1 year in he had just 3 customers—today he’s at $100M ARR. | Forrest Zeisler, Co-Founder of Jobber | Forrest Zeisler, Co-Founder of Jobber

Forrest Zeisler spent 6 months hearing “no” from every potential customer he spoke to. One year in, Jobber had just three customers—paying $29/month. Today, Jobber generates over $100M ARR, has raised $180M in VC, and employs nearly 1,000 people.

In this episode, Forrest shares the brutally honest story behind Jobber’s early days: months of rejection, maxing out credit cards, and nearly quitting. You’ll learn why there are rarely any “silver bullets”, how he handled relentless investor skepticism, and how incremental daily improvements—not crazy inflection points—led to exponential growth. 

If you’ve ever wondered whether your startup can make it through the grind, this is a must-listen.

Why You Should Listen

• Learn how to persist through brutal rejection—Jobber took 6 months to land their first customer.

• Understand why chasing “silver bullet” features or channels rarely works.

• Find out when it makes sense to keep going despite extremely slow traction.

• Hear why your first investors can shape or destroy your startup journey.

• Discover why “compound growth” beats chasing short-term inflection points.

Keywords

product market fit, startup growth, founder stories, fundraising, bootstrapping, Jobber, vertical SaaS, early stage startups, scaling startups, startup rejection

(00:00:00) Intro

(00:01:55) From Freelance Devs to Startup Founders

(00:07:23) Six Months of Rejection

(00:15:09) Landing the First Customer and Almost Losing Hope

(00:25:39) Brutal Investor Feedback and the $250K Seed Round

(00:35:13) Early Growth and Near-Death Experiences

(00:44:15) Hitting Customer Milestones and Finding True Product Market Fit

(00:48:41) Crossing $100M ARR and Key Lessons Learned

(00:51:11) When to Quit and When to Persist

Chapters

• 1:56 From Freelance Devs to Startup Founders
• 7:23 Six Months of Rejection
• 15:10 Landing the First Customer and Almost Losing Hope
• 25:39 Brutal Investor Feedback and the $250K Seed Round
• 35:13 Early Growth and Near-Death Experiences
• 44:15 Hitting Customer Milestones and Finding True Product Market Fit
• 48:41 Crossing $100M ARR and Key Lessons Learned
• 51:11 When to Quit and When to Persist

Transcript

Forrest Zeisler (00:00:00):
We've never come across some silver bullet feature that changed anything. We've never stumbled across some silver bullet marketing channel that changed everything. It's if you look at our charts, you won't see a single inflection point, just a slow, steady exponential curve of every day being 1% better than you the day before. But that compounds so that last month we made more new customers than we did in the first seven and a half years of the business put together in one month. Even though we kept hearing no, the reasons were never insurmountable. All the reasons were often about. Feeling or nuance, but technology could cover them, right? No one was saying they didn't need our solution. They were all saying they didn't believe that our solution was going to be the right solution. We went for six months, every couple of days, talking to a business, showing them our product, and hearing the word no. Never raise money from anyone who, you wouldn't have over to your parents' house for dinner. Really simple advice. It was fantastic. It helped us connect to the fact that these are partners, right? Like it's a marriage. You're not just taking the money and ignoring them. And you want to find somebody who's bringing a lot more than just money to the table. Just under 1,000 employees. We've raised $180 million in venture capital, USD. And we're continuing to just compound that. How do we get a little bit better every single day?

Pablo Srugo (00:01:17):
And as you said, well beyond $100 million top line, which is probably the most, for me at least, always the revenue metric.

Previous Guests (00:01:22):
That's product market fit. Product market fit. Product market fit. I called it the product market fit question. Product market fit. Product market fit. Product market fit. Product market fit. I mean, the name of the show is product market fit.

Pablo Srugo (00:01:34):
Think back to the last few months, the last few years, as you've been running the startup. How many different founders have helped you out? The reality is founders help each other out. That's just who founders are. They pay it forward. So help a founder out. Take literally five seconds, take your phone out of your pocket, and hit five stars. Forrest, welcome to the show. It's a pleasure to have you here.

Forrest Zeisler (00:01:54):
Thank you for having me.

Pablo Srugo (00:01:55):
Dude, so I mean. The beginning of Jobber, we're having a quick conversation as I normally do before. And there's some pretty interesting, fascinating stories in the early days of Jobber, which was a while ago. I mean, now you've raised like $180 million. You're quite a big company today. But 14 years ago, as I understand it, you were just two kinds of developers playing around and building random things. So, I mean, take us back to that time. How did, I mean, how did you meet Sam, your co-founder? How did things kind of start and then get off the ground?

Forrest Zeisler (00:02:28):
Absolutely. Yeah. The world was a different place 14 years ago. Simpler times. Yeah. Neither Sam nor I knew each other actually at the start of all of this. We were both freelance developers. And that meant we went around talking to small businesses all day, trying to understand their problems, trying to convince them we could solve them with technology. And every so often somebody would say yes. And we quickly whip out. Back then, that was usually WordPress websites, if we're being honest. Every so often, we got something a little more interesting. But we solved their problem for them, shipped it out, and then moved on to the next client. That was a really formative experience. I found I really loved it because you got to meet people and talk to them in person. You got to understand their problems, solve their problems, and then you got to see the look on their face when you had built something right. You also got to see the look on their face when you built something wrong. It was a really good experience. You'll learn how to be really customer obsessed, and you feel like you're making a difference. Freelance developers, you know, tend to work out of coffee shops. Very common scenario. Pay your rent one coffee at a time. And I kept running into, you know, the same faces day after day at different coffee shops. And one of them was Sam. Doesn't take long to, you know, start to recognize each other. You both know that you're there coding black screen, colorful syntax. Like it's obvious that we're both there doing the same thing every day. So start making small talk.

Pablo Srugo (00:03:58):
And where was this, by the way? Like what city?

Forrest Zeisler (00:04:00):
This was Edmonton, Alberta. And the spot where we ran into each other the most was the Remedy Cafe over on 109th Avenue.

Pablo Srugo (00:04:06):
What was the developer community at that time in Edmonton, Alberta? Was it the two of you or just?

