eight months, we must have hired at least 90 hundred people. We brought in execs from big companies. I think that's the style of a lot of growth. They like to bring bigger company execs typically. So CMO, CTO, CFO came on board. Summer rolls around. I clearly remember is August 21. My daughter was nine now. She was I think almost eight at the time.
And she says, Dad, everything you said in that press article is a lie. Like, what do you mean? She's like, you said you spend more time with us. That would be a biggest regret if you died. But you've gotten worse. And I said, listen, companies like hiring a hundred people in six months and dealing with all of this in motion is chaos. And we got to make sure things are in track. So people who put their faith in the company are not thrown into a world of chaos.
And she's like, why don't you go and work for a founder who thinks like that so I can have my dad back? Wow. Because I got mine. Then a couple weeks later, Vivi went into labor for a third kid, Zane. I was at an offsite with Alex in Austin. And my phone was down. Usually I keep my phone like inverted like this to be polite or phones down. And a few hours or many hours later I pick up the phone. I got like almost 20 mis calls from her best friend. She's like, kind of douchebag, are you?
Where are you kind of thing? Your wife's gone in labor. They're not here. And obviously now this is late at night. So I got to find the first light in the morning. They're barely made it to the birth of my third kid. And as a part of this, right, when you see, I think it's Oshah who said this, all of our worries in life are nothing but attachment. All of our troubles in life are nothing but attachment.
I was so attached to both that it was both first for me day in day out, creating that impact, helping entrepreneurs get money, giving them resources, connecting them content, connections, capital. Just that was my, in my head I had a family, but that was my tribe. And I would naturally gravitate. And you know, that's why I started this conversation by saying don't watch somebody's lips watch their hands.
Even though I'd say like family and be present, but on vacations automatically I'm picking up the phone. I'm automatically checking in on people. I'm automatically responding if anyone wants a connection. So my mind was gravitating there. And a few weeks when the firm came in, of course, they started recommending certain people that they believed would be great for the company, I wasn't loggerheads with those exact CTO, CFO, CMO. I just couldn't work with them. I couldn't work with them.
I'm a zero to one guy. I truly also believe that you can as a company have Swiss Army knives and doers for as long as you can, maybe 20 million or more because they help you grow faster. When you bring big company people, they automatically gravitate towards what they know best, which is more process, more people, more process.
But is that the purpose of these growth equity firms is to bring in new people and eventually like get new people to run the company instead of cultivating the original founders? Hey, I like to take a second here to talk about my own company, Ewebinar. And our mission to rescue people from what I call webinar hell to give them back their time and save them literally hundreds of hours every month through webinar automation.
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Why don't you give our product a try and see for yourself. Visit Ewebinar.com to join our own on-demand demo or to sign up for a free trial. All right, now that I've gotten that on my system, let's get back to the episode. I think the key is with Pee Growth Equity, there's a certain playbook. They've done this hundreds of times. They've invested in companies at stage. There's a certain playbook. So when they look at you and your business, they're like, hey, you have these obvious gaps.
We didn't have a CTO. We didn't have a VP of engineering and we got to 10 million. We didn't have a CMO. We didn't have a VP marketing. Marketing was a department of one. It was me running traction and leveraging contractors. We didn't have a CFO. We had an also, Alex was CFO for the longest time and playing that role. So both of us, like Alex was doing all the back and stuff. He was pseudo VP&G, pseudo CO, pseudo CFO. I was CMO partnerships. Like, you're basically an individual contributor.
So their goal is to plug the gaps that you have. And now, because they've seen a certain playbook play out, so their recommendation is usually leaning bigger company guys who've seen the journey. But my macro learning from all of this is you've got to hire people who are relevant for your stage. And usually at 10, 20, you can still have Swiss Army knives and doers. Because when you bring big company people, they've not seen in most cases or journey from 0 to 50 or 0 to 20.
They've probably seen the journey from 50 to 500 million. And the journey from 50 to 500 million is a lot of optimization. It's like, what are the processes, what are the teams, what are the scaling in-fri, it's all in-fri, processes and so on. But the journey from 0 to 20, 30 is some process. But like in the beginning, it's all, you're a pirate, right? You're sticking elbows and poking knives to get ahead, right? It's more sort of ruthless execution. It's more doing. It's more being a pirate.
