Raising $100 Million while beating COVID-19 - the story of Lloyed Lobo of Boast.ai

Lloyd Lobo Co, founder and president at both that just closed their funding round of 100M dollars and Intel erased 123M dollars up to date.

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And they will talk about how they got to this point how they manage to bootstrap it for a very, very long time before raising money and why Lloyd decided to bootstrap versus raising money. Right away.

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We'll also touch onto cobit because Lloyd got cobit straight after closing the rounds. And today we'll talk about that as well. So let's kick it off by giving us some background on yourself and on both.

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Definitely, thanks for having me here and, uh, it's been a great pleasure and the experience even before when we were prepping is great. Um.

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So quick background on myself, I'm an engineer turn sales and marketing, turn product or other. Sorry let's cut this out but, like, a quick background is, I'm an engineer turn product person, turn sales and marketer, turn founder.

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So, I have a variety of different backgrounds as it ties to product and go to market functions how I got started. I mean, I'm a refugee of the Gulf for literally immigrant.

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I my parents, I was born in Kuwait in the Middle East, and after a, when I was in 10 or so, Cal, forehead, we escaped out on their long story short, moved all over and made our way to Canada, studying engineering and Canada.

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That's where I met. My best friend, my Co founder.

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And and went to computer engineering there.

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After engineering, I moved to the US and worked in product and marketing growth at a number of startups after engineering. My Co founder got into Johnson and Johnson engineering leadership program built software.

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Then did a startup that startup failed felt he needed to study accounting, studied accounting, long story short. He ended up at.

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A big 4 accounting firm running their research and development tax practice. Now, if you're unfamiliar globally, hundreds of billions of dollars are given in research and development tax incentives by the government.

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Uh, to fund businesses, but the application process is manual it's cumbersome and it takes a long time to get the money. So, around the after him doing this for a few years, he called me and said, hey, man, this process is broken. It's manual.

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Let's work on a product that streamlines and automates it and here's my best friend and I was looking to work on something. That's interesting. And because he asked me, I'm like, I jumped right into it and there's another angle there. I was miserable in the previous startup.

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I was working at because, because the CEO there, so everyone like lemons, he would make comments. Like I see everyone is 11. I want to squeeze as much as possible, but 1 thing was really super interesting because I spent my family's in Toronto.

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I was I was I was in the US at the time.

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And I was working late hours, you know, it's a startup you're working late 8 910 sometimes. And the thing was, my wife was in residency at a time. She's a doctor, she was just after residency.

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I mean, just after med school, she got a residency and she was working crazy hours residence, worth 100 hours a week. So, I used to be in the office too late work on on projects and whatnot.

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Why don't we get started going home early like, around 6 and I get an email after a few days are going home at 6 and 6 is not only, by the way and I get an email saying, hey, I used to like it when you're in the office till 8, 9 o'clock what's making? It will go early.

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Your wife is a resident, your wife is a red is resident working hundreds of hours.

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What do you need to go home for? And I just responded with my parents are in town, right? My parents were in town and that day is, coincidentally, is when Alex called me with the idea of, like, he was saying, let's do this. Let's do this and I called him and I cried on the phone.

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I'm like, man, if we can build a, if I can help build a company that I want to work for.

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I'm in I'm not into this, like, hustle, 24, 7. let's build a company where people aren't happy.

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And and they can have a balanced life and still girl.

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And, you know what, I've been a part of for 3 or 4 venture backed companies, and it's always been that hustled horn work, 24, 7 and here, we've grown the other way. And so, you know what, I think mental health.

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Is is key, I think work life balance is key, right? At the end of the day.

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It doesn't matter where you're going, or how you're getting there. It's not the journey. It's not the destination. It's the companions that matter. And if you, you might be on the shittiest journey and you may have the crappiest destination.

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But if you have great companions, you're singing along the way, and you're looking out for each other. So that is what's really, really important. And that's how you can build a long lasting, endearing company.

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And that is the quick, not quick, but sort of backstory here on me.

