A spotlight on Two Dots

Posted originally on the Next Play substack

These days, it is hard to have a conversation about technology and startups without at least mentioning AI.While inspiring demos are exciting (and often entertaining), they do not always directly translate well into practical business use cases.

And that is where technologists seem to often go wrong: they get very excited by a technology and start applying it everywhere, only to realize much later on (after spending lots and lots of money and time) that they were never really solving a real, valuable problem.

And so if you are looking to start an “AI-company,” or considering joining a startup that leverages AI in one form or another, you will really want to dig into understanding product-market fit.

Just because something has “AI” in the name does not necessarily mean it is, or will ever become a great business. You will want to try to avoid getting distracted by the shiny vision and magic-seeming technology before you first understand some preliminary questions, starting with perhaps the most important one: Is this company solving a real problem? (And, a fast follow-up, are they doing so in a way that is or will ever be commercially viable?)

If the answer is no – it does not mean that the business is a non-starter, but it should probably prompt you to at least think deeply about how much risk you are open to taking with your next play (TL;DR twitter demos do not equal long-term value).

Steve Jobs may say it best when he discusses this dynamic: "You've got to start with the customer experience and work backwards to the technology. You can't start with the technology and try to figure out where you're going to try to sell it.”

While there may be more quantifiable measures, it feels like “sensing” true product-market fit can sometimes feel pretty obvious from just one conversation with a founder. You can meet a CEO who is excited about describing their technology, which often feels high-level and not very satisfying, and then you can meet a CEO who is just visibly grinning ear-to-ear as they describe their upcoming (jam-packed) week speaking with dozens of new customers and working with their teams to continue shipping helpful solutions.

Meeting with Henson Orser, the CEO and co-founder of Two Dots, was an amazing example of the latter—a founder who is very clearly zeroed in on solving very specific, very valuable problems for paying customers.

He and team have built an AI agent that automates the end-to-end consumer underwriting process. Tangibly, they started by first focusing specifically on multifamily real estate managers, who needed help underwriting consumers while reducing fraud. They then built a solution that solved a very real, very valuable problem for their customers. The reslut? On average, Two Dots helps their customers save at least $2 million a year for every 10,000 units. This is what can happen when you take a meaningful, tangible problem (underwriters struggling to efficiently underwrite tenants because it is such a manual and fraud ridden process) and obsessively focus on building a very clearly valuable solution (TL;DR they built automations to orchestrate the entire underwriting process including income and employment data, credit scores, etc.).

Yes they have a very bold long-term vision (to reshape consumer financial services) and a thought around how to get there—but at the same time they realize that no long-term vision is possible unless they execute on delivering value in the short-term. And so that is exactly what they have done—prioritize the areas that matter most to the customer (and subsequently, watch as the company’s revenue rises).

Coming off a recent Series A, Two Dots is an interesting example to anyone A) looking for a company to join (they are hiring for nearly every role!) and B) thinking about how to leverage AI in ways that actually drive business value.

In this Spotlight, we try to understand: What is it like to work at Two Dots? What is the culture like? What are the interesting behind-the-scenes details that really drive the company forward?

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If you read the introduction, then you will not be surprised to hear what we saw as the unifying aspect across all of the people we spoke with at Two Dots: a commitment to (quickly!) solving real problems for customers. And yes, the word that stuck out to us was real—everyone at the company wants to make actually useful products (not just fancy demos).

The result of this focus on “making things people want” (yes Two Dots did go through YCombinator) is that many people on the team have commented on just how clear the product-market fit seems to be.

• “I've seen the immediate relevancy and desire from our ICP for a product that solves the specific issue that our system does.”
• “Two Dots is a "must have" product -- it basically sells itself. It's a rock solid business case.”

Revenue is growing faster and well beyond what many early employees expected.

• “I have been positively surprised by how flipping fast we have grown. I joined the company a year after its inception and the speed at which we have grown has been insane.”

And so to keep up with all this demand they are seeing, the Two Dots team seems to be pretty ruthless about prioritization. To put it another way—they care deeply about getting things done.

