With a career that spans dot-com booms, market crashes, myriad financial crises, and everything in between, Gregory Jones has earned his stripes. His career has seen him become the Senior Partner and Co-Founder of Edgewater Private Equity Funds, but more than this, he is a finance leader who built one of the original internet commerce success stories from the ground up.
As the former CEO and Chairman of UBid.com, Jones took the company from concept to IPO, scaling to nearly $500 million in revenue along the way. But if you ask him what really drives long-term success, he won’t talk about tech stacks, market timing, or the latest money hack that will make you rich quick. Instead, he’ll point to something quieter, more solid, and far more durable: foresight, discipline, and a long-game mindset.
This isn’t a man chasing quick wins. He’s someone who has spent decades refining a strategy built on clarity, patience, and good judgment. And it’s a strategy that anyone serious about investing can learn from.
Key Pillars of Strategy for Investment Success
It’s easy to get swept up in headlines and internet hype. But, according to Jones, good investing comes down to principles you can return to, time and time again, especially when things get bumpy. These aren’t tricks; they’re muscles that take time to build but bring strength and the ability to flex over the long term.
Informed Patience
Markets rise, fall, and get noisy in between. The instinct, especially when things look shaky, is to act. Jones, however, sees patience not as inaction, but as strategic stillness. He suggests that knowing when to move is less important than knowing when not to move, and that kind of patience only works when it is underpinned by research. Gut feelings help, but only if you’ve done your homework first.
So don’t think of investing as something you can jump into and start making big wins from day one. Success comes from experience, patience, and most of all, know-how.
Purposeful Diversification
It’s tempting to spread investments thin, hoping to cover as many bases as possible. Jones takes a different view. Diversify, yes, but only in areas you understand. Don’t chase sectors just because everyone else is going after them. If you don’t believe in the value or don’t understand the mechanics, you’re setting yourself up to panic when the winds change.
This kind of focused diversification requires conviction. It also means being comfortable missing out on a trend or two, a discipline many investors only learn the hard way. So, stick to what you know, and don’t be too distracted by the shiny new thing. All that glistens is not gold.
Relationship Capital
The best investors don’t just put money into markets; they invest in people. And sometimes the value of that investment is measured in time, insight, reassurance, and not money. For Jones, relationship capital is just as critical as financial capital. Mentors, partners, advisors– those connections compound over time, opening doors, providing second opinions, and sometimes stopping you from making costly mistakes.
Your network can be a risk filter. Sometimes the right conversation at the right moment can save you a million-dollar error, or encourage a million-dollar move. So, the more conversations you have with trusted people, the better.
Tech is a Tool, not a Crutch
From the latest AI models to dashboards and predictive analytics, there’s no shortage of tech causing a stir, promising sharper decisions, faster results, and curves to get ahead of. Jones is all for using tools, but not for replacing human judgment. Data and technology are helpful, but can also become a distraction. Recognize the tools for what they are, and use them to clarify your thinking, not to do your thinking for you.
That distinction might sound subtle, but it separates the wise from the overwhelmed. At the end of the day, it’s still the investor who has to decide what to do next and live with the outcome. Do you really want to outsource that control to an algorithm?
Lessons to Learn
No one gets it right all the time. Indeed, some of the most important lessons come from getting it wrong and learning to do better next time. The best investors all carry a few battle scars. What separates them from the rest is that they learn from the experience. They come back calmer, clearer, and a little more grounded.
Two big takeaways from Jones’ own experience:
- Always prepare for the downside. It’s easy to make plans when things go well. But resilience is built by asking what happens if they don’t. Jones doesn’t bet the farm. He stress-tests ideas, builds buffers, and makes peace with the fact that not everything will work out.
- Emotional control trumps technical skill. It’s not your spreadsheet that holds the line when the market tanks; it’s your temperament. Anyone can be taught to model a deal, but it’s much harder to learn how not to panic when things head south.
So, where does that leave the first timers, those looking to start their investing journey, and gain the experience and knowledge that will serve them for years to come? Jones has some small but powerful pieces of advice for anyone looking to make their first deals.
Advice to Aspiring Investors
Whether you’re a seasoned investor or just thinking about dipping your toe in the water, the same rules apply. And the sooner you internalize them, the better, because sometimes it’s your muscle memory that will keep you afloat and stop you from going under.
Start small – but start
You don’t need a big bankroll to begin. What matters more is consistency. A lot of people spend years waiting for the perfect moment—a moment that will never come. Better to start soon, start small, and keep the momentum going.
Don’t chase what you don’t understand
Hot tips are rarely hot for long. If you can’t explain why you’re investing in something in one or two sentences, you probably shouldn’t be investing in it at all. Don’t get caught up in the hype and excitement. Take a step back, observe the landscape, and stick to what you know.
Don’t confuse wealth with success
Money doesn’t buy happiness. But it’s a tool that, if used wisely, can certainly help you get there. Ultimately, the aim of the game is to build a life you’re proud of, where your financial choices reflect your values, not your anxieties. You can have all the money in the world and still be unhappy. It’s how you use it that counts.
Stay humble
Markets don’t care how smart you are. The minute you think you’ve got it figured out, the market will remind you otherwise, and there’s a real truth behind the saying “pride comes before a fall.” Discipline, clarity, and a sense of perspective will take you further than any shortcut.
Key Takeaways
Gregory Jones didn’t get to where he is by being the loudest voice in the room. He got there by sticking to a strategy built on self-awareness, preparation, and calm.
Whether you’re building your first portfolio or looking to refine your approach, the lessons are the same:
- Prepare for the downside
- Invest in what you understand
- Surround yourself with smart, grounded people
- Use technology wisely, but trust your judgement more
- Start now, stay consistent, and don’t lose your head
There’s no one-size-fits-all roadmap to success. But Jones offers something better: a compass to help you navigate your own path.
