Omer (00:09.280)
Welcome to another episode of the SaaS Podcast.
I'm your host Omer Khan and this is the show where I interview proven founders and industry experts who share their stories, strategies and insights to help you build, launch and grow your SaaS business.
In this episode, I talk to Tony Somerville, the founder and CEO of Fleetio, a SaaS product that helps businesses automate fleet operation tasks and keep their vehicles and equipment running smoothly.
In 2011, Tony was working as a product manager.
He tried several times to start a business in his spare time, but just wasn't getting any traction.
Eventually he came to the realization that if he was going to have a serious shot at building a business, he had to quit his job and go all in.
He and his wife agreed that he'd give it a try for one year and if things didn't work out, he'd go back to a full time job.
After seeing how his father's business was struggling to manage its fleet of vehicles, Tony set out to build a modern fleet management software for small and medium businesses.
He launched his minimum viable product in about seven months and a few months later had his first 10 customers, thanks to all the time and effort he'd put in doing customer development interviews.
But he was only charging about $50 a month for his product and so there was still a lot of work to do.
Today, he's grown his company into an eight figure SaaS business, built a team of nearly 200 people, and has raised $25 million in VC funding.
In this interview we talk about how Tony validated his idea, built his mvp, tested pricing, built a content marketing engine and bootstrapped his business for the first four years and a lot more.
So I hope you enjoy it.
Tony, welcome to the show.
Tony Summerville (01:59.830)
Thanks for having me.
Omer (02:01.110)
Do you have a favorite quote, something that inspires or motivates you that you can share with us?
Tony Summerville (02:05.830)
Yeah, I thought about this and had a couple.
One of the ones that I've always liked is actually from Tom Coughlin who was a renowned NFL coach and his quote was humble enough to prepare, confident enough to perform.
So just a good reminder that have to prepare and be humble, but also confident in what we bring to the table every day.
Omer (02:24.880)
So tell us about Fleetio.
What does the product do?
Who's it for?
What's the main problem you're helping to solve?
Tony Summerville (02:31.280)
So our customers are businesses and other types of organizations all around the globe that have a fleet of vehicles and or heavy equipment.
So we have lots of different types of customers from trucking companies and transportation businesses to lots of construction companies and services businesses like H Vac Repair, Electricians, those types of companies.
And then we've been fortunate enough to be in an industry that's changing dramatically over the last decade or so.
So we have a lot of the self driving car companies using Fleetio.
We have a lot of micro mobility companies like scooters and Bikes, E Bikes, those types of companies using Fleetio too.
So ultimately they're using the platform to manage these different moving assets every day from an operational and logistics standpoint.
So think about maintenance management, understanding which vehicle is assigned to which understanding from an inspection standpoint, which vehicles might need repairs that are broken out in the field, having preventative maintenance schedules set up, and really just drives a lot of the day to day these assets.
So you can really extend the life of each one and understand the total cost of ownership and know when to replace an asset or a vehicle at the right time.
Omer (03:34.770)
Can you give us a sense of the size of the business?
Where are you in terms of revenue, the size of team customers?
Tony Summerville (03:39.810)
Well into the eight figures as far as ARR and we're about 175, approaching 200 folks today spread out all across the U.S. we're based in Birmingham, Alabama.
We've long been a remote first company and even have folks in Canada and Mexico now too.
Omer (03:53.330)
Awesome.
And what about customers?
Tony Summerville (03:55.970)
We have about 4,000 customers that use Fleetio and manage about half a million vehicles in the platform today.
Omer (04:01.970)
Are they mostly us or have you got a global customer base?
Tony Summerville (04:05.010)
Yeah, we're in about 75 countries with paying customers.
The majority of our revenue still comes from the US but we have a lot of customers in Australia, the UK and then a number of sort of countries with a handful of customers.
So that was one of the really exciting things about fleet management is tactically, a lot of the things that you need to do to manage a fleet effectively are pretty similar no matter where you are in the world.
And the things that are different are just kind of hours versus liters versus gallons and the different sort of ways of measurement.
Omer (04:31.710)
Okay.
And then in terms of funding, you raised, I think just over $25 million to date.
You founded the business in 2012 and I think it was for the first four years you bootstrapped the business.
Tony Summerville (04:43.810)
Yeah, so I'm a solo founder, started it in my house and bootstrapped for, yeah, about four years.
We did a couple of rounds of angel investment after starting in 2016.
One was 750k, the other one was about two and a half million.
And then we Raised our first institutional capital round in, in 2020 and that was a $21 million round.
Omer (05:04.240)
Okay, so how did you come up with the idea for this business and what were you doing at the time?
Tony Summerville (05:09.840)
Yeah, so before starting Fleedia, I was a software engineer.
Worked for a few years out of college at a bank.
Decided I didn't really love the large corporate world and the banking world, so joined a relatively early stage, fast growing SaaS company in like 2005, 2006.
Worked there for about six or so years in software engineering roles.
And then that company raised some capital and had the opportunity to do some business development.
We acquired another business and then I was a product manager for the last few years.
But I come from a long a family full of entrepreneurs.
Both of my granddads and my dad are all business founders or entrepreneurs themselves.
And so I always had it, my DNA I guess.
