Glen Smith built GDS Wealth Management into a much larger wealth management firm by relying on the advantage he knew he could control: how hard he worked. But leading the company’s next chapter asks something different of him.
Early in Glen Smith’s career as a financial advisor, his wife suggested he get a second job pumping gas at Costco. He was in his early 20s, earning very little, and she was earning considerably more.
Her idea was to keep building the career he wanted during the day and pick up another job at night to close the difference. Glen remembers wrestling with the choice. He was supposed to be advising people about their money, and he could picture one of those same clients pulling into Costco and finding him at the pump.
But he knew she had a point. So instead of taking the second job, Glen decided to put even more time into the one he already had.
That default response of working harder would follow him for years.
If you’ve built a company from scratch, you may recognize the instinct: when something feels shaky, do more. Stay later. Carry it yourself.
Effort helped Glen close the gap
Financial advising wasn’t an easy field for Glen to break into. Several firms passed him over because he was 22 and didn’t have the experience they wanted, until A.G. Edwards finally gave him a shot.
Once he got there, Glen immediately noticed the advantages other new advisors seemed to have. Some had better networks, better credentials, or family connections in the industry. Glen was still learning the basics.
He remembers wondering how he was supposed to compete with someone like that. His answer was to work longer.
If somebody else arrived at eight, Glen could be there at six. If they went home in the afternoon, he could stay into the evening, and weekends gave him more time to make up ground.
“All I had was effort,” Glen remembers.
At that point in his life, the fear of failure weighed heavily. He didn’t come from money, his wife didn’t either, and once they had children, Glen remembers thinking about something as basic as how he was going to provide diapers for his newborn.
Working harder gave him a way to answer that fear. And for a long time, it worked.
The same instinct was starting to cost him
The more Glen built, the harder it became to switch off the instinct that had gotten him there. Clients were counting on him, and every new level of responsibility seemed to raise the cost of letting something slip.
That pressure came home with him. Glen remembers working six or seven days a week for years, not for a short season, and says the business came close to costing him his marriage. Client problems kept him up at night, and when each of his children was born, he returned to work the same day.
He understands now how stark that sounds, but at the time, the fear of not providing felt more immediate than the possibility that a few hours away might not matter.
He sees that choice differently in his mid-40s.
Early-stage businesses can face real consequences when the founder is the only person available to handle everything, but Glen has become more conscious of the sacrifices he’s making and why.
Where does that leave you if the pressure that once kept the business alive becomes the way you lead by default?
Glen wanted to build GDS differently
By 2017, Glen had built a successful career at Merrill Lynch, but he had also developed strong opinions about how he wanted clients to be treated. Walking away meant leaving roughly $1 million in deferred compensation behind, and Glen expected his income to fall substantially.
He went anyway.
Part of the decision stemmed from discomfort with the brokerage model he had experienced, including pressure to use proprietary products. Glen believed there was another way to build a financial advisory firm without putting those incentives ahead of the client.
He sometimes describes his philosophy as being “long-term greedy.” Do right by the client over time, he believes, and the business will be better for it too.
The new firm also gave Glen the chance to create something he hadn’t fully realized he wanted until later: the kind of place he wished he had entered when he was younger.
Glen never had much of a mentor early in his career. He had sales scripts, but he didn’t have someone showing him how to grow into the profession or giving him a place to bring the questions he couldn’t answer on his own.
The brokerage culture was intensely competitive. Other advisors could feel like people you hoped to beat instead of people you could turn to for help.
At GDS, Glen wanted colleagues to work together. If a client needed expertise someone didn’t have, he wanted the advisor to be able to bring in another person from the firm without feeling as though they were giving something away.
There was some irony in that vision. Glen wanted a company where people could rely on one another, but he had spent much of his own career learning to rely on himself.
Learning to trust people took more than one try
When GDS was small, there wasn’t much choice. Glen answered the phones and opened accounts because the work still had to get done, and years of handling so much personally gave him a very specific picture of how he wanted things done.
The trickier part came when the company grew large enough that he didn’t need to carry it all.
That’s a hard question for a lot of founders: When does stepping in stop being helpful and start keeping everyone else from fully owning the work?
Glen didn’t immediately find the right people for his team. Some early hires didn’t work out, and that gave him plenty of reason to keep believing he was safer handling things himself.
