Taylor Matthews of Farther on Startup Risk, Wealth Tech, and the Power of Long-Term Thinking

Builders & Buyers is dedicated to showcasing leading figures in the fintech industry and their contributions. Through candid and in-depth conversations, Stifel Bank’s Managing Directors, Josh Dorsey and Jake Moseley, aim to connect audiences with the thought leaders driving the future of finance. The series will explore personal journeys, company building, investing strategies, and topical macroeconomic conditions.

Notes from Josh Dorsey, conversation moderator:

Some founder stories are full of big pivots and flashbulb moments. Taylor Matthews’ path feels different—steadier, more intentional, and grounded in clear thinking over time. He doesn’t chase hype. Instead, he builds what lasts.

In this edition of Builders & Buyers, Taylor opens up about how Farther came to be, what today’s clients really expect from wealth management, and why trust—not tech—is still the ultimate differentiator. We talked about everything from risk tolerance and AI tooling to his earliest ventures (spoiler alert: selling backyard dirt made the list).

There’s a steadiness to the way Taylor thinks and leads that feels rare, especially in a space that often rewards noise over nuance. When he talks about building systems that truly serve people, it’s not just convincing—it’s compelling. I’m excited to share our full conversation below.

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Josh: I like to start these conversations with something fun. What’s a habit or hobby your colleagues would be surprised to learn about?

Taylor: Some might be surprised I play guitar, albeit poorly. I can handle most campfire songs. I’m not much of a singer, but I enjoy it. It’s something I loved when I was younger and still carry with me today. Mostly, the guitars just gather dust on the wall these days, but I still like to pick one up now and then.

If you could teleport yourself anywhere in the world for a weekend, with zero responsibilities, where would you go and why?

It would have to be somewhere warm. I usually try to go kite surfing when I have time off. So, ideally, somewhere with steady wind during the day but still warm and relaxing at night. A remote island in Polynesia or somewhere far like that sounds pretty ideal.

Let’s go back to the beginning of your founder journey. Was there a defining moment when you realized you wanted to start something of your own?

I don’t think there was one single moment. I’ve always been somewhat commercial. I remember trying to sell dirt I dug up in the backyard to my neighbors as a kid. I sold popcorn as a Cub Scout. I even ran a lawn care business. So, I think that mindset was in me early on.

I also often felt like I could do at least as well as some of the leaders I worked under, but I needed time and experience to build that confidence. I worked in investment banking, in a corporate strategy group, and at a couple of startups. One of them was a venture I co-founded that distributed tech-for-development products in Southern India, which was a huge learning experience. Then I joined another startup as employee #10 and helped grow it into a substantially larger company. I definitely was always going to build something. It was just a matter of when and what.

As someone who’s been in the early-stage trenches, has your view of risk changed? Or are you just more comfortable with uncertainty now?

I also defrayed some of that risk by marrying the right person. My wife has been incredibly supportive. She contributed great ideas to Farther and out-earned me for much of our careers. She was the ballast; I was the lottery ticket. So yeah, find the right partner and listen to the market. It’s probably a lot less risky than it seems.

How do you define success?

Success is really hard to define in universal terms. I think it has to come from within. If you’re creating value and doing something that makes you happy, that’s success. The more internally defined your metrics are, the more likely you are to be content. If you’re chasing external validators like titles, accolades, and status, it’s much harder to feel fulfilled

Let’s talk about Farther. When you talk about the company with people outside of work, how do you describe what it is and why you built it?

It’s always a little tricky because there’s a client side and an advisor side to what we do.

At its core, Farther is a wealth management platform. We’re a tech company that builds software for financial advisors and their clients.

For advisors, we make their lives a lot easier. We take the operational burden, like admin, trading, and rebalancing, off their plates and move it to technology or to support teams empowered by technology. That lets them focus more on their clients.

On the client side, the goal is to deliver a family-office-level experience. That means bringing every aspect of their personal finances together in one place and making everything work in sync.

Why do you think the world needed Farther when you started building it?

When I talked to financial advisors—whether at large banks or running independent firms—they all said the same thing: they were spending way too much time on operations and admin work.

