Tyler King (Edition # 7)

Tyler King (CEO and Co-founder of Less Annoying CRM)

(Tyler King, CEO and Co-Founder at Less Annoying CRM)


We are excited about today’s Edition of The Takeoff. Today’s interview is with Tyler King, CEO and co-founder of Less Annoying CRM. The interview took place via a phone call between Tyler and Roshan Chandna (Co-founder at The Takeoff) in mid-March.

Currently based in St. Louis, MO, Less Annoying CRM is a simple CRM built just for small businesses.

We hope you enjoy today’s Edition.



Roshan: To start, can you give a quick overview of your background and education?

Tyler: Absolutely. My name is Tyler King, and I grew up in St. Louis and went to college at Washington University in St. Louis. I didn't know what to major in and hated computers at the time I entered WashU, but I ended up somehow being a computer science major. So yeah, my background is just accidentally falling into computer science. I graduated in 2007, right before The Great Recession, and made my career from there.

Roshan: What exactly is Less Annoying CRM?

Tyler: For people who don't know what a CRM is, CRM stands for Customer Relationship Management. Everyone has an app on their phone, like an address book or a contacts app, that has all of the people you know in it. A CRM is basically that but for businesses. So, in addition to just keeping track of contact info, it lets you share contacts with other people at your company. 

CRMs can also keep track of your leads, like where everybody is in the lead process, and basic financial reporting, those types of things. So, that's what a CRM is. 

There are a lot of CRMs out there. The thing is that most CRMs were designed to be used by really, really big companies. For example, Salesforce is the biggest CRM, and they're primarily used by huge Fortune 500 companies. Less Annoying CRM is basically solving the same problem that all the other CRMs are solving, but it is doing it in a really simple, straightforward way. If you think about a small business, a company with one to twenty people that doesn’t have an IT team, they don't have a lot of sophisticated needs, they just want something straightforward and easy to use to keep track of all their customer information. That's what Less Annoying CRM is for.

Roshan: Awesome! Great explanation of CRMs, really helpful. How did you come about starting Less Annoying CRM?

Tyler: It was kind of an accident. I think a lot of entrepreneurs have this story of, “I was selling lemonade as a kid and I've been an entrepreneur my whole life.” That's not true for me at all. I wasn't interested in computer science in college, and I wasn’t interested in entrepreneurship after I graduated. What happened is I started working at a tech startup after I graduated, and when the 2008 recession hit, almost everyone got laid off. I was one of five people out of thirty who kept their jobs, and the reason is because I was one of the cheapest people and they kept the five cheapest employees because we were the only ones they could afford to pay.

I showed up to work the next day and didn't have a boss – the CEO literally laid himself off – so me and one other person just took the reins and said, “I guess we're in charge of things now,” because no one told us “no.” That’s how I personally got into entrepreneurship, just everyone else got fired, and someone had to do it. 

After a year of doing that, I was like, “this is great, I love the challenge, and every day you're doing something different and learning something new.” But I still didn't actually have any official authority at that company, so I was like, “if I'm playing the role of the leader of a company, I might as well actually own the company.”

In 2009, I quit that other job, and my brother and I decided to start our own thing. We actually made that decision before deciding that it would be Less Annoying CRM. We just said, “we're going to start something. What's it going to be?” and then went through a process of saying, “well, what problems do we know exist out there that need to be solved?”

At my previous startup, I had seen that CRM for small businesses was something that we were tangentially related to and I could tell there wasn't a good solution out there, so that's why we picked this as the business to start.

Roshan: What made you and your brother decide that you needed to go into business together?

Tyler: We had worked on projects with each other before, and I think a really important milestone for a new startup is: who do you start it with? It's really hard to start a company by yourself. It's not impossible, but it's so much easier if you have a good co-founder or two, but it's hard. The analogy that's often made is that it's like getting married. You don't want to go on one date with someone and then propose. Rather, it's best if you have a good relationship and you've worked together. That doesn't mean they have to be your family, but ideally, if you're starting a company with someone, you know them really well.