Then he hired Erica, a client associate who is still with the company today.
Over time, experiences with high-performing team members like Erica showed Glen that handing off responsibility didn’t automatically mean watching the standard fall.
He realized he needed someone beside him at a broader level too. That led him to Robert, whose personality is noticeably different from Glen’s. They brought different strengths to the business, and that difference helped. Some areas suited Robert more naturally, while others fit Glen. Together, they could cover ground that neither of them would have handled as well alone.
Building a team didn’t have to mean finding another version of himself.
Today, Glen is figuring out where his time belongs
Glen has already changed a lot about how he leads. He has built a firm where people collaborate, brought in leaders with strengths different from his own, and learned that handing off responsibility does not automatically mean lowering the standard.
But the next stage of GDS is asking for another kind of change.
GDS has grown far beyond the days when Glen was answering the phones himself. The firm now manages roughly $1.8 billion, and Glen still carries significant responsibility within the company.
He serves as CEO and CIO and is effectively doing much of the COO work too. Operations are work he understands well enough to step into, but he doesn’t consider them his strongest area or where he wants most of his time to go.
Glen’s instinct is still to notice what isn’t right. He knows how he thinks the work should be done, and when he sees something miss the mark, staying out of it doesn’t come naturally.
His biggest need is stronger operational leadership that can carry more of the company without handing every important question back to him. He also wants GDS to remain within the business itself, rather than disappear when a person leaves.
The firm has figured out many of the right ways to operate. Now the focus is on making those ways repeatable without forcing him to keep every detail in his own head.
If you’re leading through a similar stage, a few questions are worth sitting with:
- How many decisions still come back to you because everyone knows you’ll make the final call?
- Where are you stepping in because the work truly needs you, and where are you stepping in because you’re used to being the safest pair of hands?
- If you disappeared for a week, which parts of the business would immediately feel your absence?
Letting go is harder when you still care deeply about the details
Glen has spent years holding himself to a demanding standard. He cares about how clients are treated when they walk into the office and how the work behind their financial plans gets done.
He also admits that he has a hard time letting go of mistakes when he believes they could have been prevented. When something falls short because somebody missed a detail, he can carry that frustration with him.
For years, personal involvement was how Glen protected the standard. If he knew exactly how he wanted something handled, doing it himself removed a lot of uncertainty.
Now he’s trying to separate caring about the result from personally controlling the work behind it.
That may be one of the hardest changes for someone who spent so much of his career believing that being willing to do more was part of what made him valuable.
Glen doesn’t expect himself to stop noticing when something is wrong. He jokes that if someone executes a detail badly, he’s still going to point it out. He just doesn’t want to be the person executing every detail anymore.
How much of your own identity as a leader is still tied to being the person who catches the mistake, fixes the problem, or knows the answer first?
Glen is still ambitious, but he sees the tradeoffs more clearly now
Glen’s plans for GDS aren’t modest. He talks about taking the company national and envisions building a much larger organization in the years ahead.
He also thinks about the younger advisor somewhere out there who is hungry enough to work the way he once did. Glen knows that person exists because he used to be him.
Twenty-five years ago, he was sitting in a training class, wondering how he could compete with people who seemed to have more going for them. His answer was to arrive earlier, stay later, and refuse to be outworked.
That mindset helped build his career, and Glen doesn’t dismiss the role it played. But he also knows now that the cost wasn’t limited to long hours.
What would Glen tell the younger version of himself? Be more present with his wife and kids, and don’t go so hard on himself when he got something wrong.
Being patient with yourself or others doesn’t have to be lowering the bar.
That may be the most personal change underneath everything happening at GDS now. Glen still wants more from himself and from the company he built, but he’s learning that neither one has to depend on him carrying quite so much alone.
And if that idea makes you a little uncomfortable, it may be worth asking why. Are you still leading for the company you have now, or for the version of it that once needed you to do everything?
To hear Glen go deeper on building GDS, learning to rely on other people, and the leadership work still ahead of him, listen to Episode 23 of the Hitting the Ceiling podcast.
For more ideas, questions, and lessons from inside the Visionary seat, subscribe to Mark O’Donnell’s Clarity Break Thoughts newsletter.
