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Growing My Business by Being Patient Where Others Might Rush

Hello! What's your background, and what are you working on?

Hi! I'm Tyler, and I'm the CEO/co-founder of Less Annoying CRM (or LACRM for short). My background is in software development and product design, but since starting LACRM, I find myself doing a little bit of everything.

LACRM is a bootstrapped SaaS company based in St. Louis, Missouri. We make a simple customer relationship manager specifically for small businesses. As you may know, there are a gazillion CRM companies out there so the competition is fierce, but it's also a huge market so everyone ends up finding their own niche. In our case, two things that set us apart:

First, our design focuses on the end user of our product (sales reps, support reps, etc.) rather than managers/executives. We focus on making a product people will want to use even if it comes at the expense of automation and reporting which is what the higher-ups normally want. Generally, if a company is big enough that the person in charge of purchasing CRM software isn't going to actually use it themselves, we'll lose the sale.

Second, we invest heavily in customer support. That means customers who are older, less tech savvy, or who just don't want to figure things out for themselves prefer working with us.

My brother Bracken and I started LACRM in 2009. Our team is now 11 people (with two more starting later this year) and we're making about $120,000 in monthly recurring revenue from 12,000 paying users. (Our product costs $10/user/month, so the math is pretty easy.)

What's the story behind how you started working on Less Annoying CRM?

I ended up here almost entirely by mistake. I majored in computer science in college, and during my final year a friend from high school convinced me to join a VC-backed startup he was working at in Utah. I had absolutely zero interest in entrepreneurship, but it seemed like a promising company that was about to take off, so I took the risk and joined. About a year later, funding dried up and almost everyone at the company got laid off (it was 2008, so this was happening all over the place). I was at the very bottom of the org chart, so I was one of the few people they could afford to keep.

Over the next year, I got an insane crash course in entrepreneurship since literally everyone above me at the company had been laid off, including the CEO. Along with a couple other low-level employees who survived the layoffs, I basically got to do whatever I wanted with the company. We didn't know what to do, so we just experimented with the business model until eventually we were able to get the company to profitability. One day I realized that I was playing the role of an entrepreneur, and I loved it. I figured that I'd be better off starting my own company.

I'd worked on a bunch of side projects with my brother, Bracken, and I knew we worked well together. My brother is the most talented person I've ever known. One day, he reached out to me with an idea for making an app to let people make pretend trades on the stock market and track their performance. I didn't care about the idea, the timing, or anything else. We immediately agreed to start the company. I quit my job shortly after that.

It didn't take long to realize the stock-trading app was a bad idea. It would be really hard to monetize and might have some regulatory mess we didn't want to deal with. So then we came up with an idea for an app to automatically modernize small business websites. We decided that wasn't good either. We ended up brainstorming and cycling through a lot of different ideas before settling on one we both liked.

At my previous startup, I'd built a little internal CRM to help our resellers track the customers they were referring to us. Those resellers were mostly independent insurance agents, and when they saw the CRM I'd built, they flipped. Many of them had never heard of a CRM before and loved how much it helped them. I had experience setting up Salesforce for that startup and knew how complicated it could be. Those experiences led to an idea Bracken and I could both agree on: Less Annoying CRM.

LACRM Workspace Screenshot

What did it take to build and launch the initial product?

Bracken and I combined had all the skills we needed to build the product. He does DevOps and back-end development, and I do design and full-stack development.

I had a pretty good idea of what people wanted from my experience working with insurance agents at my previous company, which allowed us to cut some corners in terms of customer research. We just threw together some rough mockups and then put our heads down and coded until the MVP was done. It took about three months for us to put together a basic PHP/MySQL/jQuery web app that we thought was good enough that someone would want to pay for it. Of course we would eventually learn about all the things we got wrong, but we got enough stuff right that we were able to start selling the initial product.

Given our backgrounds, product was the easy part. The hard part was everything else. We basically had no idea how we would get customers. We didn't know what, if any, legal and accounting requirements we'd need to take care of. We didn't even know where the company would be based at first. (I ended up moving to San Francisco while Bracken was in Boston, and we just worked remotely.)

If I've learned anything over the last 7.5 years, it's that nothing is ever easy, and magic bullets don't exist.