Bracken (my brother) and I had worked on other projects before, just hobby projects as brothers. We have really good complementing skillsets: he's really good at server infrastructure, really backend type of coding, and I'm more the frontend design and user interface type stuff. Between the two of us, we’re pretty decent at making products. I think he’s a little less entrepreneurial than I am. He’s not quite as much of a risk-taker.

I said if he’s ever interested, I'll quit whatever I'm doing and just do it. I think there's a lot of luck involved in starting a company, but a lot of what looks like luck is actually just when opportunity slaps you in the face, you have to take it. One day, he just approached me and was like, “you know, I'm kind of interested in this idea.” What we ended up doing was a different idea, but he was interested in it. I said, “well, that's it. This guy's really talented. I know I like working with him, I'm just going to dive in headfirst.”

Roshan: When conflict arises between the two of you, how do you generally go about resolving it? What’s that like?

Tyler: I'm lucky that we don't have a ton of conflict. It helps that neither of us are particularly motivated by money nor status. I think a lot of co-founder conflict comes down to those two things: who makes the most money and who's perceived as being in charge. Neither of us are particularly motivated by that, and just from day one, he was comfortable with me being the CEO. I would say the business is more my life, whereas he has a family and all that stuff. He likes the business, but we haven't really butted heads on that too much. I wouldn't say we have a ton of conflict.

I will say if there is conflict, what we try to do is not compromise.

Compromise basically means one person thinks one thing and the other person thinks the other thing, find something in the middle so that both people are not unhappy. The problem is, when two people disagree, one of them is probably wrong. If you compromise, you're half doing the wrong thing. What we try to do anytime we disagree on something is say, “listen, we both respect each other. We both have similar views of the world and opinions. If we disagree on this thing, one of us is probably wrong, so we just need to talk about this until we admit who that is.” That doesn't work if there's a lot of ego and people are defensive and afraid to admit they're wrong, but if you have a really strong relationship with someone, most of the time you can talk through it and it's not necessarily the case that you go with one person versus the other. Normally what comes out of that kind of discussion is there's a third option that's better than what either of the two of us were saying. It's not a compromise, it's like a whole different idea. That's the most common outcome whenever we disagree and have to resolve it.

Roshan: What has it been like growing Less Annoying CRM? How has scaling the business been for you? What have been some of the challenges you have faced while scaling the business?

Tyler: We are both engineers. Every business has a lot of different challenges and based on what you're good at and what your co-founder is good at, some things will come easy, and some things will be harder. Neither of us are particularly good at the growth side of things, so that's something that's harder for us.

I'd say we still haven't really figured out a great repeatable marketing channel or anything like that. We have a little over two and a half million dollars in revenue, so we have grown, but our basic model starts with struggling to get a customer, and when I say struggle, I mean maybe we're paying a lot of money for ads, or, there's all kinds of different ways to market a software business, and we do them, just not super effectively. We don't have any kind of exponential viral growth or anything like that. Our whole approach to growth is once you have someone as a customer, just blow them away. Give them the best product possible at a low price, and in particular we have really, really good customer service. Our whole growth model is really around making our current customers happy, and then they refer people, so word of mouth growth.

The downside to word of mouth growth is that you can't control it. If we say, “we're ready to ramp things up, we want to double our growth,” there's just nothing we can do. The good part about word of mouth growth is that it's free, and it's really sustainable. So, right now, it's looking like there is maybe another recession coming. I feel a lot more comfortable relying on happy customers to fuel our business for the next few years than I would if we relied on some kind of trendy marketing campaign that could easily stop working overnight.

Roshan: Related to the growth question, but why did the two of you pick San Francisco to start a business, and what made you move to St. Louis?

Tyler: San Francisco was just where I wanted to live. My brother was actually in Boston, so we started the company remotely. I was living in Utah working at that other startup I was talking about and then I moved to San Francisco. It really had nothing to do with, “was that the right place to run a business?” It was just where I personally wanted to live.

The reason we left is that San Francisco, or the Bay Area in general, is the world capital of startups. That comes with a lot of advantages: there's a huge ecosystem, lots of investors, lots of mentors, lots of employees to hire – but there's really one model in the Bay Area and that is to raise money from venture capitalists and try to blitz scale, which is growing as fast as you possibly can.