And the last couple years I was at my previous company, I was just really thinking a lot about ideas through the lens of my dad's business, which is a big electrical supply, electrical distribution company.
And I had grown up working in that company.
That was my summer job every summer.
And you know, I was very familiar with kind of a little bit more of that sort of blue collar industry.
And I would always think about like, what are the types of things that business like my dad's kind of struggles with from an operational standpoint that software, particularly software as a service, as everything was moving to the cloud and we had clearly mobile was going to be a huge part of the future of how people sort of worked.
And it sort of occurred to me that they had this fleet of vehicles and it wasn't necessarily a core competency of theirs to operate them every day, but it's very important for their business.
And just saw like that as a seed of the idea, I guess you could say.
And then, you know, really spent a lot of time in the early days just talking to lots of different types of organizations and really trying to pinpoint if there was truly an opportunity there to really build a modern fleet management system.
Omer (06:47.190)
So what came first, the desire to start your business or the idea that led to starting a business?
Tony Summerville (06:51.990)
I think I always knew I was going to be an entrepreneur even from being a kid.
So I probably always had that desire.
I think it was just a matter of in my own, just sort of personal journey, I wanted to get a lot of experience and be able to.
I really enjoyed the aspect of building software and building those skills allowed me to actually build Fleedio without, without any outside Capital, but then also spending time as a product manager too, kind of helped me understand, like, how do you validate ideas?
How do you really understand pain points that potential customers would have and so on and so forth.
So, you know, I always knew I wanted to start a company, but could built some skills in my professional career prior to starting Fleetia.
That helped me kind of hone in on the idea and actually get it launched.
Omer (07:30.850)
Did you have a bunch of other ideas around that time?
Tony Summerville (07:33.250)
Yeah, and I had tried to do the nights and weekends thing too in my previous job.
So I would spend literally nights and weekends, actually, I would get up really early.
I'm more of a morning person, so I'd get up at like 4am and work prior to going into the office.
And I, you know, I was always interested in real estate, so I had this kind of like rental market thing.
It was not claiming that it was like a precursor or similar to Airbnb, but just I was very interested in the rental market, so I'd worked on that.
But I think one of the things I realized, especially in the last few years of my career before starting Fleety, was like doing the nights and weekends thing.
I know some people can make it work, but it's a lot of effort to get a company off the ground and, and really you need to get out and talk to people and validate ideas.
And a lot of times if you're going to talk to people, you got to do it during business, business hours.
So that's when I sort of realized that if I'm ever going to do it, I got to take the plunge and fully commit to it.
Omer (08:19.690)
Okay, so what was it about this idea that pushed you to committing to this thing that you were then going to quit your job for?
Tony Summerville (08:27.450)
Yeah, well, and to be fair too, like, I had a.
It was probably two or three ideas that I was going to pursue when I quit my job.
And this was, I thought probably had the most.
The most opportunities.
And I didn't really investigate too much any other ideas.
But I think the thing that really got me passionate about it once I started talking to potential customers in the early days was like, like just seeing the same patterns over and over again, the same pain points and the passion for which people sort of were like, yeah, we suck at this, we suck at managing our fleet.
And also just me realizing that there wasn't nobody had built like a modern fleet management software solution.
A lot of the softwares out there were really aimed at like the very large fleet, I think about, like the Pepsis and upss of the world.
But if you looked at the market, when you start doing sort of the total addressable market analysis, there's this long tail of literally hundreds of thousands of businesses like my Dad's that have 50 vehicles and they're not going to go out and spend hundreds of thousands of dollars on old school Software to manage 50 vehicles.
And you also see too, like, okay, the combination of sort of web based or SaaS plus mobile.
You're managing these assets that move around all day.
So by nature these things aren't stationary.
So being able to access data from wherever and do it from a mobile device, like all these sort of things were exciting.
Plus, I've always enjoyed cars and I have two sons and when I was a kid I loved big bulldozers and all that stuff.
So I was genuinely interested in the actual assets that people have.
Omer (09:49.540)
So what stage did you get this idea to before you, you quit your job?
Did you try to go out and do customer interviews and at least some validation before you quit?
Or was it literally like, I need to do this And I've tried to do the day, you know, evenings, mornings, weekends, thing hasn't worked.
I just need to commit and I'm going to then go out and talk to people.
What was the order of events there?
Tony Summerville (10:10.350)
Yeah, it was the latter.
I mean, I had done sort of the nights and weekends research, but I just knew that like in order to really take a swing at this, I had to fully commit.
And, you know, I was lucky.
I mean, I was married and still am to my lovely wife.
You know, we talked about it for several months and this was before we had kids.
It was kind of like one of those things where it's like, timing wise, this is a good time.
Like we could live on her salary and I could give myself a year just to, just to see, you know, if there was really something here and go pursue it.
And so that's what I did.
And you know, you know, worked my tail off for that year especially.
But yeah, I mean, I always tell people one of the hardest decisions was just getting started that day that you quit your job and you're like, what are you going to do?
And you're like, I'm going to go start a company.
And you're like, well, what is the, you know, it's like, well, I'm going to figure all that stuff out.
You feel crazy.
Omer (10:56.490)
Yeah.
Tony Summerville (10:56.890)
But then once you do it and you start working on it and you're quote unquote, living your dream or whatever, like it is so freeing to sort of just actually pursue something.