And then over time, you start adding process, right? But it's not process heavy at all. So I think what happened was we went suddenly from bringing an execution mode, everyone is an individual contributor to having process. And then I think that it became imbalanced. Went from being execution to slight process to all process and less execution. So that started to frustrate me because I would spend all my time talking to customers doing in the weeds.
And I started feeling like disconnected more and more from the business. I'm like, not only I don't know what's going on, but I'm just seeing more and more power points and slight presentations. I want to see freaking demos and I want to see dashboards and metrics. Did you not think that was going to happen? Like you had no idea. No idea. No idea, it's only a work of startups. I didn't think it was wishful thinking. And generally, I'm a huge optimist.
I start everyone here and then you work, you wake down. I'm a huge optimist. So I didn't think that would happen. But like, two months in I knew. Like one month in I knew. You became a huge company overnight kind of thing. And then you had all these enterprise level problems. You can't go and argue with your mechanic because he's been in the nuts and bolts of your car.
Although people have titles like president, CEO, CMO, in a company that's gone from zero to 10 million, especially in a bootstrapped company, those titles are you know what? Really you are in a bootstrapped company for the longest time. You are an individual contributor. You may have the title president, my title is president, I like to see you.
But we're doing, if you are playing with the freaking Excel file or if you're sending email marketing to invite people to events, if you are updating the website, I don't care your title is president or CEO, you are an individual contributor. So what happens then is you hire a couple salespeople or you hire some people to take over the load. You still don't become a CEO or president. You become a manager because you're managing the people.
Now those people to manage those people, then you say, you know what? Now I've added so many people under me, like it's more than eight that I can manage all of them. So I'm going to bring a manager. So then you go to becoming a VP. At a VP level, you're still involved in tactics. You're managing managers who are managing ICs. Once you are at a stage where you are just knobs and dials, where your strategy more and not execution, then you graduate to being a C suite.
So these C suite titles and startups are like a misnomer and because if you have even the slightest ego, you feel like, oh, you know what? This is s**t I shouldn't be doing. Or you think you're a lot further ahead when in reality, you're not quite there. And so we went from being individual contributors, at least me, to all of a sudden being C suite overnight. But the actions of C suite weren't what I was used to because I'm like, where is the execution? This is process. This is process.
You need a certain process to go from 10 to 28 to 50. But then it, like I said, we went from this execution, this process to this process. And so I saw the execution speed slowing down. I mind you, we still grew really well. But I saw the execution speed and the IC founder in me just got impatient and I was at longer ahead with the C suite, with the new C suite. And then it became clear that it was time for me to step down. I just had a kid. I almost died of COVID, all this chaos.
And so look at the decision. We started this conversation with, is money important? Money is important only if you can buy freedom, freedom to do what you want, where you want, with whom you want, and when you want. On your time, on your dime, in your prime. And so we cast out, couldn't go on that borrub or a trip, almost died of COVID, got into this tail spin of like the company going from 30, 40-ish people to 130-ish people.
Over ahead with the C suite, so step down from the day-to-day of the company. And then got depressed, got overweight, I'll call it. And then the market fell, like all the money is in the bank with some investment banker. And the market, I saw you lose your liquidity. It happened to me as well. Yeah. So you lose your liquidity, right? So your paper rich, on paper, I own a big chunk of boasts, right? So this is a function if you bootstrap a company to 10 and you do a deal that way.
You can still send 50-55% and still own 40% of the company and participate in the upside, right? And that is a benefit of bootstrapping. If you're venture back, what venture back founder can say that after exiting or making decent money, they still own 20% of the company or after taking all this cash into the company, capital into the company, they still own 20%. And it's, it's, Alex owns almost 20%, I own almost 20%.
So but the reality of the situation is when the market, and then living comes to me, she's like, what are you moping, right? Just wake up and smell the coffee here, right? Just get a grip on yourself. If something happens to you, your family, your kids are going to cry. The community, you know, you've done all this community work, it's all going to be gone.