We're a bootstrapped company. We didn't raise any money for investors. I personally am very against raising money from venture capital. I think that it's problematic in a number of ways. When we got to the point where it was time to start hiring employees, it was really hard to be in San Francisco competing with all these companies that raised $100 million from investors when we had raised none. Everybody in San Francisco wants to go work at the funded companies. 

We considered a lot of different cities: Portland, Denver, Pittsburgh, Baltimore, etc. We ended up picking St. Louis partially because I'm from here and like it, but we also realized it's a much better place specifically for a bootstrapped company. It's a place where employees value stability more than they value rocketship success. People value customer service a lot more. Whereas in the Bay Area, everyone wants to automate everything away.

We basically just looked at our culture as a company and what our goals are, compared them to what the culture of different cities are, and St. Louis was a good fit. I'd encourage anyone who's trying to start a business to think that way. Not just to say, “I have to be like every single startup in the world,” but to say, “what's going to be unique about what we do?” That can help inform a lot of your decisions, including what is the best city to be in.

Roshan: Did you feel there was a shift in company culture when you moved from San Francisco to St. Louis?

Tyler: Definitely. Part of the reason for that is that prior to moving to St. Louis, we were hiring people I already knew. We had six employees when we moved to St. Louis, but they were all kind of friends of mine who were already more experienced, and they weren't exactly co-founders but more of that type of relationship.

When we moved to St. Louis, the big reason we wanted to be here is that it's a great place to hire entry-level talent. There aren't a lot of already successful tech companies in St. Louis the way there are in San Francisco, so there are fewer experienced people to hire, but there's just an absurd number of really smart, talented, hungry, more entry-level young people to hire. That's who we started hiring when we came here, and that's the big thing that shifted the culture, as it shifted away from people who already had experience at other companies and knew what they were doing, to building our own culture for the first time ever, which was just a mix of all the people that we hired from the local universities.

Roshan: You mentioned that there are a lot of resources, such as mentors, in the Bay Area. Related to that, has anyone been a mentor to you while growing Less Annoying CRM? Is there someone you can consistently call when you need help?

Tyler: One of the best ways to get mentors is to raise money from investors and then they become your mentors. Since we didn't do that, I didn't really have that network. What I've found really, really helpful is to try and connect with other founders, even if they're not necessarily ahead of you. When you think of a mentor, you think of someone who knows all the answers to your questions. You don't necessarily need that. I think it's good enough to just have someone who can commiserate with you.

The work of a founder is a bit lonely because even if you work with a lot of other people at your company, the role that you have is different from what everyone else at the company is doing. I've found that in St. Louis it is really easy to connect with people since it's sort of a smaller scene. There are tons of other founders that are really easy to get access to.

So, I can't say any one specific person, but definitely being connected to other founders and not employees of yours, not executives at big companies, but people starting other startups that are of a similar size to you, has been really helpful for me.

Roshan: You said that you are now hiring more entry-level, younger people for roles in St. Louis, what do you look for in the people that you're hiring?

Tyler: It depends on the role. There is some stuff that no matter what the role is, you've got to have it. One is just attitude. We don't really have a good management structure set up because we're only 18 people right now, so we don't want to be looking over your shoulder micromanaging. We really look for people who are just going to come in and be intrinsically motivated to do their job well. What that really means for me is someone who just takes pride in their work and wants to do a good job, almost like an artisan.

Another more specific skill is communication, and in particular written communication. We're a tech company, so we employ programmers a lot, and then also people dealing with customers. It's obvious the people dealing with customers need to be strong communicators, but we way over-emphasize communication relative to other tech companies among our programmers. If I could go back and do it all again, I’d do it the exact same way. Someone who can't write well, it doesn't matter what their job is, is really hard to collaborate with. In startups, things are changing constantly, so there is a lot of room for confusion and chaos. Being able to communicate, to me [as CEO], is the number one skill that everybody needs to have.

Roshan: In addition to promoting company communication, if you were to start another company, is there any other advice that you'd give yourself?

Tyler: Let me reframe what you asked a little bit, which is to say, “what's the biggest mistake I made?” 