If you look at industry metrics, about 70% of an advisor’s time is spent on back-office tasks. It seemed like something technology could fix. But the tech that exists in the space is outdated. Most of it is not even cloud-native. It’s hard to build on, and full of tech debt.

We saw an opportunity to build a modern platform from the ground up using today’s technology stack and to give advisors a better way to work. That efficiency translates into a better experience for their clients.

There’s a lot of conversation around the great wealth transfer. How do you see generational attitudes toward money changing? Has that influenced how you build Farther?

That wealth transfer is huge. Some estimates say around $100 trillion will shift over the next couple of decades, and that includes liquid assets, real estate, and company ownership.

That’s massive, and financial advisors are in a great position to help navigate that transition if they have the right tools.

Generationally, younger people expect more from technology. They want transparency, control, and ease of use.

Your platform blends technology and the human side of wealth. How do you think about that balance, especially given the emotional side of money?

That’s really the essence of what we’re building. We want to help advisors focus more on the emotional side of the business—the human connection—and less on the transactional stuff.

There’s a study from Vanguard that estimates the value a financial advisor adds to a client account is about 3% per year. Most of that comes from behavior coaching, such as helping clients stay calm during market volatility and make long-term decisions. The rest comes from things like tax strategy and portfolio optimization, where technology can play a big role.

If we can automate that technical backend, advisors can scale and deepen their client relationships. Take daily rebalancing, for example. It can drive better after-tax returns, but it’s nearly impossible to do manually. We can automate that. Our value is making the emotional work possible by taking care of the rest with technology.

I’m curious about tech design. A lot of the younger generation starts with apps like Robinhood or Greenlight. How do you build something that feels familiar to them, but also works for more complex wealth planning?

You have to meet people where they are. Younger users expect a modern, consumer-grade experience, like what they get from Spotify or Uber. But the finance space has mostly failed to deliver that. And even when it has, those tools often fall short as people’s lives get more complex with things like marriage, kids, homeownership, and multiple investments.

That’s where we come in. We provide that modern, intuitive experience, but with a human advisor layered in. Interestingly, Gen Z and Millennials are actually more likely than Boomers or Gen X to seek out financial advice. They value expert input. So, it’s not about replacing advisors with technology; it’s about enhancing the experience with tools that feel natural and easy to use.

How are you thinking about AI at Farther?

Most of our work so far has been on internal automation—helping advisors, operations, and service teams do more. There’s still a lot of paperwork in financial services. Automating that makes everything faster and more seamless.

But we’re also building advisor co-pilot tools. Imagine being able to query all of a client’s financial data instantly and spot changes, identify opportunities, and flag risks. AI can surface insights that otherwise would’ve gone unnoticed.

And of course, we use AI for mundane tasks like note-taking, summarizing meetings, and storing data. That’s all helpful, but not the most differentiating. The magic is in surfacing financial insights that advisors can act on.

Where do you draw the line between what AI can do and what should stay human in financial advising?

It starts with the advisor. Some people are comfortable doing things on their own or with minimal tech guidance. That can work for lower-complexity or highly sophisticated clients.

But as your situation becomes more complex or if you want to be more hands-off, a human advisor becomes critical. AI can enhance both ends of that spectrum, but fully replacing the advisor, especially when real wealth is at stake, just doesn’t make sense. The trust, judgment, and personal connection a great advisor brings can’t be automated.

Let’s shift to leadership. Are there any personal philosophies or mental models that guide you when making difficult decisions or facing uncertainty?

Like most people, I’m influenced by my upbringing and background. In meetings, I try to speak last and listen carefully. Especially when facing uncertainty, I try to weigh the probabilities on both sides of a decision because, usually, there are valid reasons to go in either direction. I also try to zoom out and ask: “Will I regret this later?” That lens often helps clarify the right choice.

And when there isn’t a clear answer, do you use a particular framework or set of questions to work through it?

It depends on the decision. But I often come back to first principles.

This is a trust-based business. If something could undermine the trust our clients or advisors have in us, we don’t do it. That’s a clear line.