Probably the biggest thing we had to figure out was money. At my previous startup I saw the dark side of Venture Capital, so I knew that bootstrapping was the only option, but we still had to pay the bills. This meant that Bracken and I each worked other jobs on side so that we could pay our own living expenses plus the minimal costs of running LACRM. This continued for about 3.5 years before we could support ourselves with revenue from LACRM. He was a full-time PhD student for the first couple of years, and then joined a biotech startup in Boston. I was lucky enough to get a gig from my last company consulting/contracting for ~20 hours per week, and I also started a food blog with my mom on the side to supplement my income while we waited for LACRM to take off.

I'm not going to lie, working other jobs while trying to start LACRM was tough. I just wanted to put every ounce of energy I had into LACRM, but I couldn't afford to. This meant the initial launch and the first few years of the business were slower than they could have been. But in my opinion, the tradeoff was well worth it.

What strategies have you used to find customers for Less Annoying CRM?

There's a lot to cover here. I should probably start by saying that we didn't have a "launch" per se for Less Annoying CRM. There was no blog post or Hacker News submission. We didn't have a list of people who wanted to be emailed. I don't even think I posted about it on my personal social networking profiles.

Throughout the entire history of the company, we've never had a single individual thing that resulted in a meaningful surge of new customers all at once. (And we've been at the top of HN a couple of times, it just didn't actually do anything for us.) It's been an incredibly slow boil for the past seven-and-a-half years, and I expect that to continue indefinitely.

When we started, we didn't have any kind of real marketing strategy, but we figured we could get some eyeballs on the site with Adwords. We realized that we were still learning and that the ROI would probably be terrible, but we didn't have any better ideas. And even though we were right about the ROI, we actually were able to afford a small trickle of visitors who eventually turned into paying subscribers. We were at 6 paying users after 6 months, 47 after a year, and 200 after a year and a half. We suck at marketing, so this was a really slow process, but eventually we built up enough momentum that it seemed like this business might actually work out.

Month Revenue
Jan 0
Apr 4
Jul 9
Oct 19
Jan 47
Apr 115
Jul 200
Oct 376
Jan 584
Apr 745
Jul 1048
Oct 1243
Jan 1476
Apr 2017
Jul 2535
Oct 2933
Jan 3391
Apr 3941
Jul 4489
Oct 5162
Jan 5714
Apr 6480
Jul 6996
Oct 7394
Jan 7923
Apr 9011
Jul 9835
Oct 10793
Jan 11297

This is what slow but steady growth looks like.

There are two key things I learned in this process that no one wants to hear:

First, customer acquisition channels come and go. Adwords was our only source of traffic for a while, but it just got more and more expensive until we had to stop using it entirely. Around that time, the Chrome Web Store picked up. That was awesome because we got a ton of leads and they were 100% free, but Google neglected that project and it eventually became irrelevant. This is an emotional rollercoaster if you're not ready for it.

Now I realize that it's important to have multiple different channels running in parallel, and you always need to be looking for the next thing because your current channels won't work forever. We currently get customers from our blog, our email newsletter, listing ourselves in app directories, using lead generation companies (not spam-type stuff, more like matchmakers between us and interested buyers) and many other things. I sleep better at night knowing that we aren't relying on any single channel.

Second, nothing scales. Like, nothing. The dream is to find some marketing channel where you can buy a user at some acceptable amount. (For us, that's $100-$150 per paying user we get.) Then you have a machine where you can just pour money in the top, wait a few months, and even more money comes out of the bottom. The problem is that with every single channel I've ever tried, even if it works at low volume, the ROI gets worse and worse as you try to ramp it up. It's yet another reason to have multiple channels running in parallel rather than one monolith.

But forget everything I said above. By far the most important factors in our growth are low churn and high word-of-mouth. I really don't know how to market and no one should take marketing advice from me, but once we get a customer, we've had great success in keeping them and getting them to tell their friends. Almost all of our growth is organic. There are downsides to this: it takes a long time, there's no way to step on the gas, etc. But it's way less fragile and more sustainable than any marketing channel I've ever tried.

When we started, we thought the key to making customers happy was building a great product. That's obviously true to an extent, but every other software company is trying to do that too. But there's something that very few other software companies are doing that is even more impactful than having a great product: customer service.

We win so many sales just because we're willing to pick up the phone.

