Fyxer.ai is an AI-powered assistant that helps users reclaim hours of their day by managing their inboxes, writing replies, and taking meeting notes. But Fyxer didn’t start with AI. It started with a decade-long executive assistant agency that gave them a treasure trove of data and insight that became the foundation for integrating AI.
Fyxer CEO and Co-Founder Rich Hollingsworth joins Madrona Managing Director Karan Mehandru on this episode of Founded & Funded to share how Fyxer went from $1M to $10M ARR in six months with just 30 employees.
In this episode, Rich shares:
-
- Why great startups start with real-world pain
- How there is still room for disruption with email
- Why quality data matters more than quantity
- The PLG-to-enterprise playbook that actually works
- The rowing team mindset that drives their decision-making
Whether you’re a founder, operator, or investor, this is a masterclass in AI execution, startup focus, and scaling fast without breaking.
Listen on Spotify, Apple, and Amazon | Watch on YouTube.
This transcript was automatically generated and edited for clarity.
Karan: You and your brother Archie didn’t just stumble into this; you spent years in the trenches of this core problem before you made an AI product. So, walk us through that journey. What did you learn? What did that teach you, and how did that experience of owning an EA agency inform the blueprint for Fyxer?
Richard: The intention behind starting the EA agency, which we did in 2016, was to use it as a platform to build the AI solution, but we recognized the technology wasn’t there at the time. When GPT-3 came out, we realized that the technology was available, and we were ready to go, and we got together with our third co-founder, Matt, who’s our CTO, and drew from our executive assistant agency, a kind of data pool, and a series of customer insights that helped inform building the product, and eventually get us product market fit instantly when we released it. I’d say the main takeaway that we believe in the market is most people really underestimate the role of an executive assistant. They think that it’s about executing tasks, book me this meeting, schedule this appointment. Whereas in reality, the value of an assistant is determined by how proactive they can be for their boss. And so building a memory and a knowledge of the customer is the key to being able to unlock real value to the user. And we took that thinking from day one, and that’s why our product is A, built within the user’s existing workflow, and B, it’s built across the workflow. There are lots of point solutions in the market. There are very few products that are a full suite, and that we saw as an essential route to unlocking the real proactive value of an assistant.
Karan: When did you know that you hit product-market fit? What did it feel like, and what advice would you have for other founders who are still trying to find that first wedge that takes off?
Richard: So, there are two moments that I think about. One was after launching the product, we moved to San Francisco for four months, joined an accelerator, and during the course of that, we grew by eight times in four months.
Karan: Which is where we first met.
Richard: Exactly. I think looking back at it, we had hit product-market fit, but at the time, it didn’t feel like that. We were just pissed that we didn’t hit 10X, to be honest. The real moment that I felt it was at the beginning of this year, when I was speaking to a user, and they told me that we had saved them from getting divorced that year, and that’s when I knew that we were onto something.
Karan: So, as you look back, and you see this explosive growth that Fyxer has seen, what do you think are the scaling risks or missteps that you think were crucial learning moments for Fyxer, and potential pitfalls for other founders to avoid?
Richard: I think the biggest thing that we’ve gotten wrong, and I see it happening a lot, is people spend too much time planning what’s going to happen if their plan doesn’t work, thinking about what they do in that scenario, rather than thinking about what happens if their plan works. And at the beginning of this year, we grew from $1 million to $5 million in ARR in two and a half months, and we hadn’t planned for that outcome well enough. And so we saw, for example, our customer support response time go from five minutes to five hours, and we found lots of similar scaling challenges in the process of growing so quickly. And that was a lesson that we won’t make… A mistake that we won’t make again.
Karan: I can certainly resonate with the thinking around what if things go wrong versus what if things go right. So, that’s sort of what venture capital is all about, too, because we have to believe in the art of the possible. That makes sense to me. So, as you look at Fyxer today, you’ve got capital, you’ve got resources, you’ve got a huge market, and so you almost have infinite choices in front of you, and where you can focus your energy, and your efforts. How do you make the decisions on where you prioritize, what you prioritize? How do you focus the team on the things that potentially matter, the things that you need to do today versus save for another day? What is the framework that you use?
Richard: So, I think this is where we’re exceptional. We have the fortune of having a map from our EA agency so we know exactly what we’re building, but not only that, we know exactly how to build it, because we can see the workflows that have worked historically, and we copy them wherever we can. The mentality we have within the company is, so in 2012 the British rowing team were training for the Olympics. They eventually won the gold. And the question that would always be a challenge to anyone who suggested doing something new was does it make the boat go faster? And we obsess about our end user who is a 55-year-old real estate broker in middle America, and our job is to make their email experience better. If the new tech idea, or the new direction people want to take the company in, or the new user they want to serve doesn’t do that, then we just don’t do it.