Then I ask: How does this impact the business financially? Culturally? Strategically? Does it align with where we want to be in five or ten years?

Once you layer in those inputs—ethics, economics, culture, long-term goals—the best decision usually becomes clear, even if it’s not obvious at first.

What’s a mistake you’ve made as a leader that turned into a valuable lesson?

I make mistakes all the time and try to learn from them. Sometimes, what looks like a great short-term decision, like launching a feature quickly or working with a new partner, turns out to be shortsighted. You end up having to rip it out and rebuild it later.

People-wise, I’ve also made the mistake of seeing the best in everyone and hoping they’d deliver, even if they don’t have a clear track record. Over time, I’ve learned to put more weight on experience and past results.

Zooming out a bit, are there any books or thinkers that have shaped how you lead?

I was a philosophy major in college, so I could go on for a while. But more broadly, that rational training helped me a lot. It shaped how I solve problems and think through leadership challenges. My emotional range is pretty constrained—I like to joke I run from 4 to 6 emotionally, while my co-founder runs from 2 to 10. We balance each other out.

I also take a stoic perspective. I step back and imagine observing the situation from the outside. How would the lead character in this story respond? That mindset has served me well.

Would you encourage your kids to study philosophy?

Absolutely. I wish they taught more of it in high school. It’s basically training in how to think. Whether you’re solving a math problem or writing a story, philosophy helps you approach it more clearly and rationally.

Let’s switch to capital raising. You’ve brought on some impressive investors. What’s something you’ve learned about fundraising that you wish you’d known earlier?

The biggest surprise was how much of it is driven by narrative. I used to think it was all about the metrics.

I remember one raise early on. We had just grown 11x in the previous year, so I thought, “This is going to be easy.” It ended up being the hardest raise we’ve done.

The problem was that the numbers were strong, but they looked like they belonged to a different kind of business than what we were actually building. We had to reframe the story to show how our traction was a signal of where we were going, not just where we were. Once we did that, things started to turn around. But it took a while to learn that lesson.

How did you get better at telling the story?

Practice. Telling the same story over and over. Early on, I relied too much on slides. I’d go through the deck, thinking that would carry the pitch.

Here’s a painful example: I pitched a big investor group over Zoom on a Monday morning during COVID. I thought it went okay. Later, the investor who brought me in said, “Taylor, you’ve got one of the most interesting models we’ve seen, but you weren’t interesting in that room.”

That stung, but it was great feedback. It forced me to rethink how I showed up and told our story. I’ve never forgotten it.

For any investors reading this, honest feedback like that is incredibly valuable. I know it can feel risky to share, but founders genuinely appreciate it.

You’ve already dropped a lot of wisdom, but do you have any specific advice for a first-time founder raising from institutional investors?

Bring people along for the ride. Help them see the world you’re trying to build. Paint the picture—what does success look like, and how does the world change if you get there?

Investors want to believe in that vision. Show them you’re the right team, with the right traction, solving the right problem. Tell it as a story, not just a spreadsheet. If you can do that, you’re already ahead of most. I wish someone had told me that earlier in my career.

What do you think people often misunderstand about building, managing, or passing on wealth?

The power of compounding. People just don’t appreciate how much small percentage differences can matter over time. There’s a quote often attributed to Einstein: “Compound interest is the most powerful force in the universe.”

It’s so easy to get caught up in day-to-day market moves or short-term wins. But a long-term strategy, executed consistently, will usually outperform. Even very sophisticated people struggle with sticking to the plan.

What advice would you give your 18-year-old self?

Don’t expect everything to happen quickly. You’ll wildly overestimate what you can accomplish in a year and underestimate what you can achieve in ten. Long-term persistence is underrated.

If you walked away from Farther tomorrow, what would you do next?

I’d probably go kite surfing on that Polynesian island first.

But honestly, there’s still so much I want to do here. So much value to unlock. It’d be hard to walk away unless something really special came along.

Stifel Bank is not affiliated with Farther.

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Beyond the interview:

• LinkedIn
• Website

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