We discovered this completely by mistake, but the benefit we've received by offering fast phone and email support for free is immeasurable. I'd even go so far as to say that the most important thing I do right now as CEO to help grow the business is recruit the best support people possible. The rest takes care of itself.

What's the story behind your business model and revenue?

This section is going to be really disappointing, because there's just nothing clever or interesting going on with our business model. We charge $10 per user per month. We have literally never charged anything other than that to anyone. Some customers choose to pre-pay, but it still comes out to the same price in the end.

How'd we land on $10? It just seemed like a nice round number, and we thought it would be enough for us to be profitable.

This is where almost every SaaS thought leader will tell me I'm an idiot. I always read "just charge more" as the default advice from pretty much everyone who's ever made a dollar on the internet. I dunno, that just doesn't really motivate me.

Figure out what you want out of this, and use that lens anytime you take advice from anyone.

Thinking about money and profitability and your business model is super important if you aren't profitable. But as soon as your business becomes profitable, then you have the freedom to decide for yourself what you care about. If "maximizing shareholder value" is your idea of an inspiring mission, then go for it. But that's not something I care much about. I know we could make more money if we raised prices, had extra tiers, took credit card info up front, required annual contracts, etc., but I'm making plenty of money right now, so I just don't see any reason to stress out trying to solve those problems that don't interest me.

To me, this is one of the biggest benefits of bootstrapping. There's nothing stopping bootstrappers from trying to make as much money as possible, but they also have the freedom to optimize for other goals instead. The second you raise money from investors, you really don't have a choice.

Ok, I'll get off my soapbox now and end with a couple of random tidbits about the revenue side of the business:

  • We didn't have a working billing system until a few months after we got our first real users. We just made up reasons to extend their free trials (like, "thanks for finding that bug, here's two free months") until we had time to finish the billing system.
  • We use Stripe for our billing. I really love them, although I personally am of the opinion that it's best not to outsource recurring revenue logic. We handle all the logic, emails, etc. in our code and Stripe is just a dumb API for charging their card when we tell them to.
  • Because we're bootstrapped and don't have any plans on exiting, giving out equity to employees would be an empty gesture. Instead, we came up with a unique profit sharing plan that pretty closely mimics the behavior and incentives of equity.

What are your goals for the future, and how do you plan to accomplish them?

Short term, our goals are mostly focused on building out the team, and increasing our product development capabilities. The company has gotten too big for Bracken and I to be the primary coders now. We're learning how to hire and develop technical talent, so we can hopefully polish up our product and put out some key features our users have been waiting on: a new calendar, vastly improved custom fields, a better mobile experience, etc. In the last 1.5 years we've gone from two developers to four (with another starting this summer) and switched to a new React-based front-end framework, so I think we're in a great position to really ramp up product development.

Longer term, it's harder to say. There's definitely a chance that we'll just keep growing gradually (or even plateau or start shrinking) and just kind of keep doing what we've been doing. But I'm hoping that we can go after some grander ambitions.

This is probably a bit of a pipe dream because if I've learned anything over the last 7.5 years, it's that nothing is ever easy, and magic bullets don't exist. But I'm not letting that stop me from dreaming big. The real vision for the company is to eventually put out a suite of different products that can handle virtually all of the technological needs for small businesses. We have tons of product ideas (including mockups, marketing ideas, etc.) but we don't yet have the resources to really swing for the fences.

What are the biggest challenges you've faced and obstacles you've overcome? If you had to start over, what would you do differently?

I've made so many mistakes over the years, but one nice thing about slow, steady growth is that I've normally been able to identify and correct my mistakes before they became huge issues. There have been multiple times where I made a major decision (completely re-writing the code base in a new language I'd never used before, pivoting the product, etc.) and started down that path, only to realize my mistake a month later and roll it back. If we were growing at unicorn startup speeds, we would have been in too deep before realizing the mistake, and we probably would have failed by now.

Having said that, there was one challenge we faced that I didn't handle well and I'd love to be able to do over. When we started, my brother and I weren't really thinking about hiring people, getting an office, or doing any other "real company" things. We just wanted to make a great product that our customers loved. When it became obvious that we were on to something and that we'd need to start building a team and acting like a real company, the transition was really hard.

LACRM Team

The Less Annoying CRM team.