Forrest Zeisler (00:04:13):
It was mainly a freelance community, small dev shops. There were a bunch of people. Then there were two big ones, BioWare. came out of Edmonton, Alberta, and Intuit had their QuickBooks Online international division. So that was about 300 people. I was pretty disconnected from those communities. What we really had was a small startup community. Startup Edmonton ran demo camps. People would show up once a month, show off fun things they were working on, neat ideas they had. But there wasn't an established community of real companies. There wasn't a pipeline of venture flowing through Edmonton, Alberta, back then. When Sam and I, you know, we used to make small talk. We'd talk tech. We'd talk customers. And the one day, it was a Friday, and he was telling me about some work he was doing for a local window washing company, helping them build some things that were very, like, tailor-suited to their internal operations. But it gave him a chance to look under the covers, and he was seeing, like, wow, every part of this business would benefit from more technology, better systems, better processes. And it got him sort of pattern matching and thinking about some of the other businesses he talked to over the years. He was mentioning this to me, and I got very excited because just a couple of weeks earlier, a friend of mine that worked for a painting company had approached me asking if I knew any software that could help them with their problems. Here we had it. Two different businesses, two different industries. Same sets of problems. And we had both already looked and knew there weren't any good existing solutions. And that was, 

Pablo Srugo (00:05:45):
What were the main problems? Like from the customer's perspective, what was the thing they were coming to you for?

Forrest Zeisler (00:05:49):
Honestly, back then it was like a lot of lightweight CRM. How do we keep track of all the details of the different properties? Some basic invoicing, basic scheduling. Like these weren't hard problems. These were established, but no one had put together the pieces in a way that really made sense for home service businesses. Also, 14 years ago, there wasn't the plethora of online software that there is today. The iPhone 3G had just come out. In fact, I don't think it was even out yet when we had started this. There wasn't an app store yet. BlackBerry was the predominant mobile operating system. You know, a painter isn't going to go sign up for Salesforce. So we started getting this idea that there might be something here. Now we had not connected the dots on the scale of this opportunity. I want to be really clear. Like we weren't like, we're going to make a, you know, billion-dollar business in this space. We were still thinking about like freelance developers, like contractors. Hey, we could, you know, instead of solving all these problems from scratch each time, if we make a bit more of a generic solution, we could really quickly adapt it to businesses. I bet we could sell hundreds of these. We thought it would be a nice tailwind on our freelancing. And we actually put it on a piece of paper as we were brainstorming and thinking about our aspirations for the business that our goal was to hit $8,000 of monthly recurring revenue. 3,000 for him, 3,000 for me, 1,000 for the servers, and 1,000 for marketing. It would be a really nice revenue stream to supplement our day jobs. We hadn't quite realized what we'd stumbled upon quite yet.

Pablo Srugo (00:07:23):
You were both working full-time elsewhere as you did this freelance stuff?

Forrest Zeisler (00:07:26):
No, we were paying our bills with the freelancing. So we started to stumble on this idea. It felt like there was something there. We didn't quite understand it yet, but we started chipping away evenings, weekends. We build a clickable prototype. It's smoke and mirrors. It doesn't actually work. But if you click on it in just the right sequence, it pretended to be a good product. And we just started getting in front of businesses. We really quickly exhausted the five or six that we knew.

Pablo Srugo (00:07:51):
What did you build in your prototype? Like basically, you know, somebody calls into your painting company, you add them to the CRM, you schedule an appointment, these kinds of features, you invoice them when the job is done.

Forrest Zeisler (00:08:01):
Yeah. It had a CRM built a little more around properties. Cause again, that was a big thing for home services. You're driving out to the property site, and a client might have multiple properties. But service addresses are first-class citizens when it comes to home services. And that was something that was missing from a lot of the CRMs back then. It had very basic invoicing. It had very basic scheduling. And one of the more novel things was it was very configurable for what kind of information you could store against the property. So if you cared about, how many bedrooms or if you cared about gate codes, instead of generic note fields, you could personalize and customize the information it was storing. But again, this is nothing groundbreaking. You're not winning any innovation awards by doing this. We just took pretty straightforward patterns that we were all familiar with and combined them in a way to solve the problems for a customer base that had been getting ignored. We quickly went through the first five or six businesses that we knew. And then before you know it, we were just cold calling out of the phone book. We had a whole little script put together. Hey, I'm not trying to sell you anything. We don't even have anything to sell. We're just two guys working on a product that may someday help businesses like yours. You're an expert in your field. If I could grab 10 minutes of your time and show you what we're working on, I'd really appreciate any feedback you could provide. Do I understand your business? Are we working in the right direction? Or am I completely wasting my time here? And of course, when you're reaching out and treating people with respect. Treating people like professionals, they're often really generous with their time. We got a lot of hang-ups, a lot of, you know, swearing. Once every day or two, we got a yes. And we drive out to their job site, and we take out our laptop, and we click through and give them the demo of what we were working on. And every time we'd end the demo with, "So is this something you'd use for your business?" And every time they'd say no. But then we'd ask why? Right. That's a really important question for an entrepreneur asking why. And they'd explain to us how we missed the mark. Why they didn't have faith that our solution was going to be the right solution for them. And we take that feedback. We go back to our coffee shop. We continue to iterate and tweak on the product.

Pablo Srugo (00:10:08):
You remember anything specific from those days, like anything somebody said, that maybe. I know it's a long time ago, so you might not. But like something that resonated or stuck.

Forrest Zeisler (00:10:17):
The flexibility in scheduling, how the invoice and work, just really the lack of comfort with using technology. To solve the problems. It was funny. No one felt they had control of their businesses. Everybody was describing very similar problems, right? Like, you know, scheduling is a headache. Keeping track of employees is a headache. Staying on top of your billings is a headache. Like, no one felt these things were working well, but everybody actually really liked their systems. Like they had filing cabinets and folders, and it's like they weren't willing to change. Like, no, no, don't like, what are your problems? Oh, we can't figure out scheduling. Well, do you want to try our scheduling? No, no, I got this calendar. It works fine. Right? And it was funny because we went through all of these conversations. And even though we kept hearing no, the reasons were never insurmountable. All the reasons were often about like feeling or nuance, but technology could cover them, right? No one was saying they didn't need our solution. They were all saying they didn't believe that our solution was going to be the right solution. I heard a quote. I don't know who to credit for the quote, but don't fall in love with solutions, fall in love with problems. And every conversation we had with customers validated that this problem was bigger and more important than we had realized. We went for six months.

Pablo Srugo (00:11:31):
Wow.