Omer (11:05.730)
Yeah, I've been in that situation and a number of founders I've spoken to.
It's almost like you're standing at the edge of the cliff, you want to jump, you just can't do it.
You can't stop thinking about it.
And for me it was like, I just need someone just to give me that push and then I'll be okay after that.
But it's just that first getting that momentum.
So tell me about, so you've quit your job day one.
How many customers did you talk to?
How long did it take you to figure out, understand the problem clearly enough so you could start to think about building a solution?
Tony Summerville (11:38.360)
Yeah, so.
And I always, whenever we have about once a month I do like a new hire overview with all the new Fleetio employees and literally show some of the screenshots, like the emails and stuff I would send out to friends and friends of friends, anybody and everybody who would just, you know, sort of connect me with somebody who worked at an organization that had a fleet.
So I spent probably the first three to four months just exclusively doing interviews.
And this was like right around the time that Eric Reese's book the Lean Startup had come out and there was all these sort of like net, you know, new books.
I forgot the other one that was really popular at the time.
So I was creating my like one pager sort of customer interview sheets and then turning that into like these strategy documents.
And it's funny, a lot of the strategy we're still executing on today, sort of the vision was cast in those sort of early months and then, you know, I mean, again I had the skills to be able to at least get something off the ground.
So when I wasn't talking to customers, I was building and writing the initial version of the software.
And then a lot of the customers were, those initial customers were local.
So I'd work on stuff for get sort of features to a point where I would email them and then I would just go visit them and like watch them over their shoulders, like using it and you know, get that direct feedback loop going.
So that was all like the second half of 2011.
So it's technically the summer of 2011 when I left my previous company and it was probably only like a seven month sort of timeframe to all those interviews and getting like an MVP out the door.
I mean I worked a lot and sort of got it to where I was getting the first, especially this first unaffiliated paid customers in that first part of 2012.
Omer (13:06.350)
How many people did you reach out to to try and have these conversations?
And what kind of response were you getting?
Was it like, you know, was it painful enough that a lot of people were responding and were willing to talk?
Or was this, like, did you have to follow up and follow up until people would give you time?
Tony Summerville (13:23.340)
No.
And that was the.
I'm a big, like, signals person, right?
And I'm a big believer in, like, using anything as, like, data points, right?
So if I'm emailing people and they are completely unresponsive or aren't willing to take a meeting, that implies that maybe it's not that big of a problem, right?
It's not that big of a deal.
But I really didn't have a huge problem, like, getting, once I got connected to the right person, that people would take a meeting with me.
I think we're in the south and people are genuinely pretty nice.
And I think I always tell people, like, use that entrepreneur card.
I wasn't trying to sell them anything.
I'm just like, hey, I'm an entrepreneur.
I want to get just some time on your calendar to come in and understand how you're managing your fleet and see if there's some potential pain points there.
And when I would go visit with people, I would just.
I would either literally, like, hear them talk about and describe the problems or see it.
I mean, one of the best examples, and I knew I was kind of onto something, was meeting with a local nonprofit organization and still a customer to this day.
It's called Kid One Transport, and they take underprivileged kids to doctor's appointments.
And they're sponsored by Mercedes.
They have, like, 30 or 40 vehicles.
And I remember walking in their office.
This guy Patrick was the operations manager who managed the fleet.
And he had a whiteboard, and he just had a grid drawn out, and like, that was his fleet management system for those 30 vehicles.
And just getting Patrick to start using Fleetio and going to meeting with him pretty often was really, like, the early days are hard, but you need those kind of like those meetings where you just.
Even if you haven't solved the problem yet, you know that you're working on a problem that is worth solving.
Omer (14:45.720)
When you had people using this mvp, were you charging for it?
Tony Summerville (14:49.240)
I started charging the local customers, like, probably after about three or four months.
I was using a measurement of, like, how often they were using it.
You know, it's.
Even to this day, we measure, like, the health of our customers at the end of the day.
It's like, if the product isn't getting used, like, then it doesn't really have a lot of value.
Right.
And so you can, I think usage is a pretty good proxy for value.
And so once I saw that, like, folks like Patrick were logging in and using it multiple times a week, you're like, okay, they're starting to depend on this.
And then I can remember, like, specifically with them too, like their executive, their executive director controlled the budget.
And I was trying to work through pricing and that kind of stuff.
And I think I was like, all right, this will be $40 a month.
Which farming for nothing was, was, was.
Seemed like a lot.
And they're like, oh, yeah, this, yeah, absolutely, we'll pay for that.
So we have increased our prices a lot over time.
But yeah, this first kind of like beta customers, that was a big part of like, am I ready to, to launch this thing?
Are.
That was directly related to are they willing to pay for it.
Omer (15:47.320)
How did you figure out that price?
The $40 a month, I always knew
Tony Summerville (15:50.720)
in a big North Star of our vision has always been collaboration.
So I knew I didn't really want to do like a per seat or per user model.
It was going to be based on per vehicles.
And then I was just trying to back into a price where it was like a few dollars per vehicle per month where they felt like there was an ROI that was almost like an obvious roi, like they didn't have to really think twice about it.
So that was the.
I mean, it wasn't really like a scientific method or anything like that.
It was just more of like in asking too, like, what do you think?