• “We actually make money and have PMF. It's time to scale and execute, execute, execute.”
• “Ideas don't really matter. Completed projects do.”

And so they have built a culture that in many ways seems designed for people who are good at (and enjoy) getting things done.

There is very little wasted time, mainly because it is hard to rationalize wasting time when you have customers banging on your door (or in this case filling up your Calendly links).

• “Meetings are rare. There is no bullshit and we get the meetings over with efficiently and quickly.”
• “The best thing: almost no meetings. We literally just have two meetings regularly scheduled each week.”

The Two Dots team recruits people that enjoy the challenge of working through complicated problems.

• “Your job is to find problems, think through how to solve them, then solve them end-to-end.”

They are big fans of creative problem solving, and encourage one another to come up with whatever solution feels like it will be effective (as opposed to just accepting the status quo).

• “We were trying some really out the box recruiting ideas and decided to throw a party during tech week, but got way more interest than we expected because we opened it to the public. We had to last minute recruit a bouncer or security person to assist. And we always love working with the best, so Max and I walked over to Jameson's, a local Irish bar, and found the most qualified bouncer, checked that he was off the next day, and hired them. It is a small story that encompasses what Two Dots is all about - ridiculously fast problem solving.”

Most of the people at the company today did not come from a property management background. And so many current teammates mentioned how there’s a rather steep learning curve to really understanding all of the details. They want people who are excited by the challenge of climbing that learning curve, and coming up with fresh ideas in the process.

• “It's important to listen to team conversations at lunch and in the team meetings to pick up new problems.”
• “My best advice would be to prioritize learning as much about the product, and the property management industry in general as possible.”
• “People who can't figure stuff out on their own and are not willing to dig in and solve problems will have a hard time.”

Two Dots is in a particularly interesting situation—they have product market fit but the company is still small enough such that everybody seems to understand the entire business. These sorts of situations tend to be good fits for entrepreneurial people who can think outside of their job description every so often and simply prioritize things that’ll make a positive impact on the business (as opposed to worrying too much about bureaucracy and departments).

• “We do an all hands to go over company health (it's very good) about once a month.”
• “I think it's at a perfect stage to join. It's a YC Series A company that's found its legs and has great product-market fit, while having a lot of room to grow and make its mark.”
• “We are still at a stage where you can have a meaningful impact and help shape the future of the company. If you’re looking for an opportunity to grow, take ownership, and be part of building something special, this is a great place to be.”

It is also still small enough where everyone knows each other. The team works in person in San Francisco, and spends *lots* of time working hard together.

• “We're all intelligent individuals that have high expectations for our careers and work ethic, but we also prioritize getting to know each other to the point where we're all genuine close friends. It's extremely important to us that our future hires are easy to get along with as being a small team, we spend a lot of time together, and it makes work feel like it is not that....work, when you're with people you like/care about.”
• “I also really enjoyed joining everyone for the holiday party before I officially started. It was a fun way to get to know the team in a casual setting, and it made me feel welcomed and excited to be a part of Two Dots.”
• “Just overall hanging out with my colleagues has been awesome.”

Everyone at the company still interfaces with the co-founders on a regular basis: Henson and Max. People have really *uniquely* great things to say about what that experience has been like:

• “Our cofounders/leadership team made this company their lives. They all left very successful careers to start Two Dots and are not about to let our initial success flounder. Sometimes I feel as though our CEO does not sleep with how much work he gets done. It's motivating to witness.”
• “The founders are extremely nice to work for, and the culture is positive and great. I wish I found a company like this earlier instead of working for FAANGs or mid-size companies.”
• “Henson is great at talking to people and checking up on people and being a people person! He's always so positive (almost like golden retriever energy?). Max is also super funny and really matter-of-fact without being cold. Very fun and playful and also effective. It's amazing how much breadth he has technically.”
• “Leadership at Two Dots is approachable, focused, and clear on the company’s vision. They balance strategy with day-to-day execution and give people the autonomy to do their best work, while offering support when needed.”

Two Dots is hiring across engineering, sales, operations, and finance. They work in-person in their San Francisco office. You can learn more and apply here.

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