Forrest Zeisler (00:11:31):
Every couple of days, talking to a business, showing them our product, and hearing the word no.

Pablo Srugo (00:11:36):
And was it a case of them, you know, because people like the danger path, obviously in your case, whatever happened and we'll find out, let the success, but. The danger path is where you get into this like, oh, one more feature, one more feature, you know, like, but that it sounds like that's not really what you were hearing. Like they were saying, maybe if you're out of this feature, then it would be interesting for us. There was just almost like a fundamental disconnect that I'm still trying to understand exactly what it was.

Forrest Zeisler (00:12:02):
It is so dangerous to go chasing features. A really important thing is having a vision for where it's going to end up and anything that people are asking for that is on the path that you had previously envisioned. That youth is like, wow, that makes sense for 80% of the market, right? Everybody is going to need that. Let's build it. But if they're asking for something like it's really unique to their business, if they're asking for something that takes it in a different path, a decade from now, you're a different business than you would have been. You got to say no. To be very clear, through all those conversations, there were lots of things we were asked for that we ignored. But every piece of feedback was a discussion that Sam and I had. And I don't know if we had good instincts or got lucky on what to say yes to and what to say no to. We were really nervous on going down in a weird direction, getting distracted. We'd be living in the service world, solving problems one customer at a time and building things that could not then be used by another person, another person. So maybe that was it. Maybe we had developed instincts on knowing when we were building something that was tailored to an individual business and when we were building a product that many people would be able to buy.

Pablo Srugo (00:13:11):
And was there, like, six months is a long time of hearing no's. Was there a point where you looked at Sam or Sam looked at you and was like, "Listen, there's nothing here. Let's do something else."

Forrest Zeisler (00:13:21):
Yes. So two thoughts on that. One is, through all those conversations, as I said, no one ever convinced us that the problem we were solving wasn't an important problem to solve. So if we'd been going out and talking to people and discovered that there wasn't a market, I think we would have bailed out earlier. But the more conversations we had, the more convinced we were that there was a market here. We just hadn't figured out how to tap into it yet. The second thing I think is that we had each other. I have an unbelievable amount of respect for solo founders. I know I could not have succeeded as a solo founder. When I think about the number of times over the last 14 years where I was ready to throw in the towel and Sam was there talking me out of it and vice versa, where he's having a really bad day and I have to be the optimist and like, come on, we're going to get through this. We could figure it out. Like being a founder is a huge emotional roller coaster. And when you have a partner, odds are one of you is up while the other one's down. And that really, really helps to sort of balance out those emotional swings.

Pablo Srugo (00:14:26):
So walk me through then. At month six, do you think start turning around?

Forrest Zeisler (00:14:32):
Yes and no. We were meeting Graham from Painters Enterprise for lunch. When we called him up, he could tell we were starving entrepreneurs. Like, we had no money, but he was a fantastic guy. He was so generous, and he offered to take us for lunch. So we grabbed some lunch, and we were showing him the demo. And when we asked that faithful question, would you use this for your business? He said, "Yes." And of course that caused his own panic because you got to remember the product wasn't actually a product yet. It was a smoke and mirrors demo. We were like that proverbial dog that is chasing the truck. When you catch it, you don't know what to do.

Pablo Srugo (00:15:09):
But so through that time you hadn't, because a lot of people would have used that time to just build out the product kind of in parallel. You guys didn't really do that?

Pablo Srugo (00:15:16):
No. We were chipping away. So it was more of a product than where we started, but we were constantly tweaking and adapting. And we were still doing a lot during the day. Like we still were doing some freelancing on the side to help continue to pay the bills. We were bootstrapped, not funded. But around this point, we get our first yes. And we tell them, we will have the product ready for you in three weeks. And we just go heads-down coding, completely focused on this. About four weeks later, we had our first user using our system. And it felt great. We were like, "Yes, we have product market fit." We were so excited. What we hadn't really realized was that we went from a product that 100% of people say no to. To a product that 99% of people say no to. Because the very next day we started making calls, and we were back to no, no, no. We continued to take the feedback from now our first actual user, seeing how they were using it, seeing how they were experiencing it, and the ongoing stream of no's we were getting. Three months later, we had user number two. We got our next yes. Two months after that, we got our third yes. Now, here we are a year in, and we have three users paying us $29 a month. And at this point, we're also all in. We've dropped all the freelancing and side hustles. We're deep in credit card debt.

Pablo Srugo (00:16:33):
I was going to say, where's the money coming from?

Forrest Zeisler (00:16:36):
Our servers are being run off my wife's credit card. She was the only one with a job amongst us. And we hit that point of desperation where we go to our parents and do a friends and family round, which is really just a grown-up way of going and asking your parents to help pay rent.

Pablo Srugo (00:16:54):
That's right.

Forrest Zeisler (00:16:55):
Like you sell them some shares, you know, in air quotes to it, really, like they know the deal. They're just helping bail their kid out of. Because we need the money. But they go along with it. So we raise a friends and family round.

Pablo Srugo (00:17:10):
How much did you raise? Like $50K, $100K?

Forrest Zeisler (00:17:12):
No, like $25,000.

Pablo Srugo (00:17:14):
Okay. Literally just pay my bills.

Forrest Zeisler (00:17:18):
And put it all in a bank account. And then Sam and I just took $2,000 out each month to help cover our bills. Like we didn't know anything about accounting or payroll. Like it was chaos. That'll come into the story a little later. But we were starting to get a little bit of traction. Three customers doesn't sound like traction. But we could feel a slow, steady changing in the momentum. It took fewer no's to get to the next yes. Every time we were reaching on talking to people, they sound a little more interested. They asked a few more follow-up questions before they said no. Their eyebrows showed engagement, right? Like, you know when you're having a good conversation or bad conversation, and they were getting a little bit better, a little bit better, the more we worked on this. We'd also started doing a lot more promotion of our product online. Now, again, we had no budget. We had no money. So we were just doing the old-school guerrilla tactics, going into forums, trying to stir up some interest. One of the forums that we had a lot of early traction with was one called lawnsite.com. It's just a forum for landscapers, primarily Southern US. It didn't take very long for the moderators of that forum to spot us and go like, "Hey, you guys, you're not actual landscapers. You can't be in here promoting your product." We'd also been very respectful through the whole process. We weren't pushy sales. We were asking a lot of questions, trying to contribute to the threads, not just promote our stuff in threads. And we talked to them. They saw our situation, took pity on us, and actually created a brand new marketing tier. For the smallest, you know, like, 10-pixel-by-5-pixel style ad. It's stuck in the very bottom corner of their forum just to make us advertisers. I want to say it was $200 or $250 bucks a month. It was something very low, but this allowed us to be advertisers, which then let us engage with people on the forum. This and other opportunities were starting to drive more traffic to the website. And again, people were signing up. They were checking out the trial. They'd spend longer in the trials looking around before they ultimately abandoned it. Like we hadn't got there yet, but every month things were a little better than they had been the month prior. It was right around when 37 Signals had launched their book, Rework. It was all about generating that flywheel of word of mouth. You build a great product, those users will go tell everyone. That will attract more users, who will then spread the word more. And we got into our headset. We just needed a little bit of cash infusion, a little bit of money to help seed our product with our first group of loyal customers. And then they would go spread the word. That logic was a little flawed. I'm not saying that was the right thing to do.