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This is awesome having a, she has journey and she is destination, but nice convenience that says just perfect. That's literally the description of this star world. Absolutely. Love that. So eventually is doing great.

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You most crafted for quite some time we're going to talk about it and just a 2nd, but 1st.

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Congress on closing a 100M dollar round. This is huge. Can you tell us a little more about that round? What was it about?

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Yeah, definitely I'll tell you, they happened in succession they were happening in parallel. So the 3002000 Series A, we raised was to fund operations and scale the company we got to over 8 figures in revenue with 4 salespeople. No marketing team.

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And, uh, a small less than 5 person, engineering team and customer success. Right? And so we got, we weren't raising money at all. It was during the pandemic and.

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We're bootstrapped founders, like, why would we want to raise money? What's incident is like, our mission at most is to help innovative companies become successful. Now most people say I, everyone says that that's that's a lot of crap right? But if you really want to see.

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If people are true to their mission, you don't read their mission statement, you watch their actions, and we started this nonprofit community.

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Called traction and today it's got 95000 subscribers. We do 2 webinars a week. We do monthly dinners in different cities.

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We do quarterly founder, funder, matchmaking events, and we do an annual big, big conference, and everyone from the CEO of Twilio has been to our conference to heads of growth at LinkedIn.

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And a lot of like, exit senior entrepreneurs, like, from Atlassian Zoho and so on, and they come to our events to share advice.

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To help companies scale and grow their businesses and it's a non profit community. All money goes in back into the community.

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So, we started started that community and it's grown significantly the last few years and we're doing a quarterly founder founder, matchmaking event. That's how we met met the radiant capital guys.

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And, like I said, for me, relationship is more important than the transaction. And so we met the radiant capital folks.

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And really, really liked liked how they thought about things and business and we weren't tracing by the way they were asking us to join their venture partner network.

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And we're like, I don't know, like, you know, business is busy and it's a, you know, it's hard enough, running a business than to be a venture partner fund kind of thing. And so, as we were talking through it, they got to learn our business.

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And they're like, you have a massive business, like, you know, every company is innovating and you can get them money in a streamline automated way. So they don't have the headache.

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It's brilliant, right and so we started talking and having these conversations with the regional capital folks who were doing our, a, and as we talk to other founders, they invested in 1 advice I saw that was consistent.

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Those 1 founder, his name is Martin. Who is the CEO of apply board? It's worth 1 and a half 1B. He said during the pandemic, they closed a series. C. I think.

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And their round wasn't coming together, and 1 of the partners at radiant Capitol previously had, was with another fund that invested in them. But he also, I think angel invested in them. And Martin asked him like, hey, I'm stuck.

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Can you send some money kind of thing and and he.

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Talked to him on a Saturday and on Monday he wired the money. So he's like, if these are the kind of people that surround you, who cares about anything else, like, optimize for the partner optimized for the people.

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And then I talked to like, some of the other companies that radiant capital had invested in, and the feedback was just great just 1 direct intros and and back channel. So, we felt like a good relationship.

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You know, that whole thing I shared about, it's about the companion that matters, and they've been great helping us through like, you know, challenges like, we're been a bootstrap company, find a C. T. O find Mark heads of marketing that kind of thing. Right like, help there.

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And not help is not just help, find somebody, but actually help assess if that person is good. Right? What is the hiring scoring rubric? So, that relationship, as we start developing, we thought it made sense in parallel.

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We were also talking to the a capital folks, and that was for a 100M credit facility.

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And that is interesting because if you do a year of R. D but that money is locked up, right? You can't get that money until you filed it for taxes with the government and the government processes it. So, for every dollar, your current R. D.

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It's locked up for almost a year. So what what the capital guy says is why don't you guys do a fund.

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Where rather than companies waiting, you're already automating already tax credits, but you still have to wait for tax season government deadlines, but you're doing it in a sort of real time, proactive fashion. Why don't you front load the cash like a debt fund?