What would you be willing to pay for this?
And I remember some customers because I was like, all right, this is going to be, you know, $75 or whatever it was, because they only had like 15 vehicles or something and they're like $75 per vehicle per month.
And like, okay.
And you're like, no, no, $75 total for all your vehicles.
And, and so, you know, I think part of it was just like a little bit of trial and error.
But, you know, you're basically trying to figure out if what you have is worth it to them and just trying to dial in that price.
Omer (16:48.670)
And were these mostly face to face conversations?
You said you were spending a lot of time going out and seeing customers
Tony Summerville (16:54.590)
in the early days?
Yeah, absolutely.
Omer (16:56.510)
Yeah.
There's something definitely powerful about giving somebody a price and seeing their reaction, which you don't get online.
Right.
That helps you gauge a lot in Terms of where you are and where the perceived value might be right now.
Tony Summerville (17:08.420)
100%.
Yeah, I mean that, that was, and I'm still to this day a big believer in like getting on site with customers and really having that sort of face to face conversation.
I know it's been difficult the last couple years, but yeah, you just, you can really like your senses beyond just your ears can really perk up and understand things in a live setting.
And then you know, the, the other thing too is like that can then be the basis of obviously like you still want to experiment with pricing, you know, in the digital form.
Meaning like you run different trials or different experiments at different price points or even doing, I forgot what it's called, you know, 295 versus $3 and trying to see if you can boost trials or signups.
So there's definitely multiple experiments.
But I think in the early days, just like having a conversation with people is and seeing their reaction to a proposed price is hard to beat in a digital world.
Omer (17:57.350)
So do you remember how many of the customers who were using the product were, how many of those users did you convert into paying customers?
Tony Summerville (18:04.360)
Gosh, I don't remember exactly.
I mean once, once I realized though too that I mean you also start building the business plan and you start thinking about how does this become a really big business?
Like it was obvious that like we needed to figure out a way to get lots of customers.
So part of it, you know, was there was really two big challenges in that first year is one, can I identify a problem and build a good enough solution to where people are willing to pay for it?
But then two, can I build something at 50 bucks per account?
Like in the early days?
Like you're going to need a lot of customers to be able to build a big business.
So then the second half was like, well, can we build some initial and before the time before it's called product LED growth, but can we build a mechanism to where people can self serve, meaning they start a free trial and upgrade and so on and so forth.
And so once I kind of realized that the problem was there and the solution was like good enough, then it became more of like a focus and attention on like building a digital sort of experience that the value proposition was there, people could start a free trial and then getting unaffiliated customers and starting to really scale this sort of go to market engine was the second really big milestone that I started focusing on.
So I can't remember how many I didn't really because to me the business wasn't going to be successful if I got the first 20 customers that I had been working with for a few months.
And also, like, I'm from the south, like, everybody here is super nice.
I also, like, you're always a little bit concerned.
Like, are these people just being nice to me because I'm an entrepreneur and 50 bucks a month is just.
They sort of feel sorry for me.
And like, I really wanted to make sure that we can start getting customers that have no affiliation to me aren't doing me a favor at all.
Like, I'm literally just solving a business problem they have and they're willing to pay me for it.
And so that's what, you know, I really started to focus on once I got those initial sort of local customers to see the roi.
Omer (19:46.050)
Great.
So from the day you quit your job, it took you about, I think you said six or seven months to get that MVP out there.
How long did it take you to get those first 10 customers?
Tony Summerville (19:55.950)
The first 10?
I think once we launched or once I launched it, I probably got a handful of like unaffiliated customers in the first month.
So like four or five and then like seven or eight the next month.
So within two months probably had 10.
I know we ended up doing a hundred customers in the first year, right?
At 100 customers.
So from January to 2012, got a little over a hundred customers.
And it was around the summertime.
I can't remember exactly how many customers we had, but that was when I made the first hire in the business.
Omer (20:24.630)
Yeah, I want to talk about that because you got to those a hundred customers, but you didn't have anybody else.
It was you just doing everything right.
Tony Summerville (20:30.310)
Yeah, exactly.
Omer (20:32.390)
So do you remember what, what your MRR was when you hired that first employee at the end of year one?
Tony Summerville (20:37.830)
Yeah, we were probably around.
Well, we were probably about a 30 to 40,000 somewhere in that neighborhood of ARR.
So then the bet was like, and we some additional capital that we could put into the business.
But it was like, okay, can I cover somebody else's salary based on our MRR and, and hope that it continues to grow and then sort of be able to build a, a sustainable business.
Omer (21:00.610)
Okay, great.
So you're doing about a few thousand dollars in MRR at the end of year one.
I mean, a hundred customers by yourself as the only person as a solo founder.
I mean, that's pretty good going.
So props to you on that.
Who was your first hire?
Where did you decide to invest that money?
Tony Summerville (21:17.760)
Yeah, so he's actually still with Us.
His name's Matt.
He was somebody I met at like a local kind of startup mixer meetup thing.
And I knew that at that point, like, our problem wasn't necessarily the development side.
It was just like I needed a generalist to help me with everything else.
So sales support, starting to really build a content marketing engine.
And we can talk more about that, but just Matt just did everything other than write software.
Omer (21:42.160)
Okay, so you've got Matt on board, and then I think you year two, you hired what, another three, four people?