It was transitioning from being a founder who is doing all the work to being the leader of a team, where more of the work is being done by other people. If you're going to hire people, this is a transition that every entrepreneur has to make. I was a really natural fit for being the main contributor, like, “I'm building the product, I'm doing the customer service, I'm doing all this stuff.” When we transitioned to, “now we have employees and they need to be contributing more than I am,” I jumped too quickly into the mode of thinking, “I'm a big picture person now. I'm the CEO, and I just need to put people in a position to succeed and let them go and they'll go do it.” There's a middle phase where you're still doing a lot of the stuff but you're just not doing all of it. At an 18-person company, what we are right now, it's not big enough for there to be a full-time CEO. I need to be more in the trenches than the CEO of a 10,000-person company, and I just tried to sort of skip that phase.

There are three phases: one where you're an individual, one where you're a small team, and one where you're a big team. I tried to skip from individual to big team. It really did not work well, and some of the hardest times we had as a company were because of that. So, if I could give myself advice, it would be to just embrace the size that you are; every company doesn't have to be huge, every company doesn't have to scale super fast. I would have enjoyed the journey more, and we would have been more successful if I had just leaned into that.

Roshan: This is a question I've taken pretty much straight from Harry Stebbings over at The 20 Minute VC because he was a big influence for myself and the rest of us starting The Takeoff – do you have any favorite books, movies, TV series, video games or anything of that nature that you’d recommend to our audience?

Tyler: My favorite book related to business and stuff is The Mom Test. It's really short. I don't read long-form stuff very well. I don't have that much patience, but for someone who's not super comfortable talking to customers, especially in the early days when you're trying to validate an idea and get your first customers, The Mom Test explains, in a very concise way, how to have those conversations. In particular, what I love about it and the reason it's called “the mom test,” is the premise, “if you ask your mom if your startup idea is good, she'll always say yes because she loves you. How do you get people who love you to give you honest answers?” Then you use those tricks with customers.

Customers try to lie to you all the time. You're going to pitch them, and they’ll say, “oh, yeah, that's really interesting, maybe let's touch base in six months.” That's really them saying, “No!”. The Mom Test gives you the tricks to have a conversation with somebody where you get the truth from them, and that's super important for moving fast and validating ideas at a startup.

Roshan: A lot of our audience members are college students or recent graduates interested in careers in technology and startups. If you were graduating from college tomorrow, what do you think you would do professionally, and what advice do you have for people in our audience who are about to graduate college?

Tyler: Let me give two answers to that. The general answer is just don't get in your own head and make up excuses to not do something. I know so many people who have wanted to start a business, but they're just waiting for the right time. The reality is, the first thing you do will probably fail, and the second thing you do will probably fail, so rather than obsessing over getting it right, the best thing you can do is just do it. Start something. Even if it fails, you'll have learned more than you would have by over-preparing and saying, “the timing isn't right, I don't know who my co-founder is going to be, whatever.” Just get started. Do it! You'll learn super fast that way and be in a great position.

For the more specific advice I would give, this may sound stupid if you listen to this a month from now, but it really seems like there is going to be an economic crisis happening (Keep in mind this conversation is from mid-March). The world is changing really fast right now with COVID-19, and if that happens, people who are graduating right now are going to be entering an absolutely terrible job market, which sucks. It might be scary, but I'll just say I was kind of in the same position.

I graduated a year before The Great Recession, but my early “just out of college” years were in the worst economy that the world has seen since The Great Depression. It's hard, but what I would encourage everyone to understand is that it' is like a forest fire. Everything burns down, there is a lot of death and destruction, and it sucks. But, right after that is the highest period of growth that you ever have and that the economy is ever going to have.

People who are in college right now are going to think this is really bad timing, but if you're an entrepreneur and you're thinking about starting something, there is going to be no better time than right after or during an economic crisis to start something and to build something new, because everything's destroyed and you're starting from square one, just like everybody else.

Roshan: Great advice! Thank you so much for being on The Takeoff. I'm sure everyone reading has learned a lot.

Tyler: Thanks for having me. It's my pleasure!


** Please note that our interviews may be edited for length, content, and clarity **


Moderator: Roshan Chandna (Co-founder at The Takeoff. Sophomore at Washington University in St. Louis. Incoming Summer Analyst at Octahedron Capital)


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