Outlander Series: Launching a Business and Hiring Remote Talent with Jonathan Twombly, CEO of Two Bridges Asset Mgt.
Outlander Series: Jonathan Twombly, CEO of Two Bridges Asset Mgt.
We are thrilled to launch the Outlander Series, where we explore the entrepreneurial journey of founders. Recently, we had the pleasure of sitting down with Jonathan Twombly, CEO of Two Bridges Asset Management, to discuss his experience starting and growing companies, and using remote talent to support his business. Jonathan is a Harvard and Columbia-educated historian, lawyer, and serial entrepreneur, fluent in Japanese and sporting a deep knowledge of all the best NYC watering holes. We sat down with him at one such establishment to learn how his adventure began.
How did your entrepreneurial journey begin? Was it after graduating?
Jonathan: Well, the desire to have my own business actually predated my time in graduate school. My first business was launched back in 2000–2001, when I was living in Boston with my brother. It was called Boston in Common — the idea was to help people connect offline through curated events and local experiences.
Obviously, we had a website to support it, but it wasn’t really designed as an online business. At the time, our web designer pitched us something that, in retrospect, sounds wild — he said, "What people really want is their own profile page, where they can interact with others, share updates, and build a digital presence."
And we thought, "That’s the dumbest idea ever. Nobody wants that," so we passed.
Looking back, we were basically staring at the blueprint for Facebook… three years before Facebook even existed. But we just didn’t see it — and we didn’t build it.
That was my first taste of entrepreneurship... Fast forward — I was a lawyer. I was a good lawyer, but didn’t enjoy it. It wasn’t rewarding. And I kind of bounced around. I would quit because I hated it, and then went back. I went to graduate school and then returned to law again.
But after the Great Financial Crisis, I got laid off — and I decided finally that I just didn’t want to go back into law anymore. That’s when I launched my first real estate business.
Going from law to real estate isn’t a typical path. What made you take that leap?
Jonathan: I was networking with a lot of people to try to find something in real estate. Honestly at that point, it wasn't like going straight from like being a lawyer to launching a business. I was really, at first, trying to find a job in real estate.
And that just wasn't happening, right? It was just—it was a bad time to be like a 40-year-old career changer trying to go into real estate with all these people on the street looking for jobs who'd been doing it for 20 years.
So I was doing all this networking and someone was like, 'Hey, I'll just be honest with you. The only way you're gonna get into this business is if somebody decides that they want to partner up with you for some reason.' And then, lo and behold, I met somebody who was like, 'Hey, I think you could raise money for me. Why don't we partner up? I'm starting this real estate investment business.'
And I was like, 'OK, let me think about it.' And part of thinking about it was, 'Well, OK... I don't really know how to evaluate you — whether you're like blowing smoke or not. So I'm going to introduce you to some of my friends who were like, financially sophisticated.'"
So I trotted her around — effectively, although I didn't realize it — it was kind of like a roadshow. I trotted her around to some wealthy friends, basically saying, 'What do you think? What do you think of this?' And she gave her pitch."
And they were like, 'Well, if you're going to join up with her... I don't know. But if you do, I will give you money. Like, I will invest money with you.' And it was a lot of money. It wasn't like, 'Hey, I'll give you $50,000.' I had a couple people be like, 'Yeah, I’ll give you $1,000,000 to invest if you do pursue this.'"
So I was like, “OK, I have this offer of partnership. I have at least two people saying they'll give me $1,000,000... maybe I should do this, right?” So that’s how I actually wound up with like my first customer before I even had a business.
What was the biggest challenge when you started?
Jonathan: Honestly, I had no idea what I was doing at first. I thought real estate was straightforward—buy properties, rent them out, and you’re set. But I quickly realized there was much more to it. I had to learn how to analyze properties, raise capital, and manage investments.
Who was your first client?
Jonathan: In real estate, my clients are my investors. Interestingly, before I even officially launched my business, I had already secured two investors. While networking, I introduced my business idea to some financially savvy friends, and two of them pledged $1 million each to invest if I moved forward. That gave me the confidence to take the leap.
What advice would you give to someone starting their own business?
Jonathan: One of the biggest misconceptions people have is fearing rejection from their existing network. Many believe they need to convince complete strangers to trust them, but in reality, the easiest way to gain credibility is by leveraging relationships with people who already trust you. Your network knows your skills and capabilities, and they’re often rooting for you. Don’t be shy about tapping them to help you get your idea off the ground.
What were some of the operational challenges you faced as your business grew?