And so that afternoon I had lunch with Adelaceans president and she said, you know, take a year off, take time off to do nothing, disconnect completely. That's what I did. She came back to be the president. And I talked to the shrink and my good friend who was in a similar situation and I kid you not, the number of people who are especially in venture or raise money and go through the similar situation or founders.
And there's some stat out there, founders who exit their companies, go through depression. Like it's a thing. So I talked to shrink, came recommended by a couple of folks and I'm like, listen, I had this great spite to prove my mother and all wrong. And I hit that, made life changing, decent money. But then now it feels like I'm not good enough to run the company to a hundred million ARR or IP or whatever. So I'm going to prove these guys wrong.
I'm going to go on this journey and I'm going to go strap a company to Unicorn status and he's like, hold up. I understand the mother and law you got to deal with this woman. Yeah. I realize what is your relationship with your kids and like it's not existing. So you'll go on this journey and it's like, maybe you'll do better this time because you know, you came from failures before both. But regardless, it's a 10 year journey.
If you go on this 10 year journey and knowing you the extreme person that you are, what happens at the end of 10 years? I'm like, let's say I built this great company, bootstrapped, life changing money, even more life changing money. He's like, what did you do with the money? He asked me, right? I'm like, these things and he's like, how would you spend it differently if you had another X? And I'm like, I still do these things. I don't know. I wouldn't buy a boat.
My life is not about booze babes and blows. So I wouldn't do any of this. I'd still do this. And he asked me, what would your relationship be with your kids? I'm like, shit, my daughter will be 20. Shari doesn't know I exist. And I got two other kids who'll be in their teens. And he's like, I want you to think about that. What matters to you? And then I thought deeply, and I was overweight fat.
Like, I'll show this picture because I think it's an important one to show that depression has a face and what it looks like. But that's what I had turned into. Really fat, overweight, unhealthy lifestyle. And so I thought deeply, and I'm like, geez, this is right. Who am I trying to please you? Who am I trying to prove wrong? And then it sank, right? All my life, I'd say, success, looking for happiness. The money came. Where's my happiness? I'm miserable. I'm depressed.
My relationship with the kids got even worse and I just cocooned myself away, dealing with this. And I'm like, I have some f***ed up values that I need to question. Like I got to go back into my upbringing to question these f***ed up values. Or go back into why I have these values of all money defines everything. Money is a definition of success. Some values were good, like I care about community and people first. But the other was chasing money as a mode to success was bad.
I had this peloton bike in the room that I turned into clothing rack for two years. I dusted it off, hopped on the bike, and everyone sank self-care. And the instructor was coming off maternity leave and she goes, self-pity is toxic. One crank, one shift, one walker on the block. And the eye of the tiger was playing. And she jaz-me up. And she couldn't ride as fast. But over time that one ride turned into two, three. Now, eye of the tiger has become my morning ritual.
Wake up, thank something good that happened. Bang out 50 push-ups. And then I started realizing, what are the values I truly care about? And it became family fitness friendships. And so my conclusion to that whole exercise was, money is good so long as it's a mode to freedom. You got to ask yourself, what are your values? And this is where actually founding relationships, business relationships, love relationships fail because people don't ask what values are.
If you don't align on values going in, things will fall apart as you leave. So for example, say you're two founders. If one founder doesn't respect the other, thinks that person is a shitty engineer and the other person thinks sales is a nothing job, then you eventually going to fall out and hate each other. Or if one founder thinks like any means possible to get money, whereas the other founder thinks I just want to build the best product possible, then there's loggerheads.
And so I think one thing I've learned now, and it was a very awesome founder, Jafar, Owen Atty. And he's the founder of barley. But he had an exit before. I think that was also Growth Equity funded, Lupeo. And he told me this at a very critical time, that it's very important for founders to write down, what's your personal definition of success? How much money do you want to see in your bank account? How long do you want to run the company?
Is there a version of the company that you don't want to work for? The last one, is there any downsize to raising money right now or not? And that is very crucial because how many founders you know write that down when they go in? Have you written it down? I have those questions written down. But I haven't answered them. Yeah, what's your personal definition of success? How much money do you want in your bank account?
And for me, I had written a number, what house in my 20s when this whole thing happened with my wedding was called off two days before the wedding in India. So I wrote this number down. And I far exceeded that number, never changed. In a very long-winded way I answered this is I think most people, although they, especially venture back founders, although they don't, they say, oh, you know what, I create impact, I don't care about money. Everyone probably mentally has a number down.