Pablo Srugo (00:19:59):
And you still had just the three customers at that point?

Forrest Zeisler (00:20:02):
At this point, we still had three customers. After spending a year to get to three, three felt like a large, loyal base. So we made a plan to go raise $50,000. Again, Edmonton, Alberta. No one raised venture capital out of Edmonton, Alberta. We did not know what this meant. We didn't know how to go about it.

Pablo Srugo (00:20:18):
This is what, like, 2011 or something like that?

Forrest Zeisler (00:20:19):
Yeah, exactly. So we put together a plan. It's truly one piece of paper, double-sided, to raise $50,000 to do marketing. We threw some numbers that we had kind of made up on their just best guesses. The numbers include things like our customers would pay us $29 a month. We estimated it would be about $100 in advertising to attract a new customer. And we started shopping this plan around to anyone we knew with money. Throughout this process, again, we started getting a lot of no's, but I knew about one venture capitalist who was an alumni of my fraternity. Back then, again, I was very naive. I didn't understand that there were different types of venture capitalists. This guy, he does gyms. He does restaurant franchises. He invests in brick and mortar stores. Like it's a completely different business. But I didn't understand or appreciate that distinction back then. I just reached out and be like. And tried to. I tried to play it cool. I was like, "Hey, I'm working on raising some money. I know you're a businessman. I'd love some advice." You know, send him the business plan. He sees right through it. He instantly replies like, "Look, I'm never going to invest in a software business, but if you want to meet and get some advice, I'd be happy to grab a coffee." Sam and I meet him. We are all, you know, excited because we're absolutely convinced we're going to dazzle him and change his mind.

Pablo Srugo (00:20:18):
Convince him into changing his entire thesis.
 
Forrest Zeisler (00:20:19):
Yeah. Yeah. Because, you know, you always love your own baby, and we should, you know. Do the shaking of the hands and the small pleasantries. We sit down at the table, and he picks up the piece of paper. He says, if this is your business plan, you're fucked. He then just demolishes us. It was brutal. Like he started off just highlighting that, we did not know how the hell VC worked. You're raising money, you sell part of the business. How hard is that to understand? But he started laying out some numbers. He's like, "Look, you got 500 bucks in your pocket. According to this, you'll spend it. You'll get five new customers. Three months later, you're about to break even. Three months after that, you've made about $500, and you can reinvest it and do it all again. Or you can go sell 10% of your business for $100,000. Go get 1,000 new customers. Three months later, you're about to break even. Three months after that, you've made about $100,000, and you keep 90% of it." Oh, yeah, that second one does sound better. Let's do that. He asked us, what kind of business did we actually think we were going to make? Like, how big is this opportunity? That if this is a small opportunity, not only will we not find anybody who will invest in it, why are we wasting our time? And this is truly a huge opportunity. If there are the millions of businesses that we are claiming, then other people see this opportunity as well. They're going to go hard. They're going to go raise millions of dollars to capture it. And they will steamroll us unless we're like going as hard as they are. He told us to go off and think about what kind of business we want to make. And if we want to have another conversation later, he'd be happy to grab another coffee. I still remember Sam and I stumbling across the street. It felt like we were stumbling across the street. I'm sure we were walking normally. But like just emotionally, it was like, what the hell just happened? And we sat down and we had a good conversation. It's like, you know what? We're going for it. We do see a huge business here. There are the millions of potential customers. And we have talked to so many that we know they all need the software, right? Like this idea of $8,000, MR was long gone at this point. This was the, we're going to go build something that changes the world. Something that millions of businesses can use. That hundreds of millions of homeowners are going to interact with. They'll facilitate trillions of dollars of economic value. Like we're going for it. We put some thoughts together. Enrich our business plan. I think we're up to four pages now. Reach back out and grab another coffee. We sit down, go through our new thinking. And he asks us to, tell us about the market. Tell me about your future customers. We say, they're painters, they're landscapers, they're window washers. You know, there are tons of them. They're everywhere. He's like, "Yeah, but how many specifically? What regions do they operate in? How long have they been in business? How many employees do they have? What's their average revenue? Like, tell me about the market." It's like, oh, we don't know any of that. It's like, go learn about your customers. And if you want to grab a coffee again later, I'd be happy to. So we spend all this time, we're going through census data, Stats Canada, every bit of market research and Gartner reports we can find, and we learn about the customers. We meet up with him again, and he opens the conversation by saying, "If I start giving you $10,000 a month right now, what would you do with it?" It's like, oh, we know this one, marketing. It's like, well, where would you market? AdWords. Okay, what keywords would you buy? Who else is bidding on them? What's the average click-through rate you expect? How much do they cost? What is your marketing plan? Oh, we don't know any of that. We end up going through this cycle four, five, six times. And it's worth remembering that this is a guy who does not know about software. These are just straight-up business questions, right? Not, not software business. Just know about your customers. Have a plan, think deeply about the competition, the market, and where you're going. They were good questions. And at the end of it all, we sit down, we meet him. At this point, we have a 55-page business plan to raise $250,000 of seed investment. He sits there, he asks us every question he can think of. We had good answers for all of them. We were in our pockets, ready to go. He's like, "All right, you're now ready to go talk to software VCs." He basically kicks us out of his office.

Pablo Srugo (00:25:39):
He gave you a lot of time, by the way.

Forrest Zeisler (00:25:40):
He was so generous. And this is why I always try and take every opportunity to pay it forward.