The approach that I took was to try to hire really talented people to own major parts of the business, and just assume that they'd be able to do better than I ever could. I actually successfully recruited a few great people who were clearly better than me and smarter than me (at least within their areas of expertise) and I just kind of thought I could stop worrying about what they were now overseeing. We had great leaders for the tech stuff, marketing, sales, and customer service. My job would just be to coordinate all of them. Simple, right?

Anyone who's done this before is probably shaking their head right now. I was incredibly naive and unprepared. And since this decision involved hiring people, it wasn't as simple as "rolling it back". For two years we tried to make it work. During that time, the company experienced major successes on the customer service side, but tech and customer acquisition struggled. Things just weren't working. Whatever mojo we had before this transition had been completely lost. Eventually, two of the four leaders we hired left the company which was hard to handle, but definitely for the best. I learned a ton from that experience and put together the following list of rules for growing going forward:

  • Smart people in a room together don't automatically produce results. As the CEO, I need to lead and enable them, no matter how capable they are.
  • Culture and mission matter. It doesn't matter how talented an employee is if they're trying to accomplish things that are antithetical to the mission of the company.
  • No one should be siloed. Particularly at a small company, everyone needs to know what everyone else is working on. Collaboration is key.
  • Build off what we have. Whether it be marketing, customer service, or product, all improvement should be iterative. Trying to start some projects from scratch killed our momentum.
  • Grooming entry-level employees is preferable when possible. This might not be the best advice for every company, but we've found that getting an entry-level hire to fit into the current system and improve it is much easier than getting an experienced person to do that (they're more likely to want to start from scratch so they can do things their way).
  • Focus on what matters. Don't start a project unless we can commit the resources to see it through. If we aren't willing to commit those resources, kill the project, because it clearly isn't important.

I can't emphasize enough how important this learning experience was for me personally. As hard as it was, I previously didn't have any discipline or plan when it came to growing the team. Since learning the above lessons, things have been great and I feel really confident in our plan.

What were your biggest advantages? Was anything particularly helpful?

I think that pretty much any advantage any business has can be characterized as something that the business can do that competitors can't or don't want to do. So whenever I think about how to compete with others, I start by trying to figure out what no one else is willing to do.

In the case of LACRM, I think our biggest advantage is the fact that we're willing to be patient. We don't have any investors breathing down our necks, we're not pushing for an exit, we aren't working so hard that we're on pace to burn out, and we're not looking for an early retirement. As long as I keep enjoying this journey as much as I have so far, I'm perfectly happy with the idea of doing this until I'm old (I'm 31 now). Despite there being dozens (or maybe hundreds) of CRM companies out there, virtually none of them are willing to be more patient than us. They're all sprinting, and we're running a marathon.

Why is this an advantage? It means that we can charge a bit less than maybe we should. It means we can offer better customer service even though it hurts our margins. It means that we can focus on word-of-mouth as our primary growth channel even though it's incredibly slow (but in the long run, it's much more resiliant). It kind of sucks seeing other startups leapfrogging us, but we're building a really strong foundation of happy customers that I think will be an amazing competitive advantage in the future.

But that's pretty general. There are definitely more specific things that have really worked out for us:

  • As I mentioned earlier, we stumbled upon the realization that having great customer service is a huge advantage. We win so many sales just because we're willing to pick up the phone.
  • Investing heavily in hiring has been great. Even at 11 people, we're already big enough that I by myself can't have much of an impact as an individual contributor, so making sure we hire awesome people is the most high-impact thing I can do.
  • Staying focused on really small businesses. VC-backed CRM companies always start out competing for us with the same customers, but inevitably it comes time for them to start scaling faster and that's really hard in this space. Those companies all go enterprise, and they leave the little clients to us.
  • Leaving San Francisco and moving to St. Louis. If you're raising money, the Bay Area is great. If you're bootstrapping, pretty much any city in the world is better. I think St. Louis is particularly ideal for bootstrapped startups (get in touch with me if you're interested in learning more about that).

What's your advice for indie hackers who are just starting out?

Figure out what you want out of this, and use that lens anytime you take advice from anyone (including me). The vast majority of startup advice is written by and for people who might not share your goals (like VCs for example), so it might be irrelevant, or even harmful for you.