Jonathan: Scaling wasn’t about hiring a large team for me, but I quickly realized that running a business requires handling a lot of different functions. Some of them I loved, and others I absolutely dreaded—especially anything administrative. Even though I’m not bad at it, I don’t enjoy raising money either. My strength lies in deals, not finance.
At some point, I had to accept that trying to do everything myself wasn’t sustainable. It’s easy to focus on the things you enjoy while ignoring the rest, but those neglected tasks eventually slow you down. It’s like dragging a wagon with only one working wheel. The only way forward was to start delegating—whether by hiring or partnering with people who complimented my skill set.
You mentioned working with a remote team. What challenges did you face, and how did you overcome them?
Jonathan: Finding the right person was the biggest challenge. I worked with several Virtual Assistant (“VA”) companies, but I kept running into the same issue: the assistants I was assigned weren’t capable of handling even basic tasks. At one point, I couldn’t even use the 10 hours per month I had prepaid, because there simply wasn’t enough, they could do effectively.
That experience made me question whether I really needed to delegate. But people kept telling me, “If you had the right VA, you’d delegate more.” Eventually, after trial and error, I found a VA who was a great fit. From that point on, everything changed.
The more we worked together, the more I realized how much I could offload. Even now, after years of working together, I still catch myself thinking, Wait, why am I doing this? My VA could handle it.
Getting into a good rhythm with a remote assistant takes time, but once you do, it’s a game-changer.
Does your VA use AI tools to support her work?
Jonathan: Yes, because I encourage it. She uses AI for things like generating transcripts, summarizing content, and even brainstorming post ideas. A big part of my business involves online courses and coaching, so having AI assist with summarizing recordings and organizing materials has been incredibly helpful. There are still a few things AI—or a remote VA—can’t do, like scanning physical documents, but overall, integrating AI into her workflow has made things much more efficient.
How has hiring a Virtual Assistant (VA) helped your business?
Jonathan: Hiring a VA was a game-changer for me. At first, I was hesitant, but once I brought in a skilled VA, I realized how much time and energy I was spending on administrative tasks. Now, I can focus on growing my business while my VA handles scheduling, client communication, and other essential tasks. It has made my workflow more efficient and scalable.
Final Question (before the lightning round): As an entrepreneur, there's often a new idea or business around the corner. What are you working on next?
Jonathan: In addition to running my real estate investment business and coaching program—which are very complementary—I’m currently in the process of launching a new venture with my wife: an immigration law firm.
We’re starting with a very focused niche, supporting Japanese families navigating immigration issues. I really believe that when you’re launching something new, it’s best to start small and specialized. It gives you clarity, makes your messaging sharper, and helps validate the concept before expanding.
The plan is to grow intentionally, with well-placed ads. As we gain traction, we’ll consider expanding into other areas of law or opening the service to broader communities beyond the Japanese market. For now, we’re in the early stages, but I’m excited about the potential.
Lightning Round!
What wins: distribution or product? I think distribution beats product. If you're not getting it out there, it doesn't matter how good of an idea it is. I learned that the hard way with my coaching business — people kept telling me I had the best program, but I couldn’t figure out how to sell it. Word of mouth doesn’t really help that much — you need to get out there and figure out distribution, or you get nowhere.
Where are you focusing your distribution right now?
For me, it’s LinkedIn. It used to be Facebook — at one point I had the biggest multifamily investing Facebook group out there. But then Facebook changed their algorithm and basically destroyed it. Now that group is worthless. LinkedIn is my go-to now.
What's one thinker or podcast that has influenced you?
Cal Newport. He writes about productivity and time usage — books like Deep Work and Slow Productivity. He’s really influenced me. I deleted almost everything off my phone. Now it’s just email and maps. It’s made me much more productive and also happier. If you’re in entrepreneurship, you have to read his work.
One productivity hack you swear by?
You gotta block your time. Everything should be on your calendar — especially the stuff you know you have to do regularly. For example, I used to hate doing investor reports at the end of the month, but I never scheduled them. Now they’re on my calendar, and I just do them without stress. It sounds small, but it makes a huge difference.
Where can people find you? LinkedIn. If you're interested in investing in real estate or learning how to invest in real estate, come find me there. Happy to start a conversation.
Final Thoughts Jonathan’s journey is a testament to the power of networking, adaptability, and leveraging remote talent. If you’re a business owner considering hiring remote workers, take inspiration from his experience—you might just find the perfect solution to scale your business efficiently with outland.work.
📢 Stay tuned for more interviews in the Outlander Series, where we explore the journeys of entrepreneurs who have embraced remote hiring.