Forrest Zeisler (00:25:46):
If people have questions, if they want to grab a coffee, aspiring entrepreneurs, if a professor comes and asks me to talk to their class about what it's like starting a business, I want to put some of that positive energy and time back into the local community because he was so generous with his time. And I know we wouldn't be here today if it wasn't for him. Yes, we would not have got through the front door of any legitimate software VC from where we had been. We were now ready to go talk to real VCs.

Pablo Srugo (00:26:14):
And talk to me about the business plan, because I mean, business plans are completely out of fashion. Everybody builds a deck, and some people do investment memos or whatever. I actually had built one business plan in my life. And, you know, I must say for me, it was it was questionably helpful because a lot of times it gives like a false sense of certainty, you know, like you answer some questions that are unanswerable. But it sounds like in your case, it helped like, just walk me through maybe pros and cons or something like that.

Forrest Zeisler (00:26:41):
I think plans become worthless the first day you try and start executing against them. But as the saying goes, plans are worthless planning is priceless. That business plan, the value was the act of creation, forcing us to sit down and think through all those steps. Think about all the questions somebody might have. Make sure that we were prepared and making sure that we were aligned. Again, as early founders who just met in a coffee shop, we didn't know what we were getting into. I think it was actually a really valuable exercise to make sure that Sam and I were actually aligned on how we were thinking about this and where we were trying to go. Most startups fail due to founder conflict. Having things written down creates a lot of alignment. So the business plan itself kind of worthless. The way it helped us get aligned and prepare and think through the business at a much deeper level than we had prior was absolutely priceless. I think there are a lot of different ways you can achieve those results. And maybe if you're like a very business-minded individual, you enter the fray already set up to think that way. I know for me, it was a very valuable exercise. Very few things came true from that plan, to be clear.

Pablo Srugo (00:27:55):
Did the $250K come through at least?

Forrest Zeisler (00:27:57):
It did.

Pablo Srugo (00:27:58):
Nice.

Forrest Zeisler (00:27:59):
But that's a whole different story, which I'd be happy to share.

Pablo Srugo (00:28:02):
Go ahead.

Forrest Zeisler (00:28:03):
Well, because now we're ready to start going and raising. But again, Edmonton, Alberta, how the hell do you go and raise money? It's kind of like finding your first customers. You start reaching out, you're cold calling, you're emailing. Every so often, somebody agrees to talk to you, and you get in front of them, and you give your 10-minute pitch. And then would you invest in this business? And then they say no. And then you ask why.

Pablo Srugo (00:28:24):
You're used to that now.

Pablo Srugo (00:28:24):
You're used to that.

Forrest Zeisler (00:28:25):
Yeah. And you take that feedback, and you go and you discuss it, and you either agree with the feedback. In which case you now have to expand the business plan thinking, "How are we going to address that risk? How are we going to mitigate the uncertainty?" Or it's like, I don't believe that's true. Let's go get some facts to be able to explain better next time why they're wrong and why they need to think differently about our business. And you go through this again and again and again. We did it, God, hundreds of times. I don't know the exact number. Felt like it took forever. And we were each just trying to work our different networks, trying to get intros wherever we could. I happened to be living in Vancouver for six months during this period. And I would go to startup events. And I would buy beers for the people I knew who worked at companies that had received venture capital and get intros to the founders of those companies. And then I would go buy beers for the founders in exchange for intros to the VCs. And then I'd go and pitch the VCs. And one really funny thing happened. The one week I went and pitched Boris Wertz from OSN or from Version One Capital. And it turns out Sam had independently, in Edmonton, working his network and connections, got intro to Boris and went, and pitched Boris in the same week. The exact same business. So Sam and I both went in front of him as the two individual founders, both could present the business. We could both talk about the tech. We could both talk about the future and the vision. And even though I think we didn't show the most coordination, we were very aligned, and we could both speak to every part of the business. And I think that was a big part of what helped sell Boris and got him interested that we were both that bought in and that engaged. You know, we were both writing code. We were both pitching to VCs. We could both talk about the future, the market, the competitive landscape, the customers we had, the customers we were going to have. And I think that was a very happy accident for us. But it took a long time before we got that intro with Boris.

Pablo Srugo (00:30:24):
And so he ended up leading that seed round?

Forrest Zeisler (00:30:26):
Yeah. Yeah. It was Boris and Christoph from Point9 Capital. And the two of them together led the seed round. Of course, we get that LOI. We get the letter of intent. And then we go through due diligence. Now you might've caught earlier. I was sharing, the quality of our accounting and bookkeeping, right? Like we just threw money into an account, and then we had a handshake agreement for how much we'd each take out of the account each month. Our bookkeeping was a disaster. We had gotten incorporated. We had created 100 shares. 50 for him. 50 for me. So they started looking at our diligence. It's like, we can't give you the money until all of this is cleaned up. They set us up with an accountant who completely redid our books, figured out all the back tax, figured everything out. They set us up with a lawyer who completely reincorporated us. It took more than six months from them saying they'd give us the money.

Pablo Srugo (00:31:17):
No way.

Forrest Zeisler (00:31:17):
Until we actually got the money in the account.

Pablo Srugo (00:31:20):
Wow. For a seed round?

Forrest Zeisler (00:31:20):
Yeah, for a seed round because we were so un-investable.

Pablo Srugo (00:31:24):
Oh my God.

Forrest Zeisler (00:31:24):
We had the product. We had the passion, but there was a lot of housekeeping that had to be done to get it into a spot where they could even legally give us money. We had to reincorporate. Who were they giving the money to? And we couldn't reincorporate when the taxes were that much of a mess. So we got it all sorted. It got cleaned up. I do think there is a bit of a lesson there, though, that in that position, I would do everything exactly the same way. As a founder, there's not enough time to do everything. And you got to focus on what is your number one job. And it's finding something that people want, that solves the problems, that makes the world a better place, and figuring out how to sell it. Anything like the bookkeeping, the legal. Like, all of that can get cleaned up. All that can get fixed up, and there will be a point where it absolutely has to. And when you're going through that, it's going to be a really painful experience, but it doesn't matter. Your job is to get to a point where you can deal with that problem.