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So, for every every month or quarter, they incur in expenses, you give them the money now and, you know, we're like, great. So it worked out in succession. We did this 23M dollar Series A, to scale our operations where beef up.

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Sales marketing, technology, customer success and take it from, like, 10 to 100. then we raise the 100.

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A 1M dollar credit facility to front load cache against already, like, similar to our financing, which you may have heard of.

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Nice this is insanely great and by the way Emma are financing, it's a beast. Absolutely love it. Absolutely. Love for this industry going in general corrate work.

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Honestly, just to this moment, I did not quite understand what exactly both the I was doing. Now the in your sentence, I'm super pumped to keep talking about. Well, let's focus. 1st about.

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Let's talk just a little bit more about bootstrapping and how you managed to get to this point while being completely bootstrapped. So why did you decide to bootstrap initially? Instead of raising money? Yeah.

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So the bootstrap model was having been a part of.

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Seeing the venture journey we knew that.

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You know, it's not for everybody, right? And also.

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I think the fundamental belief here is if you can turn 1 dollar into 3 or 4, then raise money and a.

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We didn't when we started, we didn't think this was a boot. This was a venture bankable venture rather because we're like, you know, it's an industry that's traditionally services. People are not going to understand it.

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And then we, we are working on other companies before. So, like, the best way to do it is get customers. Like, I, I always say this ignore the hype cycle.

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Focus on customers have conviction about the customer fall in love with the problem you're solving for them. Make them become successful.

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If your customers will pay you and keep using you and keep referring you to others, the money will follow and it's been the best journey. I think we stretch the bootstrapping a little too far. A little too hard looking back.

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I think if I could change would make some few more key hires.

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We would have maybe taken money before, but hindsight is always 2020, which gives you 1 great thing. It gives you discipline.

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And if you look at companies like Twilio effectively, you know, they didn't have, I think, I think they ran very lean in the 1st year or so, until they raise money today, it's worth 70B. I mean, with shopping gives you discipline. I think I wouldn't go back on any of those hardships.

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So it's like.

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How to sell?

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And nobody knows you, how do you, how do you like, I've learned everything from sales to, to doing se out running ads to building community and what not right I mean, like, when you're starting out, the key to bootstrapping is.

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And the key to building any business, I think to at least 10M is this.

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Fall in love with 1, kind of customer deliver 1 kind of value where your product or service, and get them through 1 kind of channel.

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And if you do that consistently, you can build a big business.

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But if you focus on 5, 6, 7, 8, kind of customers, and trying to deliver, like, 7 different things for them, and you try to invest everywhere else, that lack of focus is going to destroy you as a company and company I was working at previously.

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We ran I ran product and growth there and speakeasy.

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We had just way too much going on. Right? We were we were building a plot product for salespeople.

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It was like, in a way, I for sales, right? A connect to your connect to your app.

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And you to connect to your call and tell you how to prepare for the call.

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I tell you what to say during the call automatically and generate a next set of action items, but when that company launched, we were running ads, lots of ads to do mobile app downloads. The problem is.

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Because it came with free calling everyone that signed up, signed up for free calling. So, there was no 1 customer profile butchers, bakers, Candlestick makers. Everyone like Bernie Sanders group were using it for election.

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Pastors were using it for preaching taxi, taxi cab drivers are using it for dispatch and it was blowing up the money because it costs money on these calls and who doesn't want a free international calling up.

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And then I still, I still remember they were like, over 1015000 people using it. I said we need to shut down free and make it pay.

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And the general consensus was, if we do that we're gonna lose everyone, and That'll show that, you know, our growth shrunk, we won't be able to raise the next round of funding. But I'm like, I can't do an ideal customer profile based on this audience is all kinds of people using it. Right?

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So we shut down free when to paid. Right? And, and when we went to pay the only people that stuck around were salespeople, they loved us.

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We built a lot of product for them, but then what happened, we ran out of money because you didn't focus on 1 kind of customer and when when you did focused on 1 customer, and they loved you, you didn't have enough traction to raise the next round of funding, and that is the key thing.