Karan: I love that. I love the analogy, too, of the rowing team. One of the things I’ve noticed, now being involved in the company with you, has been that you’ve balanced the bottom-up PLG motion with a top-down enterprise motion. So, you’ve got a lot of pre-users that convert into paying users, but then you’ve also got some really large customers like EXP, and others. How have you done that? It’s typically very hard for a startup to manage, and get both of them right, but how do you manage the bottoms-up PLG usage versus the top-down enterprise deals sales cycles?
Richard: We knew that this wasn’t optional. This is essential that we need to capture enterprise deals if this is going to become a billion dollar revenue company, not just a billion dollar market cap company, but the vehicle in order to do that very quickly at scale is using the PLG motion for individual users at enterprise companies signing up to the product, us building critical mass in the organization, and then taking it to their leadership in order to sign an enterprise deal. And we’re fortunate in our founding team, we have that skill set, and my co-founder Archie, who ran that motion from day one, and we managed to land a $1.2 million contract within our first six months, but it was all generated from individual user signing up, it expanding across the company, and then us capitalizing on that opportunity.
Karan: In some ways, the North Star, the ethos around product experience, and onboarding really haven’t changed that much. It’s just the nature of the deals that are coming in both from in bottoms-up, and the top down.
Richard: Yeah, we think about the user in both scenarios as exactly the same person — that 55-year-old real estate broker in middle America could be working for a large organization, or could be an individual broker, but the buyer of the software is different. And so there’s kind of a sales motion around that, and an onboarding experience around that we’ve had to allocate time for.
Karan: So, I don’t think you can go a day these days not reading, or hearing about how AI is disrupting everything, how it’s innovating, and how AI has permeated every sector of society. So, if you think about all of the stuff that you hear, and read about AI, and specifically related to the market that you’re going after, which is productivity, what do you think most people get wrong, or what do you think most people believe about the future of AI in your space that you don’t necessarily believe?
Richard: The biggest one I think is when I look at what’s happened since GPT-3 was launched, everyone thought that by now email would be a solved problem, that AI would’ve taken this off of our hands. And the reality is that just hasn’t happened at all. I remember when we started Fyxer, everyone said, “Oh, Google are going to do this really well. Microsoft are going to do this really well.” But the current competitive landscape is there are no startups I know who have gotten over a million in revenue, and Google, and Microsoft, I don’t know a single person who likes the products that they put out. So, our view on why that is that people believe that its quantity of data is what gets you the best results from the model, not the quality of the data that you train it on. And we have over index on quality. And I would say that’s the biggest differential we have to the rest of the market.
Karan:
Hearing you speak about email reminds me of that Mark Twain quote, which is the rumors of my death have been greatly exaggerated. And I think people have been talking about the death of email for years now, and it just hasn’t happened. It’s in fact gone in the opposite direction where we’ve gotten bombarded with emails. Let’s come back to Fyxer’s growth, and it’s very rare to see a company go from one to 10 in six months, and I know what aspirational plans you have for the company this year. As you think about thinking about hiring, and building a team that can capitalize on that opportunity in front of you, how do you think about hiring? How do you think about the people that you bring in to Fyxer in context of the growth plans that you have, and are seeing in the company? Are there frameworks that you use? Are there specific skill sets you look for? Are there specific types of people that you’re bringing in to Fyxer? Who are the folks that work well versus not? So, talk a little bit about your hiring strategy.
Richard:
Yeah, I think hiring is the one place that we really invest in looking in the long term as much as possible. Day to day at Fyxer, we’re obsessed by execution, and we’re focused on how do we move the company forward in the next day, in the next hour, and the next minute. And we focus the company very strongly there. Hiring though, we try, and look out as far as we can, and I think about it across two dynamics. One is if we’re hiring an exact person, I want them to have been there done that before. And so all of the folks that we’ve hired in the most senior roles have been a part of businesses that have scaled to as far out as I can see the next three years for Fyxer. But the crucial component is they need to be willing to do the very unglamorous work.
So, when at the beginning of this year we raised our series A, we had a team of only four people, and I had the opportunity to build this with a blank canvas. And the first people that I hired were an exec team, which really was quite an unusual, unorthodox approach. And with that it meant that we could have senior leaders build out their entire teams, which is fantastic, but it required all of them doing the grunt work, if you like, in their first three to six months. And them wanting to do that is the biggest important component for them getting the role. And on the other side, we like to hire people with less experience, but with a real growth mindset. So, hiring for the slope rather than the intercept. I know, is a mental model that you have. We very much lean into that, really, because we like the naivety, almost, of people having not got a playbook for how to do something, for thinking as much as possible from kind of first principles.
Karan: Yeah, I think that’s great, and I love that, and I can see it apply to so many real realms of society, including your work, and my work where pattern recognition, and having seen the story helps you for the first call it 70 yards, and then that healthy level of naivety, and first principle thinking is where the real magic happens. And I’ve seen that pretty much every day in my interactions with you and the team. So, kudos to you on sort of living that philosophy. Let’s go back to something more personal. Not many siblings would even think about starting a company together, yet you and Archie have done that, and done that successfully. How has that relationship either helped your journey as a founder, and how did you guys meet Matt and bring him on as your third co-founder? So, walk us through a little bit of that personal story.