Pablo Srugo (00:32:14):
I'm really worried because, listen. You've been listening for like what, 10, 20, 30 minutes now? Clearly you like it, and the thing is the next episode is way better, and you're gonna miss it, you're gonna miss it because you're not following the show, so take your phone out and hit that follow button. A hundred percent. I remember actually, like I remember as a founder, the list of things to do was just like always infinite, like literally infinite. And I remember I would try and just get everything done and everything done. And there was a point at which I just realized like you're just kind of spinning wheels on a lot of these things. And you almost have to see things as just like ones and zeros. I think it's either a one, has to be done right now. Critically important, or a zero, in which case you could just ignore it altogether.

Forrest Zeisler (00:32:55):
Yeah, it's you're either building shit, selling shit, or it's bullshit.

Pablo Srugo (00:32:59):
How is the business? During this time? You had three customers, but now six months has gone by. Are things starting to click on the business front?

Forrest Zeisler (00:33:09):
I want to say we were up to 10, 12 customers now. So that's 3x growth. That's pretty good. At the same time, it's still nothing. An interesting, or just a fun little tidbit actually, through that fundraising process, we had our three customers. We were in conversations with Boris and Christoph, and we actually lost one of the customers. 33% churn. Yeah. And we were like, we were so panicked. It was like, like it was just gut-wrenching. And we were so worried that it would tank the whole deal. Like we'd never lost a customer before. And when you only have three, that one really matters. And when it's in the middle of a fundraising. It really, really matters.

Pablo Srugo (00:33:54):
And why did they churn?

Forrest Zeisler (00:33:55):
I think they just. They weren't engaging with it. You know, technology adoption, like change management, is hard, right? Failure to launch is still today. Like one of the number one issues that we work on with our customers is how do we as quickly as possible show the value, get them embedded, get them building habits around the technology, right? It's like for the same reason throughout my life, I've joined many gyms and never gone, right? Like, it's tough to build habits. And this person just didn't get a deep enough habit formed around Jobber. And when their business got busy, using us was one of the first things that got dropped off their to-do list. Luckily, it was only one or two weeks where Sam and I were holding our breath, hoping no one noticed. And we got a new sign-up.

Forrest Zeisler (00:34:39):
So we were back at three customers, and we just sort of acted like 

Pablo Srugo (00:34:42):
Nothing's changed.

Forrest Zeisler (00:34:43):
We started with three. We ended with three. Nothing to see here. I'll never forget that experience where I was walking down the street, talking to Sam on the phone, and we realized we just lost a customer for the first time.

Pablo Srugo (00:34:55):
And so now you have the $250K, like, where do you start investing? And when do you start to see, you know, that things are kind of starting to hum? Because, I mean, 10 customers, $30 bucks, like we're talking $300 MRR. Like, there's a long way between then and success sort of thing.

Forrest Zeisler (00:35:13):
I don't think I realized how much of a leap of faith Boris and Christoph were taking on us. I don't know if I would have been brave enough to invest in us had I been in their shoes.

Pablo Srugo (00:35:21):
It's pretty crazy when you think about it. It really is. Like, it was so early.

Forrest Zeisler (00:35:24):
We made our plans that, like, the first thing we needed to do was hire another developer. As we were talking to people, our roadmap was growing. The number of things that we want, to do better was increasing, particularly around mobile. Again, mobile was just taken off. And it was always part of our pitch, always part of our vision. Adoption was very low. Early on, people were telling us we were crazy. You expect every plumber to have a smartphone? Maybe someday the owners would have smartphones. But everybody cleaning a house or pushing a lawnmower, they're not going to have smartphones. Again, it's easy to forget how different things were back then. And of the owners that would use us on mobile, most of them were using us on BlackBerry. iPhone was just becoming a thing. So we used a framework called jQuery. It was a responsive web interface. You'd still get to it through the browser. But mobile was becoming more important, becoming more time-sensitive. We were getting tons of feedback through the usage of our customers. And we had a lot to do there. So we wanted to hire a developer. And the funny thing is, it was the same experience again. Like we were all excited, like, oh, we have $250,000. It feels like all the money in the world. And then you go and try and make your first hire, and you can't hire anyone, right? Because people, I mean, first of all, we still can compete against established employers. We could not pay as much as them, even with this money, like paying engineers at full price, you're not going to hire many engineers, and you won't keep them employed long. And they could see our runway. They could look at our business. It's a huge leap of faith, and finding really qualified developers who are willing to risk their career on our startup in a place like Edmonton, Alberta. Where there is not an ecosystem is a really big challenge. So we would take people out for coffees, and we'd try and pitch them on joining our company. And we'd ask them, would you join Jobber? And they'd say no. And then we'd ask why. And we'd go and refine our pitch and understand what wasn't working. And we kept doing this until we finally got our very first employee, Nathan Youngman. And then we started, investing in our first marketing salesperson, somebody who could, because we were still engaging in all the forums. We were still doing all the trying to get out there and have a presence and act like we were bigger than we were.


Pablo Srugo (00:37:38):
When you were doing any cold outbound, like calling, things like that, it was more kind of top-of-funnel marketing things.

Forrest Zeisler (00:37:43):
At this point, it had started to shift over. Yes. I mean, first of all, we pissed off or convinced most of the people in Edmonton. It's had a very low hit rate. We knew it wouldn't scale long-term, not at $29 bucks a month. Like you can't run a really effective outbound operation. That was one thing we'd learned about the economics of a business. Early on, do things that don't scale. But by now, first employee, I want to say we were 20, 30, maybe 35 customers.

Pablo Srugo (00:38:10):
So, starting to speed up, I mean, the numbers are small MRR wise, but the velocity is definitely there. What was driving that? Was it just like the product was better? The market was changing? Like what started, like what was the undercurrent that was making things flow a little better, get a little easier?

Forrest Zeisler (00:38:24):
All of the above. Yeah, the market was starting to shift to the next generation. It was being handed the keys to the filing cabinet and being told the business is now yours. They're looking at that file cabinet going, isn't there technology that can solve this? Or people were starting to get smartphones. And the product had really matured through all of this. Solved a much richer cross-section and solve things deeply. You know, it's one thing to be able to have an invoice, but at this point you could, at the end of each month, print off a PDF that had like all your invoices, print off a PDF that had all the mailing labels. Again, this is when most things were still done via mail, but sort of those batch processes, and you could support the different sizes of mailing labels. And you could like, again, those aren't new features. It's not feature bloat. It's supporting the businesses in the way they actually need to use them.