And they probably surpass that number or they're hitting the lifestyle. Like basically if your lifestyle doesn't dramatically change and you're finding joy in the work you're doing, I'll keep pushing. The day I don't find joy in the work I'm doing, I'm going to piece out. Knowing what you know now with how, what happened with the company where you are today, like would you have done the same thing when you did it or would you have chosen a different path for the company?
You know, I would do the same thing over and over again, not change a thing. The only thing I would change is realize that all of our troubles are nothing but attachment. I would not be emotionally attached to the company and it's hard, hard to do. But if I knew then what I know today and this is where this attachment would lead me through depression and I'd just be this attached, I'd spend more time with the family, I would value other things, right?
And so now given family, fitness, friendships are my values, anything that takes me closer to that, I'm all in. If it takes me farther away from it, I'm not doing it. So you got to start writing down what brings you joy and what doesn't. So I'm a big proponent now. If I had to build another company again, would figure out the life you want to live, your values, write down your values and write down what your personal definition of success is. And the intersection of that do something, right?
Like your values are fitness, family, freedom, whatever it is and your personal definition of success, how much money you need in the banking account to make that happen. There's a Venn diagram there, do things there. Yeah, what advice would you give to founders who are going through the process you went through of looking for capital partners? Can you share a little bit more about like what terms I should look for for example or like how they evaluate good partners versus bad partners?
One thing is highly underrated and I don't think most people do. This is because the media has perpetuated this addiction to unicorn porn and VCs and taking money has been put on a pedestal for way too long. See, again, not everyone in the situation where they're fortunate where they have good revenue, they had good margins and they can command the VC or whatever, right? Sometimes you need the money and you need to pitch in any case, values alignment, right?
And how do you find out what VCs will align with your personal values? Talk to other founders, back channel it. See all their portfolio companies, hit up to a three portfolio company, see a network either. Yeah, it's like a job reference. Most people don't do that. Exactly. And don't ask people for references. I don't want to know your reference from you because you're going to give me the best reference. Look at all their portfolio companies. It's an easy hack, right?
You can go on a crunch base and see all their portfolio companies. And if a company is growing in the venture world, they'll have a most recent funding around within the last year or so. If they never raised in the last few years, hit up those founders because likely they are probably not doing as well if they've not recently raised because the venture game is raised another round, raised another round, raised another round.
Now ignore the current times, but it's usually like every two years your raise or not around every 24 months. So if they've not had like a fundraiser then in three years, that means either they're very profitable and doing extremely well or they're doing s**t. So contact those people and say, hey, what is the best board meeting you had? What is the worst board meeting you had? What is it like working everything off the record, right? Kind of thing.
So do that reference check firstly to make sure they're bullish about your space. They're like a romantic when they listen to your business. Their eyes open and they go out of their way to make connections. When we spoke to our firm, Chris, and there is the partner at Chris Livingston. Fantastic human. He just went out of his way to make all kinds of connections and do things. And they came to the meetings, understanding the business so well. It's like they were part of the business.
A lot of times you get shoved around to the analysts or associates. You get a token in somebody's due diligence, right? Your number X on somebody's due diligence pack and now you're getting canned answers. When the partner comes with a team and they're so well researched on your business and they're like, you know what? Have you thought about like expanding here or have you thought about adding this Ancillary product line or have you thought about this person and they engage in dialogues?
That's very interesting. If somebody comes and tells you, Hey, Melissa, I went through the webinar. I really love the product. By the way, have you thought of moving this? I was looking for this particular feature and it wasn't very apparent. Have you thought of moving it here? The two things that come to your mind is firstly, he would have had to go very deep in the product to even realize I have that feature.
And for that to do, he should be genuinely interested because this is not a feature that every casual user. One you've referenced back channel through the community, they're underperforming portfolio companies and what the interaction is like and some good ones, you know, how are they through the tough times and good times and two, are they romantic to your business? Like are they in love with your business? When you're in love with somebody, you're proactive about them, right?