Tony Summerville (21:49.090)
Yeah.
So then the next hire was Jorge, who is now our cto.
And at that point it was like, okay, I need to hire somebody that's way better at me than writing software and can focus on it, you know, full time.
Because even at that point, we're.
I'm trying to focus on all aspects of the business and starting to set up initial processes for support and so on and so forth.
So the next two hires were two different software engineers, both of whom are still with us today.
One's our cto, another one's like our principal engineer.
And then I think the next hires were we had a support, a woman who I knew from a previous company that kind of started handling some of the support stuff, other kind of support aspects.
And then, you know, I'm proud to say too, a lot of our first 10 hires are still with us today.
So our VP of marketing, Lori was one of those first.
I think she was one of our earliest hires.
Our VP of sales, Will was like their first, like seasoned salesperson that came in and that I think around maybe higher 8 or 9.
And we have several other people in this first 10 that are still with us today.
Omer (22:45.160)
So let's talk about how you built the growth engine for this business.
It sounds like year one was just a lot of hustling and you doing everything.
Once you see that you're starting to generate revenue, you're putting that back into the business and trying to build a team around you.
I think you mentioned before we started recording that about 70% of your sales today come from inbound.
How did you start getting that going?
Was that really about starting to write content?
What, like, what was the thought process that you went through there?
And how long did it take you to start getting this inbound funnel working for you?
Tony Summerville (23:20.870)
Yeah, so again, I mean that two major things or milestones to get to is like one, sort of defining the problem, building that initial solution, and two, building a go to market strategy that could scale.
And you know, it's funny, like, even the word Fleetio was part of that initial process.
When I first started the business actually was calling it Automate.
So it was like a play auto and then Capital M Mate.
That was a terrible product name from an SEO standpoint because it's just a common word Automate.
And so the initial go to market engine was really built on the back of content marketing search engine optimization.
So being able to and even defining the word Fleetia, I can still remember just looking for words with fleet in it and finding domains that were available.
Fleet IO was actually the initial thing but then our market like didn't understand IO domain so ended up just going to fleetio.com but, but that initial focus was in those, you know, very early days too like building the initial homepage and the product tour and videos.
Like there's still probably videos on YouTube somewhere of like me giving a video overview or a demo that was recorded and just trying to drive leads in the very earliest days.
And then when Matt joined I remember one of the first like true kind of content marketing pieces we created.
And I'm a big like high leverage person, right?
Like if you're going to do something once, how do you leverage it?
And multiple ways and we're still, both of us like are both into automotive so we had a lot of just like general contextual experience with the landscape of how vehicles work and that sort of thing.
But we're still learning as we went about the fleet industry specifically.
And like a good example of us, you know, putting our knowledge or using our research skills and leveraging them multiple ways was like we were building a lot of fuel features or fuel management related features in the product.
We needed to really understand there's specialized credit cards called fuel cards.
And so we were, it was kind of, it's, it's still even to this day a fairly opaque industry.
And so we were doing a bunch of research Internet just for our own good.
We ended up turning a lot of that research into our first white paper called like how to select a fuel card or a fleet card.
And because nobody had really done that before.
And so like that was one of the first sort of evergreen type content marketing pieces that we created that and still we have multi.
We've iterated on that one a lot over the years.
But that those are the types of things that we started building in the early days using research, putting together research that people are, you know, already going to be searching for anyways.
And then they end up on our website and they hopefully start a free trial soon thereafter.
Omer (25:44.530)
Great.
I Just Googled fleet software and you guys come up number one there, like higher than Capterra as well and those sorts of slates.
So that's pretty good going.
But I guess you've been working at this for, for about 10 years, right?
Tony Summerville (25:59.320)
Tell people too.
I mean obviously like you want to do whatever you can to generate revenue as fast as possible, but you know, in this day and age, like one of the things, and even before I started Fleedio that was exciting to me about where the world of like SaaS and really business software is going is like you get to use kind of like consumer marketing techniques in a business sales setting.
And so the opportunity that the Internet has provided all of us is the ability to sort of get our messaging and value proposition out to the masses if you know what you're doing in a fairly streamlined way.
And so from the very early days, I always think about farming.
We're planting those seeds and watering them and at first it takes a while, but if you do it and you're relentless about it, over time that stuff starts to grow and in and of itself becomes a relatively good moat for the business.
Omer (26:49.660)
So year two and three, were you still self funding the business?
When did you raise the first round of investment?
Tony Summerville (26:55.260)
Yeah, so that was four years in.
I mean honestly it was just like we're just so heads down and focused on building a good business and being capital efficient, so on and so forth that I don't really think too much about.
And I was probably naive, but just didn't really think a lot about fundraising and developed some really good relationships with some mentors, particularly one that had built some very successful based businesses in Birmingham, Alabama where I live.
And in 2016 he was the primary investor.
And at that point it was like the business was going really well.
We're really truly capital constrained.
Like I wanted to hire more people.
And the beauty of software as a service and recurring revenue is you get that recurring revenue.
The challenge is that you have to find you don't have a lot of capital up front oftentimes.
And so that that first round of 750k really enabled us to hire ahead of revenue for the first time.
Omer (27:40.830)
So the other thing that other than content marketing, a sizable chunk of your revenue also comes from outbound sales.