Pablo Srugo (00:39:11):
Because you're trying to become like the OS, of the business, like the core of it. So there is a pretty high demand in terms of the number of things you need to enable to just solve that kind of engine problem for a business.

Forrest Zeisler (00:39:23):
When we got started, we sort of had this picture in our head that everybody would be logging into the interface every day. Again, most people, their employees, were not going and doing that. They came to the office and were handed a piece of paper with their jobs for the day. So we had, you can print off your day sheets and hand them out to everyone each day. And everybody would check things off, and then you could put it back in really smoothly into an interface for tracking all their hours. Like we had slowly been bit by bit filling in these feature gaps and the product improvements, the website improvements, continuing to establish a bit of a presence and a name in the forums and in the communities. and then started to do more top-of-funnel marketing. It was all coming together. We got an intern, and we would all take turns writing blog posts in our blog. This is when, you know, SEO was king, and it was just getting known that's the real way to build top-of-funnel. I think content is still very important. The internet's a much noisier place than it was back then. We started sending out newsletters. Like we were trying to do all the things that big companies seem to do. And bit by bit, it was gaining traction. It was continuing to build momentum. Felt good. Felt very, very fragile. Again, we were burning money, and the numbers were still extraordinarily low. We were operating with a tight timeline, but it did feel like there was momentum. And I'll say that Boris and Christoph were extraordinarily valuable. There's actually a piece of advice that I should mention early in the fundraising process, before we'd met these guys, when we were still at the sequential no, after no, after no. Somebody gave us advice: "Never raise money from anyone, who you wouldn't have over to your parents' house for dinner." Really simple advice. It was fantastic. It helped us connect to the fact that these are partners, right? Like it's a marriage. You're not just taking the money and ignoring them. And you want to find somebody who's bringing a lot more than just money to the table. There had actually, in full transparency, there were offers to invest in Jobber before Boris and Kristoff. They weren't the right people for any number of reasons. And Boris and Kristoff, we loved their portfolios. They had companies like Clio, Vertical SaaS for lawyers. They had companies like Zendesk. They were a real shop. We were a real shop. We knew all about Zendesk. It was a real business. And again, it was SaaS. And they were able to sit down with us and start running these monthly board meetings. And we were calling them all the time. Again, most people, they keep their investors at arm's length. Like you got to embrace those investors, like soak up as much knowledge as you can from them. And we were talking to them probably every week. We'd have an official meeting every single month, and we would show them all our KPIs. And they would talk us through it. They'd ask us questions. They'd tell us what things were missing from the sheet, and we'd have to add them for the very next month. And we started with a spreadsheet that had 10 rows, and it slowly grew bit by bit, 20 rows, 50 rows, 100 rows. As we became more nuanced, we started breaking out. the different channels, started looking at the different conversion rates, started understanding our retention more deeply. And it was an educational journey. As the business was getting better, we were getting better too. We were learning what it meant to be running a vertical SaaS business. And that was just a fantastic experience for us. But it was an exercise in imposter syndrome from beginning to end. Because every meeting, you're learning more about what you don't know. And you're constantly feeling like you're unprepared. Every day you're being asked questions you don't know how to answer. It was a really gruelling experience, but we learned a ton through it. And because we kept that open mind and we kept soaking up their knowledge and then taking that knowledge and infusing it into Jobber, Jobber continued to grow.

Pablo Srugo (00:42:51):
And how long did it take to hit like a million ARR?

Forrest Zeisler (00:42:54):
I actually don't remember. I want to say it took about two and a half years to get ours, maybe two years, two and a half years. Somewhere in there to get to our hundredth customer. We were five employees back then. No one was making any money. And we were at about 90 customers, and we had a big whiteboard on the wall and we've like, you know, left slots for one to 10. And every time we made a sale, you know, once or twice a day, we, somebody would run up and write the name of the customer on there. It was our countdown to hit 100 customers. And we actually got to 99, and then we lost one customer. So I had to shift all the numbers around. And then we finally got our hundredth customer. It was Hot Tub Tony. I'll always remember Hot Tub Tony. But that was such an emotional experience, getting that 100th customer. Like I had to sit down and like breathe deep breaths. It felt like, okay, we are a business. I mean, you are a very sustainable business. It might not be very profitable, like there were a lot of problems, but that, a hundred businesses were trusting their businesses to us, their data to us, their daily operations to us. That was an amazing feeling. Right. Like it was a milestone that. Just unbelievable. It was right. Like that was the big moment. Getting our first customer, Graham, was the biggest. Crossing a hundred, crossing a thousand, crossing 10,000.

Pablo Srugo (00:44:15):
How long did that take? Like, from a hundred to like a thousand would have been when? And then the 10,000.

Pablo Srugo (00:44:19):
Let's see. We would have been in our Jasper Avenue office. A thousand would have been somewhere in the, I want to say, 2014 range. I think my memory might be playing tricks with me. It was a long time ago. I remember where I was sitting. I don't remember the dates as clearly.

Forrest Zeisler (00:44:37):
And then 10,000. This would be like 300K-ish MRR. Would be what, like 2016? Yeah, 10,000 customers would have been, yeah, 2016 sounds about right.

Pablo Srugo (00:44:46):
Because it's just interesting. It's such a different ramp than most of the successful businesses that, I mean, top decile is zero to a million in a year. I think there's many successful businesses, big businesses that never even hit that. But you, you know, tend to see like once you hit, I don't know, a million or so, like you have product market fit, then most of these businesses really kind of start to take off at minimum, like doubling every year. But you're, I mean, yours was a slow burn for a long time, but there has to have been an inflection point because now obviously, I don't know if you're close to a hundred million upline, but you guys are so. 

Forrest Zeisler (00:45:21):
Oh yeah, we're well past that now.

Pablo Srugo (00:45:23):
Exactly.

Forrest Zeisler (00:45:24):
So here's the interesting thing. Yeah, I'm probably shifting the dates around a little bit in my memory. I think the big takeaway is that we've, as you can tell from the story, we've never had a pivot. The customers we're serving are the same customers: the painters, the landscapers, the window washers. We're still solving the same problems. We began by talking to businesses, understanding the chaos of their operations and wanting to fill them in. Wanted to use technology to help make these businesses run great. We've never come across some silver bullet feature that changed anything. We've never stumbled across some silver bullet marketing channel that changed everything. If you look at our charts, you won't see a single inflection point, just a slow, steady, exponential curve of every day being 1% better than the day before. But that compounds so that last month we made more new customers than we did in the first seven and a half years of the business put together in one month.