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The key thing to bootstrapping is focus relentless focus 1 kind of customer.

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Figure out 1 channel offer 1 service to do that over over and over again, then you can scale it.

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Absolutely love you're dropping so many quotes. They are going to show up on my Twitter for sure that I absolutely love it. Thank you so much for generating content for my Twitter. So let's talk just a little more.

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Few more questions about bootstrapping. So you're working on helping startups and other companies to receive those incentives that the government provides for the research. Right. Do you use any of the grants? Yourself? While you were building?

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And but mostly yeah, definitely. So, we got a huge grant, and it helped us build our dev team, I think, in 2019 and the grant was like, man, it's really interesting. What you're doing.

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You're collecting the data stitching the technical and financial to apply for this. And this could streamline.

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Processes for a lot of grants, so we got a grant for that and that, uh, that grand effectively help us get like some developers and, you know, get off the ledge there. So it was good.

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For sure, and we, we will continue to leverage.

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Nice and yet, for those people who are not quite familiar with grants 1st of all go to fundraising radio Dotcom and just search grants 1 on 1, just like some basic stuff on grants and also for those who are slightly familiar.

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And when I check out, if they're actually a fit for some grants, I interviewed founder of a company called.

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Grand start, so check it out and see if maybe you're good fit for some kind of grant that might push your company a little bit forward.

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So, now, let's talk about the most recent events, which is being I can hear your kids on the background, which means everyone is at home and you got it. Right? After you close around. Can you tell us a little bit more about that? How did it happen?

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How what kind of effect you have on your fundraising process?

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Yeah, so like, luckily, we close around and, you know, here's a big lesson for all founders that I'll say is very, very key. We fall in love with our customer. We have to fall in love. We fall in love with our customer and our business.

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We have to make sure that we have the same passion for the family and I feel like every couple of years I get slapped with this realization, right? Something bad happens to me to say it's like.

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The heavens above are slaying slow down, slow down and focus on what's important. And so what happened is my, my wife's and physician.

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And so she's been dealing with a lot of covert patients and, uh, I think around December, 23rd.

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We all tested positive for cobit and what had happened was we announced our fundraising, I think, like December 10th or 12 within 10 days of that time and I was saying, let's celebrate, let's celebrate it for the last 6 months. I've been saying we'll celebrate we'll have good fun.

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We'll close this round and it's going to be awesome. And so my parents spend 6 months of the year with us when it's summer in Toronto.

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And it was it was amazing and.

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I waited for so long to celebrate and this round closed and as were, like, got really busy after the round closed. I said, okay is the holidays to celebrate. We all got covered. We couldn't celebrate Jan. 2nd, unlike hospitalized unable to breathe.

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They put me on oxygen. They put me an IV medication.

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Honestly, I cried every single day and said 1 thing, if I can go back, I'll make it. Right.

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It's important to wake up and smell the roses every day and not wait for the big moments because, you know what? I'm.

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It's about doing things a little better every day, rather than going for the home run at the end, right? Mm. Hmm. Because if you're swing for the fences at the end, you you may go boom or bust. Right?

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Like, me, luckily, I survived to be able to tell the story and realize, but it's very important to appreciate the people around you and and understand that every day. And as founders.

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We tend to miss that. We take things for granted because.

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It's not the money in your bank account. It's the people around the tombstone that matter the most. And when you go, that's the thing. And I saw this realization, I think about it.

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I'm in the hospital for cobit. My wife's a doctor. She's not allowed to see me despite being a doctor in that hospital. So I'm sitting in this bed. I'm feeling like, I can't breathe. Basically I can't sleep. I'm on oxygen.

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I'm, I'm on IV. I'm I'm losing my mind.

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And nobody's allowed to visit me and they have a 24 7 zoom on and I'm like.

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Jeez, if I'm going to go today, is it going to be like this with people watching me on soon and, uh, it's it's a really, really crazy crazy experience. Right?