Now how did you build that out in the early days?
Obviously year one and two sounds like you were doing most of the sales.
You hired your first salesperson year two.
And then how did you build that team out?
How did you grow sales and how did you figure out how much of your time you're going to spend in doing some of these things like inbound and paid advertising and investing in sales.
So was this really just trying a whole bunch of things or was this like, what was the growth strategy in the early days?
Like, how did you figure out where to invest the money that you had?
Tony Summerville (28:18.350)
Yeah, I mean, it was really all inbound, but using primarily channels like SEO.
So just continuously building for the long tail.
The nice thing about the fleet management or the automotive sector is there is like a long tail of searches that are applicable.
So then it just becomes writing blog posts and writing content that you'll hopefully end up on a keyword for something that relates to what you do.
And you can gather website visitors that way.
In the early days too, I mean, started using Google AdWords and Things of that nature, I think because we were bootstrapped and always needed to be extremely capital efficient.
Like we built a lot of the really important, like measurements of ROI and CAC and payback period and all those things for all these different channels, especially the ones we have to pay for, like Capterra and like Google AdWords and all those types of things pretty early on.
So we didn't have a lot of money to burn and be wrong about those things.
So we had really good systems in place from.
From the early days there, really outbound, we didn't.
It was more focused on inbound for a long time because that was working and there was just this huge ocean of possibilities there.
And we could see too, like we were capturing.
You monitor all the ratios, right?
Like, how many unique website visitors are you getting?
And is that growing month over month?
But then are you also able to, you know, grow the percentage of those that you actually convert into a lead, and then of those ones that are a lead, how many of those convert into a paying customer and so on and so forth.
And it was clear like there was and still is to this day, I mean, lots of room for improvement in just the inbound funnel.
I don't think we really started focusing on outbound till well north of 10 million in ARR.
At that point, you're sort of thinking like, okay, how are we going to get to 100 million?
And you start sort of thinking about like, well, what are the channels that we're going to have at 100 million that we need to start developing today?
And outbound was always one of those things.
It's a huge ocean of, of potential customers.
And like, if you rely on everybody to do some Google search to come and Find out about what you have to offer.
Like you're just, you're going to miss out on a lot of opportunities.
So we had to build, but building an outbound sales team took some trial and error.
It took finding the right leader to really build that team.
And you know, and then it takes time too.
It's not like a three month thing and all of a sudden it's working and you're like, oh, that was a good investment.
I mean it definitely takes some trial and error and time to get it right.
Omer (30:25.170)
So what did the funnel look like in those first few years?
So you're getting a lot of inbound traffic, which is great.
So the investments that you're making in SEO content marketing is slowly starting to pay off.
And then what would happen?
Would people just request a demo and then your sales, you know, person would pick up from there and try to convert them?
Or were you driving more towards, okay, this kind of product led growth model?
You know, can we build more of a self serve model and get these people to onboard themselves?
Tony Summerville (30:53.800)
Yeah, the original like our primary focus has always been driving trials because if you get somebody in the product, you know, in theory they can instill this day self close.
Right, like, or self become a customer without needing to talk to anybody.
I think when we were in the before having a larger sales team, like it's, if you have a lot of like leads, you need to have enough sales capacity if you're gonna drive demos to be able to actually conduct those demos.
And so in the early days, like if you were to go back and look at our website, a lot of like the calls to action were start free trial.
Now it's a mix of both and we do have a lot of calls to action to request a demo.
But now we have a team of people and we will respond to that demo request within a couple of minutes, if not seconds.
And we have inbound sales development reps that will email you and call you immediately and then schedule a time for.
And we have a huge team of account executives.
And now today it's all structured, we have different departments, SMB versus Mid market versus enterprise.
But in the early days it was just like account executives and we only had a few would get assigned any lead.
It didn't matter if they had 10 vehicles or 10,000 and they would just get assigned the lead and they would just follow up with them when they could.
And that again goes back to like why raise money?
Well, it's like it's starting to work.
You can see it in the Numbers and it's like we need to hire more people to be able to handle the demand.
And in my opinion, that's when you should be raising money, is when you know you've got a good use for it.
Omer (32:18.310)
So at some point you decided to build a second product.
Can you tell me about that?
When did that happen?
What was the driver?
Tony Summerville (32:23.350)
Yeah, and that was probably one of the larger mistakes looking back that we've made over the, that I've made over the last, over the last decade of building Fleetio.
And so what I sort of thought, and this was me sort of not doing enough customer validation, was that we've got this now fairly large customer base that's managing their assets.
We want to manage the drivers too.
And in the fleet world, driver behavior, how good of a driver are you, how safe are you?
Is definitely a big deal.
And traditionally there's a huge industry of traditional GPS and telematics devices that are plugged into the vehicle.
Now vehicles come off the assembly line with proper equipment, modems and all that stuff inside.
But historically it's always been like an add on piece.
And then those things track every trip, you know, how the vehicle's being used.
Well, we wanted to build something and we ended up calling Fleetio Drive.
That would use your cell phone and basically be running in the background.
It would detect automatically when you started a trip just based on the motion of the phone and all that stuff.
And then it would also really track all the different aspects of how you were driving.
So hard braking, rapid acceleration, hard cornering, all those types of things and then come with a score.