Pablo Srugo (00:46:21):
Right, right, right, right.

Forrest Zeisler (00:46:22):
Like, so that exponential curve of just keep grinding away, get a little better, a little better, a little better. Like, you can't underestimate the power of those cumulative changes.

Pablo Srugo (00:46:33):
But you were still, I mean, there was, there must have been a point where you were, what, doubling every year? Like, was that kind of your growth rate?

Forrest Zeisler (00:46:38):
I mean, we were tripling or quadrupling at this point. Yeah. But it didn't feel like an inflection.

Pablo Srugo (00:46:44):
Sure. Yeah. It was just kind of the same.

Forrest Zeisler (00:46:46):
Again, we serve, with, you know, that, you know, six months or one year to three customers, you know, then you get to, you know, six months later, you're up to 10, 12, like you three X, we probably like end up 10 X'ing or 20 X'ing in that first year. Then, you know, you work your way up to a hundred, you work your way up to a thousand. Yeah. You work your way up to 10,000. You just keep compounding. But again, when you stand back and look at the charts, you can't point to where it starts taking off.

Pablo Srugo (00:47:14):
Incredible.

Forrest Zeisler (00:47:15):
That's what I love about SMB Vertical SaaS. It feels like the most honest business there is. There's almost never a silver bullet. You're selling the software to the people who are using the software, right? You are competing against their personal credit cards, right? Like it's their money. And they're sitting there buying groceries, buying a new barbecue, and buying the software at the same time. So the value has to be really, really evident. There's nowhere to hide. And they decide every single month if you've earned the right to their money for one more month. You're working in large numbers. You don't go make a big enterprise deal. It's tens of thousands of people every month looking and voting on if they think they're going to place their trust in you for one more month.

Pablo Srugo (00:48:04):
So let's stop it there. Maybe end on the questions that we always end on. The first one is, I'm curious if you described it, but when was the first time for you that you felt like you were a true product market fit?

Forrest Zeisler (00:48:16):
Well, as I mentioned through the stories, I had a bunch of times where I had this false impression of product market fit because I didn't know what it was. Like our very first customer, I thought we had product market fit. Our 100th customer, I thought we had product market fit. When we crossed 1,000, that's probably when I actually thought. Like 100 is like we have a business. 1,000 is, we have product market fit. 10,000 is we have a path to building something large and amazing.

Pablo Srugo (00:48:40):
How many customers do you have today?

Forrest Zeisler (00:48:41):
We're being used by, about. Trying to remember the exact number, about 290,000 service professionals.

Pablo Srugo (00:48:47):
Wow.

Forrest Zeisler (00:48:47):
Yeah. We're about just under 1,000 employees. We've raised $180 million in venture capital, USD. And we're continuing to just compound that. How do we get a little bit better every single day?

Pablo Srugo (00:49:01):
And as you said, well beyond $100 million top line, which is probably the most, for me at least, always the revenue metric. And crossing $100 million is just a huge, huge milestone. And then let me ask this. Was there ever a time, I'm sure there was, maybe you can describe one, like where you thought this just wasn't going to work and that this might just completely fall apart and fail completely?

Forrest Zeisler (00:49:20):
Many times, probably one of the most impactful was the story I shared where we lost customer number three. When you spend so long to get a customer and then you lose that customer, you start questioning everything. And I was so close to throwing in the towel. Going and raising money from parents to pay rent, you're questioning everything and thinking, like, am I going to be here in six months having to go do this again, go ask my parents for more money? Like, when is the time to give up and go act like a grown-up, get a job, put on a suit and tie? We're lucky we both had very supportive families. Very encouraging. I think there was a bit of a naivety, ignorance is bliss, that Sam and I had as well. We always felt like we were one feature away, one change, one marketing channel. Now I know, looking back, we never hit a silver bullet. As a founder, you keep expecting there to be a silver bullet, right? You know, you're trying all these new things every day. It's like you just need one of them to really hit wood. Everything will change in the business, and you'll hit your inflection point. You'll hit your viral moment. And that false sense of confidence that we were just one change away from success, I think, kept us going through those tough times.

Pablo Srugo (00:50:27):
Well, let me ask you this last question. I always ask about a piece of advice, but I'll make it more specific. One of the things that I find is the hardest, for early-stage founders especially, is when do you keep going? When do you kind of jump ship or completely do like a hard pivot? You went through a very long, slow burn, right? Many, many no's for a long time. And I think I have to imagine you spoke to a lot of people, investors and others who maybe looked at your numbers and said, Listen, buddy, there's nothing here. You know, try something. How, like, what's your advice to founders in that boat? Like, how should they think about that decision of keep going or kind of jump ship?

Forrest Zeisler (00:51:11):
Well, I do want to preface really the advice I should have given right out of the gate, which is there's a huge survivorship bias in anything I'm seeing, anything you hear from any successful founders. For all I know, there were 99 other founders that did everything I did who are not here today. And I'm always nervous that I'm the guy who won the lottery, and I'm now writing books about how to go win lotteries. Take everything you hear with a big grain of salt. But for us, we had a vision to go solve a set of problems for an underserved market. And no matter how tough things got, that never changed. There were still 6.2 million small home service businesses, 97% of them were under 25 employees. They all had chaotic internal operations, and no one had built a good solution for them. And those were the facts. And if, right, like, no matter how little money we have in our bank accounts, those facts aren't changing. We built careers around going around and helping small businesses solve their problems. And we just saw that problem, and we knew we could solve it. And we just knew it in our hearts. Like we knew it in our souls, and we just weren't willing to give up because it felt so obvious, right? Like the best ideas usually are. I think that just gave us the drive to keep going through the tough times.

Pablo Srugo (00:52:36):
Awesome. Well, Forrest, thanks so much for sharing your story and Jobber's story. It was amazing. And I'm sure founders have learned a lot.

Forrest Zeisler (00:52:44):
Well, I hope I can help. And I'm glad I had a chance to pay for just a little bit of what that VC at the beginning of my story was able to give to us. Thanks for having me.

Pablo Srugo (00:52:53):
Thank you. 85% of people who listen to the show just started listening to it this year. You're probably one of those people. In fact, the odds are 85%. Guess what? You need to go back because there are over 100 other episodes that you need to check out that are just as good, if not better, than this one. Don't miss out.