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So, it's like, and then, after that happened, I got better and then we announced the 100M facility, but it's, it's a good realization. You need difficulty in life.

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To appreciate what's good if you're always on a growth trajectory, you'll never appreciate it. Right?

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100%, luckily, in the startup world, there is plenty of bad stuff happening. So, yeah, I hope daughter's can actually appreciate as well and I absolutely love this story.

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I mean, the good side of the story, of course, I'm glad that you've made it to fundraising redo love the story ends.

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On speaking about communities, speaking about people around here, let's talk about the community built with both. Right communities called traction. Can you tell us a little more about it?

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Yeah, so our mission at traction is to help founders build and scale companies and help them grow. And, like I said, we do webinars a week. We do monthly dinners, which has stopped now because of cobit. We do an annual conference.

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We do quarterly founder, thunder, matchmaking events.

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Add in a nutshell, both mission is to help innovative companies become successful by democratizing access to billions in R. D credits innovation in incentives and non diluted capital.

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So companies can feel their growth while preserving equity and avoiding red tape.

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But to further our mission, we Co, founded and built this non profit community with our friends at launch academy to over 90000 entrepreneurs. We provide free access to all these resources and advice on building and scaling companies.

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Because, honestly, if you help your customers grow.

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They will help business grow if you help the community grow, they will help your business grow. If you help your team members grow, they will help you grow.

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It's not about asking for stuff and taking from people, but if you help enough other people get they want.

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You will get everything you want. Yep. And that's the rule. That pretty much. Every single salesman salesman. Anyone I think should follow. And most of people are doing this right now. And this is great.

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And this isn't exactly yet. Another reason. Why you should love star world, because people here just helping each other for no reason is ridiculous. And on this optimistic note, let's move on to even more optimistic stuff.

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So, can you tell us a little more? You've done? I assume plenty of fundraising in the past. And doing, in terms of both dot a, I can tell us some crazy stories there.

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Have you had any beach events or have you done any demonstrations that have gone wrong or something?

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Cool happened there. Yes I'll tell you. Probably not a boast, but a previous company had speakeasy and this is the funniest thing I heard there were there were we were pitching on the phone right?

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Like, conference, Web conference and just pitching pitching, pitching the CEO of the company and we were all on the call pitching and going added and going at it going at it.

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And I noticed that there's no feedback coming from the other side, and we're 20 minutes and then I pick up my phone and I have like, 3 dozen text messages. I pick up the phone and call and they're like, hey, man, we got cut off 5 minutes into the call we're trying to get in.

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We can, and that's why we've been trying to call you. Nobody was answering. I tell the city of the company is very important to keep dialogue in our active. Right? And during that, that was a funny thing.

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I think also speakeasy there was 1 partner meeting where we got to.

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And they asked for our gross margins, and they asked for the costs and we had no answer for that. So, that was that was very, very interesting. I think these 2 incidents are funny. Uh, there's a great incident attraction.

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So, this is the life of bootstrapping.

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With bootstrap when he did the 1st conference, my Co founder Alex and Ray from launch Academy. They're like, hey, there's not much budget. Let's do a conference.

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But and I was very passionate about doing the conference, because we had built, we were building a following so I called email all the speakers like Marketo hoot suite Postmates Twilio.

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And 1, or 2 people express interest, and then I reached out to others saying these guys are interested in a bunch of them confirmed, we put together, but because it came together so tightly, we couldn't find a venue. Right?

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We were like, we basically bootstrap it. So, we did a giant ATM on in a nightclub and a, and it was interesting on its own. It can only fit to 50 people seated, but we like created capacity for 500 people.

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And, like, you know, the lounges and everything and there was a stripper pole in the corner that we had.

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And all that stuff real funny thing was we confirming way too many speakers reconfirm something like 25 or 30 speakers for 1 day conference and so all the sessions or 15 minutes,

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15 minutes,

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15 minutes back to back to back.

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And so how do we keep this on time? Because the timer alone won't work.