Like if you're trying to date somebody or whatever it is, you find out stuff about them, you surprise them, you delight them. So what are they doing to delight you or two things? Because otherwise, 90% of investors, it's a commodity, it's capital. You know, I keep saying this over and over again. The media has perpetuated this addiction to unicorn form. In reality, the world is run by camels, horses, donkeys, cockroaches, right? That's the day-to-day business.
So then these guys go and raise money from wealthy institutions and wealthy individuals and they got to promise them a return. This is reality. To promise them a return, they got to invest in high-growth companies or highly profitable. Some thesis they have, but they need to deliver a return through their limited partners. So they don't do a portfolio construction where, okay, this company is going to, I've raised $100 million.
This company is going to return me $10 million and this will return me $40. And they don't do the math around 10 companies like that, right? They don't look at every company. It's going to be a billion dollar company. They want their fund to like 10X, 100X because they live their life on raising the next fund and the next one and the next one. Maybe the first fund is like a couple hundred or a couple tens, then it's like 400, then it's like 600.
They all have this career path and the career, you can't build a career path if you don't, in investing if you don't return money. A lot of the times though, just a natural game, it's natural instinct. VCs and founders just out of the gate most of the times are not aligned. Founders want to create impact and run the businesses where we started. Most people like, where did we start? Most people want to create impact.
If you, all of a sudden, came into a few million dollars and you didn't have to sell a webinar just asking you this, right? You sold half of the webinar, came into a few million dollars and you could live the life you wanted. You would probably say, hey, the webinar is going pretty well. I can still get a lot of money from the company. So why don't I just keep running it and run it from anywhere. Great lifestyle keeps my brain wired. This is how a lot of founders think.
Like this supports my lifestyle. I don't need like $50 million. I don't need like jet money kind of thing. You're thinking like, hey, this has a good lifestyle. I'll keep running this business and growing and see where it goes. It's magical when you get the 10 million because even if you grow 20, 30% year over year, which is considered slow growth in 10 years, you become 100 million or seven years, you become 100 million revenue. You look at UI path.
10 years, they were a million in revenue and then boom, exploded. So it's about playing the long game. So when you say that all those things, most founders are coming from a perspective of, I want to create an impact in the world. VCs are coming from a perspective of how do I return the most capital to my LPs? But is the growth equity path not possible for companies that have VCs invested? Like is this really only a bootstrap founders route that they can take?
In most cases, it's a bootstrap founder or a capital efficient founder because otherwise it's messy. They have to buy out the cap table. And also like a growth equity thesis is not unicorn porn. It's a sustainable growth and a decent exit. Growth equity usually looking to make five to six X their investment, five to seven X their investment in most cases. So if they invested, say, 30 million dollars, they want to make five to seven. But what's the end goal for them?
Are they going to take it public? Do they want to sell it to someone else? Because you guys still own like 40%. Almost four. Yeah, whatever path the natural course of the path is, they don't disrupt the founders too much. They're like, okay, let's see where your vision takes this. If it's IPO, it's a boom for them. If it's a billion dollar exit is also a boom for them, but it's a few hundred million dollars is still like seven X, right?
They won't cry if it's seven X. Most VCs, if they put in most venture traditional venture capitalists, if they put in 20, 30 million in a company, getting like 150 million exit doesn't make them look good when their compadres are getting like unicorn porn on their freaking playlist, right? So that is a thing you have to think about. Yeah. I want to be conscious of your time, but I do have one last question for you.
What are some final words of wisdom that you want to leave with our listeners today, who are bootstrap founders, focusing on driving growth and profitability? Do things you find joy in. And if you don't find joy in your company and it's at a certain size, reinvent your job in the job. What that means is founder and CEO are two loggerhead titles, right? Be a founder. Don't try to be a CEO.
Be a founder, meaning maybe take on a new market, maybe take on a new product line, maybe take on a new geography, maybe take on a new growth channel and deal with it, right? Sometimes you just get bored of doing the same thing. As a founder, it's your job to find joy in what you're doing, unless you completely hate it.
And a girl company, if you can't find joy in it, and if you don't find joy in it, outsource the sh** that you hate doing and even give away your roles to consistently reinvent your job in the job. And what might happen is you might take a new growth channel and that might explode and drive new growth from the business because it has your founder passion or you might take on a new market and it might explode because of your founder passion.