So we called it Fleet Air Drive.
The problem was that one, we took our off the ball of what was working at that point.
So the core platform was really growing and it was like, okay, let's go and build a second product that we can sell into the base and have two things.
And the long story short is that we spent a lot of time building the second product, it and it was tough because it's not like it had no success.
It had some success, which makes those types of things harder to kill because it wasn't a complete flop.
It also wasn't just like a knock it out of the park home run.
And so, and it really was a couple of years of effort before we finally just decided to shutter it and get back to focusing on the core platform.
Omer (34:00.900)
How did you make that decision to shut it down?
Because like you just said, if you make, if it's a clear failure, that's an easy decision.
But when you're, you're seeing some signs of life and it feels like that there is a potential opportunity here.
It's a tougher decision to make.
So what led to you deciding to shut this down and then what was your thought process?
Tony Summerville (34:21.389)
One of the things that we've done for a long time is had quarterly strategy off sites with like the leadership team and then a handful of other folks too, that are kind of part of this broader strategy team.
So at the beginning of our quarter, in fact, we're doing it next week for off site.
So we've always had this cadence of like these larger, you know, big strategy sessions.
And starting the Fleetio drive product was a couple of quarters of discussion.
It was like, all right, we pulled the trigger and went after it.
And then building up to any of these strategy meetings, everybody, and for whatever sort of division or department of the company they represent, they write these briefs of like a synopsis or a summary and a lot of metrics and things like that related to what their sort of scope of the business and how it's.
And it was sort of a couple of different strategy meetings where it's like, okay, this isn't growing like we hoped.
So the revenue wasn't there as far as like what our expectations were for success.
And then I was also clear too, like, this was a much harder product for us to scale from a support standpoint because, I mean, it was buggy.
You're now dealing with drivers, like trying to write in or call into a support team, be like, it's not tracking my trips.
So.
And then like diagnosing a problem on mobile is still hard to this day.
It was even, you know, like back then it was, this is four years ago now.
I mean, it was just, it was a support nightmare and the revenue wasn't there.
And so I mean, it was just a data driven decision at the end of the day.
And then it became like in those strategy meetings, we decided to kill it.
And then it becomes like, oh, how do we offboard all of our customers?
We're not just gonna pull the plug on em overnight.
I mean, there was one large customer that had like hundreds and hundreds of drivers on it and so they depended on it.
And so it was probably a nine month process, maybe six months to them find them a landing place for a different system for them to put their drivers on.
So yeah, it was a process, but I think the strategy meeting cadence causes at least four times a year these like, deep reflection on how the business is going.
And that's been a Huge, like heartbeat for the business for a long time.
Omer (36:12.180)
Yeah, it's great that you do that.
And I think a lot of times when founders think about strategy, it's to figure out what are the things that I should be doing.
But often strategy is really about what are the things I say no to.
And that's really hard to do.
But I do like the idea of this regular cadence just to make time to just step back and reflect on what's going on.
Because I think all of us could do that a little bit more.
And it's when you pull yourself away, you can, you can see a little bit more with clarity in terms of what's going on and make some of those decisions.
You decided to quit your job and give this thing a try for a year.
You're now in a position where you've got a successful SaaS business doing eight figures in ARR.
A team getting close to 200 people raised 25 plus million dollars.
When you started on that first year, where were you hoping this business would get to?
Tony Summerville (37:04.490)
Oh man.
I mean, thinking back, I knew like especially six to nine months in, I was like, okay, this can be a solid business.
And I can remember like thinking too.
And I was my own personality and everything.
I much enjoy the kind of details and the building aspect of everything.
So I always even assumed too, like, I may not want to like, I don't know.
The biggest I could think about is like running a 50 person company which just seemed huge when we were 5 or 10 people.
I think what.
As time goes on, my hopes and expectations have risen over time.
And now, I mean it's in the early days, it's hard to imagine even getting to a million in ARR.
And then you sort of get there and you're like, okay, 10 million's in sight, right?
And then you hit 10 and you're like, Gosh, we could get to 100 and well beyond that.
And just like, so you sort of hit these milestones and then you start thinking about the next one.
And so in the early days, I definitely didn't think we.
I didn't, I guess I hoped, I didn't certainly like think it could get as big as we've gotten to today, but in a lot of ways too.
I mean, I hope that if we catch up in a few years from now, we're much, much bigger than we are today, so I know we can get there.
Omer (38:14.530)
Was this the first kind of real business you'd built?
I know you mentioned you were trying to build businesses on the side but were you just really in the 9 to 5 before you committed to this?
Tony Summerville (38:23.810)
Yep, totally.
I never founded anything or started, you know, a real company other than this one.
Omer (38:28.480)
And how much help did you get from your dad and kind of his experience of building a business even though it wasn't a software business?
Tony Summerville (38:35.440)
Yeah, I think what I got from my dad was just like growing up and my dad was the founder and owner of very successful and growing business and just sort of seeing one his work ethic.
Like, I know he worked a lot and still does this day, but he enjoyed it.
Like he was passionate about it and still is.
And so I think what I saw is just like the work ethic that it takes to build something successful, but also like, pressure's not the right word, but just the opportunity you have to really affect a lot of people's lives.
I mean, his business has hundreds and hundreds of employees.