Don't confuse fame with success. There are a lot of people in the startup scene who are well known but haven't ever really done anything. If you follow their lead, you may end up the same way. Unless your customers are programmers, getting a post on Hacker News won't matter. Being known by everyone at your local startup networking events won't matter. Winning a bunch of startup competitions won't matter. The way I see it, only two audiences matter: your customers and (if you have them) your employees. If you spend time trying to impress anyone other than those two groups, you're wasting time.

Develop the ability to quickly decide what matters and what doesn't. Whatever other skills you have will be multiplied by being able to apply them to the right things.

I don't read a ton of books (I mostly just stick to websites like this one) but I really enjoyed Startup CEO by Matt Blumberg and Traction by Gabriel Weinberg and Justin Mares.

Where can we go to learn more?

I love talking shop with fellow entrepreneurs, so please don't hesitate to reach out. You can reach me on Twitter, email, or in the comments of this interview.

If you're in the market for a CRM, you can check us out. We also have a blog, and you might be particularly interested in our bootstrapping posts (we're adding more soon).

  1. 1

    Hi Tyler. Thanks a tonne for sharing your journey and thoughts in great depth. Really loved every aspect of how LACRM looks at it's employees to its customers and relies on long term approach v/s right now model.

  2. 1

    Hi Tyler, great story! Congratulation on your success with LACRM.

    What do you think a bootstrapped startup should do if they want to go with the enterprise client too? Is it possible or should there be a huge differentiator like a niche location away for the competitor's location.

    1. 1

      I don't have a ton of expertise working with enterprise clients, so don't take my opinion too seriously, but here goes: I do think it's possible for bootstrappers to get enterprise clients, but there are some caveats:

      1. I think it's pretty common to start small and move "upmarket" to bigger clients. This is partially because you naturally start with a basic product which might be a better fit for small clients, but it's also because enterprise buyers are risk averse and might be more hesitant to work with a SaaS vendor that doesn't have a reputation yet.

      2. When selling to small businesses, product matters a lot. Their buying process is to try the product, see if they like it, and make a decision. In my experience, enterprise buyers normally won't even try the product until very late in the sales process (if at all). They want whitepapers, responses to RFPs, feature comparison checklists, and endless sales calls/meetings. So what I'm getting at is that if you want to go into the enterprise space, your most important core competency is sales. Not product, not tech, not marketing. If you don't have someone with enterprise sales experience, I personally would stay away.

      3. One of the reasons enterprise is hard as a bootstrap is that the sales process itself is long and expensive. Even if things go smoothly, you'll probably need a lawyer to get involved with every deal you make, and it could take months or years before you collect any revenue. So unless you already have some clients lined up (like if you're already connected with some enterprise customers and you know they'll buy from you immediately) you should have a plan for staying alive the first couple of years. You either need enough money saved up to covering living expenses and all the costs of making a sale, or you need another source of income (a different job, or potentially SMB clients for the same product).

      1. 1

        Awesome! I think you just saved me from directly going to enterprise without a lot of budget.

  3. 1

    Love the 'extend the free trial' until you have the billing system built out.

  4. 1

    Very inspiring, this is maybe my favorite interview so far and I read them all! Thank you for that different perspective on business, growing and revenue :)

    1. 1

      Thanks, I'm glad you liked it!

  5. 1

    Made me smile that using the phone was the winning tool, as the customers are talkative salesmen. KNOW YOUR CUSTOMER ®

  6. 1

    What is the thinking behind your unique/ kinda strange product name? Any benefits or challenges that come with it?

    1. 1

      It's definitely a polarizing name. Some of our customers hate it and tell us that, but most of the feedback we hear is very positive. Of course there might be some selection bias there.

      There are a few ideas behind it:

      1. When we started the company, we didn't know what our product would be, but we didn't want that to stop us from building a website and starting to think about branding. So we wanted a name that would describe what we think we're good at but that could fit almost any product. "Less Annoying Software" was the result of that. In the future, we'll probably make a number of different "Less Annoying" products, not just CRM.

      2. I get kind of frustrated by all of the nonsense names out there. I realize that it doesn't really matter much, but I wanted a name that actually communicated our value proposition clearly. It's long and hard to say, but at least when people here it they know exactly what we do.