It's horrible to do things you hate and that are mundane that you don't find joy in versus doing the one thing you find joy in and you'll drive it further. That was my big realization. The second thing is money is a means to buy freedom. Just keep that in mind as you go along. It's not worth anything to anyone. If you have $50 million in your fifties and you're burnt out and can't get it up, can move, can't do anything. And then the third thing is self care is not selfish.
It's the only way you can create value in the world. Echoing Atlassian CEO, I knew, prioritized time for self care whether wake up and work out, exercise releases and dorsans in your veins that harms the feeling of stress. And so wake up, work out, spend time with people you love. Like do things that bring you joy. Now you may say coding every day, 24, 7 brings you joy. So be it. Then maybe code something else on the side, work on some hindsight.
Do things that bring you joy because what will happen eventually, maybe not your one, not your two, but you're going to have in this journey. Like I said, like look at it. Couple startups failed. Then once started doing okay, then I had one of my kids twins passed away. Then the exit came about. Then I almost died of COVID. Then found myself out of the company. Then God depressed. It's always this ups and downs. Money and fame and success and power. They're fleeting.
They're never going to bring you happiness. You've got to find joy in your life and do the things that bring you joy because what will happen is you'll have this roller coaster regardless of how successful or not your company is. Your personal life will continue to happen. And you'll face plan when that happens, like when things don't work out. And then you'll say like I only did the company. I only ever did everything in the interest of the company. I didn't do things that bring me joy.
So balance out, like make sure you're doing something that brings you joy every single day of the week because of compound interest on that is enormous. And that's what I experienced. And the last thing is environment. I mean, I know a lot of people are talking about, oh, you only got to be in the office in person. I don't believe in that. We built a very successful remote first company. And there's other ways to congregate people rather than having a water cooler conversation every day.
You can do events and meetups and fly people to different places once in a while. You can do a number of things. But the reality is your environment is probably the number one impactor of your mental health. So if some place is dragging you down or the people or whatever it is, switch it up, change the environment. I move to Dubai, change my life. My quality of life changed 10X from after 25 years of being in the West, 12 years in Silicon Valley. So those are four pieces, I would say.
Well, thanks so much for being here to share your experience and your perspective. I always learned something talking to you. And I also forget how much you've done in such an experience as such a short time. How can people connect with you? On LinkedIn, Lloyd, double L, O, Y, E, D, Lobo, I have a book coming out, by the way. So as a function of leaving the company rather than sitting on our idol and focusing on my health, I thought to myself, what is the most impactful thing all my life?
And I was a refugee of the Gulf War where the community came together to rescue the country, took us to freedom. I realized that day we weren't sure if we were going to live or die, we were on this bus going on the high be of death. But everyone on the bus was singing and laughing along the way.
And I realized it's neither the destination nor the journey, but the companions that matter the most, who you're with can put you in the best frame of mind and turn you into a king or who you're with can screw your brains, drag your energy down and turn you into a peasant. The second time community helped me was when we were building traction as a side hustle and traction helped bootstrap both to it figures ARR.
And the third time community helped me in a very massive way when I was depressed and I picked up that peloton and was like the instructor and the community of people high-fiving me and it really helped improve my mental health. So I decided to write a book on community-led growth interviewing hundreds of community leaders from Harley Davidson to HubSpot, Saster, Jason Lemkin at Saster did the foreword on it.
And so we'll be on community-ledgrowth.io, community-led growth.io or loy-loy.com in a few weeks will launch it. But that gives you 12 rules to build iconic brands with raving fans. Awesome. Well, we'll include that in the show notes for sure and share that with our community. If you enjoyed this episode, don't forget to subscribe to ProfitLED and be notified of new episodes head over to our website profitled.fm to see the show notes of this episode as well. Well, Lloyd, thanks for your time.
Awesome. Love and Peace. Thanks for listening to ProfitLED. If you enjoyed this episode, we hope you will subscribe to the ProfitLED podcast and head over to our website profitled.fm to see the show notes of every episode. You can also join our mailing list to be notified of new episodes or when we have interesting products and resources to share. We promise to only share things you'll actually care about. Thanks again for listening. Bye now.