And then you think about all the families and things like that are sort of affected by the decisions that you make.
You just sort of.
You see people handle that and really lean into that opportunity.
And I got to witness it firsthand from my dad and both my granddads also had fairly successful businesses when they were alive too.
And it's just behind the scene peak of like how they act and how and operate and the respect that they garner from the community.
Always looked up to that.
Omer (39:30.790)
Awesome.
All right, we should wrap up.
We're going to go into the lightning round.
Got seven quick fire questions for you.
Just try to answer them as quickly as you can.
Tony Summerville (39:38.070)
Awesome.
Let's do it.
Omer (39:39.510)
What's the best piece of business advice you've ever received?
Tony Summerville (39:42.150)
This one's tough.
I mean, I tried to think about any sort of one piece of advice or one snippet of advice I could share.
I mean, a lot of it is so stage dependent.
I think the biggest thing that I've learned directly and indirectly too, from a lot of my mentors is just really take care of yourself first and foremost.
Your own health, your own family, your own relationships.
Like the important things in life, you got to take care of those first.
And then you can build a great business on top of that or a career on top of it.
And so I guess one of the mantras I've always had is, and heard this from other people is like, focus first and foremost on your eulogy, not on your resume.
Omer (40:14.680)
I like that.
What book would you recommend to our audience and why?
Tony Summerville (40:18.040)
My favorite business book is Shoe Dog about Phil Knight and the founding of Nike.
I think it's Just the most fascinating story about one of the most iconic companies in our sort of time.
Omer (40:28.680)
What's one attribute or characteristic in your mind of a successful founder?
Tony Summerville (40:33.080)
Curiosity.
100%.
I think anybody and everybody that I've seen that's built a business from the ground up has been genuinely curious about things, all aspects of business building, whatever market or customer base they're serving.
You have to want to dig into the details, you have to want to interview people.
You have to be just naturally curious and ask great questions.
And I think curiosity is just like the sort of basis of all that.
Omer (40:55.830)
What's your favorite personal productivity tool or habit?
Tony Summerville (40:59.030)
So a big thing we do at Fleetio, and I preach this to every new hire, is we do a daily check in or daily standup.
I always tell people it's good obviously to keep your team informed or the direct sort of coworkers that you work with every day.
But the big reason we do it is in the productivity hack is I call it starting your day on offense, which is just taking 30 seconds or two minutes or whatever to think about what you want to accomplish that day.
Put it into writing.
Here's what I'm going to do today, here's what I did yesterday, here's where I'm going.
Blocked, whatever.
But you know, the reality is if you spend just a few minutes thinking about what you want to accomplish every day, that's how you sort of move the ball forward on the important things.
Omer (41:32.460)
What's a new or crazy business idea you'd love to pursue if you had the extra time?
Tony Summerville (41:36.060)
You know, I, I don't really spend a lot of time thinking about new ideas.
I think, you know, if I were going to chase some passions of mine with a net, new business I still really do love like real estate and architecture in particular.
So probably I don't know what it would be.
I have no idea.
But you know, pursuing that industry specifically in the automotive world or landscape, I think a crazy idea would be, and I don't even know if anybody's working on this, probably are, but just trying to figure out how we take sort of traditional ownership of vehicle like the title and sort of put that on the blockchain I think would be interesting.
So I don't know, it's a couple ideas.
Omer (42:06.960)
What's an interesting or fun fact about you that most people don't know?
Tony Summerville (42:09.840)
I was a pretty accomplished swimmer growing up and it probably gave me a lot of my own sort of push to make myself better every day because you're really just competing against yourself and trying to better your times.
But when I was 10, that was probably when I.
Because I'm not that big.
A lot of the best Olympic swimmers, they're all pretty big guys, but when I was 10, I was ranked fifth in the nation in 100 freestyle.
Omer (42:30.060)
Wow.
And finally, what's one of your most important passions outside of your work?
Tony Summerville (42:33.820)
So I have a great family, two boys and a lovely wife.
And we're lake people, so we spend as much time as we can outside of on the weekends, especially in the summertime, up at our lake house on Smith Lake.
Omer (42:46.700)
Nice.
Tony Summerville (42:47.510)
Great.
Omer (42:47.750)
Well, thank you, Tony, for joining me today and sharing your story.
I think it's always, you know, great to talk about where you are today and how you've been able to scale the business, but I think, equally importantly, it's great to cover those early days and sort of talking about the first year and doing everything by yourself.
And I know that's not always the easiest thing to remember.
I mean, I can't remember what I had for breakfast yesterday.
So thank you for, you know, racking your brain and helping us understand and share that story.
Now, if people want to find out more about Fleetio, they can go to fleetio or fleetio.com and if folks want to get in touch with you, what's the best way for them to do that?
Tony Summerville (43:25.330)
Yeah, I mean, I'm more of a lurker on Twitter.
I'm Somerville, but I really don't tweet that much.
But if anybody wants to just ping me via email, it's just Tony.
T o n y pleadio.com thank you
Omer (43:36.010)
so much, and I wish you and the team the best of success.
Tony Summerville (43:38.930)
Thanks for having me today.
Enjoyed it.
Omer (43:40.450)
My pleasure.
Cheers.
Tony Summerville (43:41.650)
Cheers.