Richard: Archie and I actually grew up on a farm. So, the nature of a family farm is that work, and family life are kind of intertwined very, very closely. So, it always felt natural to us that we would work together, particularly because we have very complementary skill sets. He is a born and bred salesperson, and my role as CEO — I’m a real generalist, so it just fits very nicely. He also has a very low ego, so he doesn’t mind his older brother being his boss as well. And I think that’s quite a key component to making the dynamic work. The journey then, so in the process of building our executive assistant agency, we knew that we wanted to build it into a tech company, and Archie met Matt, actually at a poker game maybe four or so years ago, and Archie was convinced that Matt was the person who should help us build that. And the reason for that is he’s a born and bred product engineer, and so has a 360 view of the engineering team, and we knew that he was very sought after.
So, we knew that we needed a very, very compelling pitch in order to persuade him to join us. And this is someone who the former CTO of Stripe described as the most impressive future CTO he’d ever met. So, we knew that we needed something really compelling for him. And the way in which we did that was taking what was a 500,000-hour time tracking data set from our executive assistant agency that could tell Matt exactly what were the key workflows to build, and then we recorded the screens, or we had our assistants record their screens of the work they did so that he could map the exact workflows. And so our pitch to him was, join us for instant product-market fit. Join us because you have a CEO with experience in building, in company building, and you have a head of sales whose experience in delivering multi-million dollar enterprise sales contracts in this market was what kind of convinced him that we were the right people.
Karan: And having personally interacted with both Archie and Matt. Now, I feel like I definitely resonated to a lot of the comments that you made. Matt strikes me as one of those people who is a man of few words, but when he speaks, people listen, and so do I.
Richard: Yeah, that’s very fair.
Karan: And then Archie, I’ve often felt if there was a picture next to the word grit in the dictionary, it should have a picture of Archie on there. Great. Well, to finish us off here, how about a few rapid-fire questions, if that’s okay?
Richard: Yeah, sure.
Karan: All right. Well, what’s the one thing you’d wish you started doing earlier as a CEO?
Richard: I wish we had hired people earlier. We pushed it too far in the end of last year where the four of us at the time, so it was the three co-founders, and on one employee were working seven days a week, 18 hours a day, and I felt like we paid the price for that towards the end of the year where we didn’t capitalize on opportunities that we could have done.
Karan: Got you. This goes back to your earlier point of planning for success versus…
Richard: Yeah, yeah, that’s a good point. Yeah.
Karan: How do you see the AI system category evolving over the next two to three years?
Richard: I see startups winning it, and incumbents continuing to flounder. I think they’ve got so much… There’s so much disruption being caused by AI that it is redrawing all of the existing product categories that we have that the incumbents can’t help but protect their core businesses. And as a result of that, are going to be unable to innovate to the same degree that startups are, particularly when there’s as aggressive, there’s so much market pull that you’re able to grow a business much faster now than historically has been possible.
Karan: Definitely attest to that. What’s one founder skill that you find yourself learning right now? What are you working on in yourself?
Richard:
We’re fantastic executors. We obsess over doing the unglamorous work. We need to get better at promoting ourselves, and that’s one of my main goals for this year.
Karan: Well, welcome to this podcast.
Richard: Exactly.
Karan: Other than Fyxer, what is the one other AI tool that you and the team can’t live without?
Richard: I think this is probably the answer for 95% of people, but honestly, ChatGPT. I mean, our team relies heavily on tools like Cursor, but the one that they can’t live without is ChatGPT. I think that has found its way into everybody’s workflow and become more and more valuable, over the last year in particular. I’ve tried every other version, Perplexity, and Claude, etc., but I just haven’t found something that works quite as well as GPT.
Karan: I’m a huge fan of this podcast, Invest Like the Best, and they always end the podcast with this question. So, I’m going to ask you the same thing, which is, what is the kindest thing that somebody’s ever done for you?
Richard: I probably just think of my wife. She’s done lots of nice things for me over the years. Last year, she moved our life, including our newborn son, to San Francisco at the drop of a hat, literally within 24 hours of me asking her to move to San Francisco for four months. She just did it without question, because she knew that it was important to me, and that has paid dividends for my life and my career. So, I’m incredibly grateful for that.
Karan: That’s great. I get asked a lot of times, what is the biggest decision I’ll make as a founder and CEO? And I always tell people, the biggest decision that you’ll ever make as a human being is the spouse that you decide to spend the rest of your life with. And sounds like you made a really great decision in that. So, thank you for sharing that. Well, that’s all we have time for, but I am so happy and excited that you and I got a chance to talk. Really proud of our partnership. Really excited to see what the future of Fyxer has as we partner on this journey together, and thank you for sharing some of your minutes in the day with us today. Thank you.
Richard: Thanks, Karan.
Related Insights