      3. The CRM space is super crowded. In markets like that, I think it's better to do things that really speak to some people even if most people hate it. This applies to more than just naming. I don't want to be afraid to have personality and be opinionated because trying not to offend anyone isn't going to get any attention given how many other CRMs there are out there.

      But yeah, our name definitely isn't for everyone. It's particularly hated by people at larger companies who are embarrassed to recommend us to their boss. If we were going after the enterprise market our name would be terrible, but I think it works really well for the micro-businesses we target.

  7. 1

    Tyler, great interview. When your interviewing a new potential employee, what does the process look like? What qualities do you look for?

    1. 1

      Thanks! I don't think there's a way to give a short answer to this, so get ready for some rambling...

      The majority of hiring that I've done has been for our "CRM Coach" role which is basically all of the customer-facing jobs put together (customer service, customer success, account management, etc.) but we've also recently started interviewing a number of developers too. For both roles, we're basically looking for [1] overall intelligence, [2] mastery of the core skill (communication for a CRM Coach, programming for the devs), and [3] a sense of satisfaction from doing the job (helping people for CRM Coaches, building software for devs).

      1 and 2 should be obvious, but I think 3 isn't something everyone thinks about. If you hire someone who isn't intrinsically motivated to do their job then you have to provide external motivation. Like commissions, weird games with bonuses, and quotas. When you do that, the employee is just playing the game you've set up for them instead of just trying to do a great job. That makes management a lot harder and creates all kinds of potential failure modes. So whatever job we're hiring for, we want to make sure that the employee is the type of person who will find it rewarding. I've found that if you do that and then just don't get in their way, most people will really blow you away with what they can accomplish (side note: if you talk to people unhappy with their jobs, a lot of them will say it's because their boss gets in the way of doing a good job).

      Aside from that, we don't look for any specific characteristics. This is partially because we're hiring entry-level employees who haven't established much of a professional identity yet, and they're very moldable. As long as someone is smart and has a good attitude, there's a very good chance we can help them develop any other skills they need.

      As for the actual process, we have three stages:

      The first is submitting a resume/writing sample that we review. Even developers need to submit a writing summary (English, not code) because working with people who can't communicate well is just a nightmare in my experience.

      Second, we set up a Google Hangout interview which is about an hour. We go over some basic "are you a good fit for the job" questions and give them a few challenges (like for a dev, very simple coding questions that anyone should be able to ace). This is meant to be a really basic filter to make sure we don't waste anyone's time with an in-person interview for someone who's a terrible fit.

      Third, we bring them in for an in-person interview. That starts with some projects related to the job (a simple writing project for CRM Coaches, and some technical questions for developers). Then we have a conversation about software design. None of the people we're interviewing are designers, but we've found that it's a good way to get them to think our their feet and see how they communicate about tech. At that point we're done with the "interview" phase and it's time for us to try to sell them on the job. The candidate goes out to a neighborhood coffee shop with some of the people they'd be working with and it's their chance to ask candid questions without any bosses around. Then they come back and play a game of Pandemic (the board game). That might sound weird, but it's actually pretty great. If you don't know it, Pandemic is a cooperative board game for up to four people. So everyone's on the same team and it's a really interesting way to see what it's like to work with someone. Are they open to feedback? Are they afraid to speak up if they have an idea? I think both sides benefit a lot from that experience.

      The whole in-person interview takes about four hours.

      If we end up giving someone an offer after that (full-timers anyway, not interns usually) we'll have everyone on their team except the managers take them out to dinner just to really try to make them feel welcome and excited about the opportunity. We're almost always hiring people straight out of college who have no idea what they're looking for, so it's helpful for them to have plenty of chances to talk to other employees who were in the same situation recently.

      1. 1

        wow, thanks for taking​ time to answer. I have never heard of a board game being used before. I really like the dinner aspect.

        I do hiring at my day job from time to time, and I have always found it a challenge to find the right people.

        1. 1

          Any tips on things you've found helpful? We've put a lot of effort into our recruiting process, but no one at the company had ever hired anyone before LACRM, so I'm sure there's a lot of stuff we could be doing better.

          1. 1

            I had these written tests that I had developed over the years for technical interviews, but I came to see that they were not always the best indicator. Sometimes you have to be a little more flexible in the specific skills you need. What I do now is look for people that are hungry to learn, but they are fresh out of school. People that show initiative and a desire to learn are the ones I really like.