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So we went and got a smoke machine and we put it backstage. And so every time somebody hit 15 minutes.

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And there are 1 or 2 seconds will hit the smoke machine when the smoke goes up.

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People see the smoke and they start clapping right? Like, started. So that worked really well now we get to 6 in the night. Imagine imagine drinking for a fire or you're doing, like a session at 609.

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And then the founder of was very popular. Chad was like.

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Clubhouse is popular today, so he flew in, he came and he was sitting with Frederick from tech crunch to do the session they went on stage, and as they were starting the session, the smokes slightly started to go out within 30 seconds. Why is Lloyd releasing the smoke?

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We just went on as we looked back. Actually, the smoke machine ran out of water and the drapes. We're catching fire ad to run and throw water on there. It was ridiculous. Hilarious.

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Right? It was it was it was unbelievable. We almost burden of the speakers, so that's the kind of thing when you bootstrap a company, you have these kinds of ridiculous experiences, man, you are definitely following your own advice.

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No matter what's the journey if you're having fun on its way as great as a great journey. Us I love those stories. Your background is perfectly perfectly great. Ryan.

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Of course here was very, very optimistic. No, let's move on to the last question of today's episode, which is what's your advice to be?

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Entrepreneurs, listening to this right now, my advice is this if you are getting into starting a company, and you have no idea about how go and join a hackathon or a startup weekend startup weekends are amazing.

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I got to know more about the startup world, going into startup weekends, because it teaches you how to build things under pressure. Right? You got 3 days to come up with an idea validated and pitch it to market market investors kind of thing.

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Like, do a few of those are really get your feet wet.

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And and the most important thing is don't do anything for the money. It's not the transaction. If you chase the valuation and go how higher higher higher, what happens the 1st time there's a problem either your investors are out or you're out as a founder.

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If you optimize for the relationship, they'll work along with you, because, you know, they feel personally personally responsible to that to the mission. Right? And so the most important thing is optimized for the relationship.

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Make sure you have passion and conviction for your customer because if you don't have passion and conviction for your customer.

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And you treat everything, you don't optimize for the relationship, it's a transaction. And what happens when you are in a transactional relationship.

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The 1st time things are shaky, or, like, uh, the 2nd time things are shaky or 1 for his out the door, the 3rd time, something is shaky, you're completely out right?

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So, making sure you have passion and conviction for the problem and you treat everything like a relationship is most important thing. And then, and then stemming from there is focused on 1, kind of customer deliver 1 value.

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And get them through 1 channel.

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Hello, I think I last year was no, I was facing that quote, because I wanted to finish it before and I forgot and now I've finished it. All right that was great advice.

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Honestly hackathons are absolutely great. That's exactly. Literally I got into the.

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Venture world through Hackathon that's how I got there and yes hackathons are ridiculously good. They are super helpful and you really get the sense of how the world works. So great advice on this brief note, we're going to wrap it up.

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My call to action is going to be go to the scripture says episodes are going to be a bunch of stuff. There there's going to be grants dot. There's going to be bootstrapped dot a.

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I am sorry, I keep calling also leave a link to LinkedIn and maybe a link to something else.

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I'll have to follow up with Lloyd to see if there's anything else that she wants to include in the description this episode but in any case, go there check out the links. There. There were hiring. We're hiring. We're hiring. We're hiring 50. we're hiring 50 positions in the next.

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Like, literally we're hiring 50 positions yesterday post for slash careers.

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We're hiring, come join us. Awesome company. We do an annual offsite summer exotic. Last day we went to cobble with the whole company before that. We went to Costa Rica before then we in Hawaii, and then we all get together during our big traction costs.

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And, uh, and really remote 1st, environment people over profits.

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Passion for the customer. Thanks. So much constancy. I love this. Just jumping in screaming. We're hiring. I'll make sure it's a labeling to both in the description.

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So people, if you are interested in working in, a really good, collective, definitely check out description check out. What kind of careers are open at both and as usually have a good date.