            Some good example indicators I look for are:

            1. a github account with some active projects
            2. a part time gig in some industry where they hacked together something to solve a business problem, sometimes this happens while they are still in school.
            1. 1

              Thanks for sharing. I really enjoyed your article. Finally i found someone that agrees with me for hiring strategies. I'm looking to hire right now and so it strengthened my intentions.

  8. 1

    Awesome interview. Question: How did you and your brother decide who would be CEO? What's his position now, and what was that transition like? I'm in a 50-50 partnership right now and I'm wondering what that might be like in the future. Thanks.

    1. 1

      It was pretty easy for us because my brother didn't seem to have any real interest in being CEO. As a matter of fact, I'm not sure we ever even explicitly had a conversation about it in the early days, it was just understood. When the company centralized in St. Louis, he decided to stay in Boston (he's our only non-Stl team member) which really solidified that while he's a very important individual contributor, he isn't really playing the role of a leader the way a co-founder might normally play. His primary role now is to handle DevOps for us, but he also gets involved in various other parts of the business (he's a great person to brainstorm with).

      Having said that, I understand that it won't normally be as obvious as it was for us. If that's the case, I'd suggest figuring it out early to make sure that both co-founders have similar expectations. It would be a shame to get through the really hard part at the beginning and then have the whole thing blow up because of a power struggle or hurt feelings.

      Also, I think it's important to understand that as the company grows, your fit for a particular role might change. Bracken enjoyed playing the role of a co-founder when we were smaller, but didn't like it as much as we started hiring people. I love being the CEO right now, but I'm learning as we go, and I realize it's possible that the company my grow faster than I can learn. I'd make sure that you and your co-founder are both open to the possibility of your roles changing down the line.

  9. 1

    Hey Tyler, thanks for the interview, I really appreciated it. I'd love to hear more about how you set up profit sharing to closely mimic equity incentives.

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      No problem! The two main things that we wanted to mimic from equity were [1] letting employees share in the upside if we end up being massively successful and [2] giving people who work here for a long time a way to continue to share in our success even after they leave the company.

      In our case, there are two different phases of the profit share. Right now, there are only four people who receive money from the profit share: the two co-founders and two very early employees who we weren't able to pay anywhere close to market rate when we hired them, so we needed to give them significant upside. The way it works is that I don't owe them any guaranteed salary, but everytime I pay myself, I have to pay them the same amount. This is a great way to align incentives. They know that they'll be taken care of in the long run, but it gives us a lot of flexibility in terms of deciding when and how to take money out of the business (note: this requires your ego to not require you to be the highest paid person at the company).

      Once all of the partners hit a certain income level, we enter the second phase which is a general profit share among all of the employees. We basically give each new hire notional "shares" in the company's future earnings. Once again, if I pay myself, that money gets split up according to shares. To give you an idea, each co-founder has roughly 30% of the total shares, and employees range from 5% down to .1% for brand new hires. We grant additional shares each year so that people who have been here longer can build up their stake in the company.

      Additionally, we came up with this idea we call "reverse vesting". When someone leaves the company for any reason, they are still eligible for the profit share, but their shares linearly drop off over the amount of time they worked. For example, if someone has 1000 shares and they worked here 10 months, then the first month after they quit, they'll be paid as if they have 900 shares, and then 800 the month after that. So if someone works here for a really long time, they'll have a very long reverse vesting period to mimic the permanent ownership of stock.

      Finally, if we ever sell the company, these imaginary shares turn into real equity. The only reason we're not giving out equity is because it doesn't fit our model, but if we exit, then at that point equity would be a perfect fit.

      Our employees know that this is basically a lottery ticket. Other than those two partners we brought on early, we pay everyone at least market salaries so that they don't need to rely on this profit share kicking in one day. But if we continue to grow to the point that we're a big success, this will be a nice way to make sure the rest of the team is taken care of.

      I hope that all makes sense! Let me know if you'd like any additional details.

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        Just reading this and I am blown away ... I will be reaching out to you at some point.

      2. 1

        Very cool. Thank you for sharing. That seems like a great way to align incentives when you don't foresee an exit. I love the creativity and thanks for the thorough answer.