How I Manage My Career & My Team As A Founder | Winning In Entrepreneurship

Hello everyone, welcome to our new interview for this week! Here are the questions:

What do you consider to be your greatest professional achievement?

As an entrepreneur, there’s this defining moment that most entrepreneurs have where they’re like, I finally made it after all the hard work and the blood and the sweat and the tears. 

This is the exact moment where you can finally accept that the business that you’ve been working on and the things that you’ve been pouring hours into have turned the corner in a way where the business is now a sustainable, self-sufficient, successful, business. 

We had multiple companies, but they’re all intertwined and they were working synergistically and it was a ton of work, but it was just this moment that we knew things had clicked in and the money was following the systems and the team that we had built from that point on. Now also at this moment, what really helped is that we were hitting about a million dollars a month in sales with a huge margin on it. 

So by almost any account of business, we were having really successful, healthy, happy months. So that was my first big win as an entrepreneur knowing for certain I could build a business, I could build a team, we could train our team and we could make some serious money in a competitive business. But the problem was just like meeting great things. There’s a trade off for that and because we had so much rapid growth and because we built the team a certain way, which is what the company needed from our experience at that time, the problem was it was not sustainable. The flip side of it was I was pouring myself into the business too much. So while we were hitting amazing numbers and we were achieving amazing things and the team was in place to some degree, we hadn’t built certain things out in a way that truly would’ve taken us to the next levels from there. 

So in the end, that business was best packaged with a bow on it and ready for another company to take over that already had infrastructure things built out that we should have, that we would’ve, that we could have, but we decided that that juice wasn’t worth our squeeze and that somebody else was better suited for that and that we could get a premium in the marketplace so it was better to sell that company. 

The second thing that I’m most proud of in entrepreneurship and in this journey that we’ve been on as a company and as a group is hitting that same level but differently. Hitting that level where things are clicking, good money’s coming in the door, there’s a ton of growth, and we’re doing amazing, but doing it while you have the team in place and to have built the systems correctly hits completely different. 

It is a completely different level to be hitting big numbers and crushing it, but doing it the right way where people can still have lives and relationships and families and you’re not relying on hundred-hour work weeks, but still hitting that level of success and growth because growth is still extremely important even if you’re hitting good numbers. 

Now, doing what with Saint sustainably and strategically and knowing what we need to put in place at each step, right? Because entrepreneurship’s a journey and sometimes reaching success also has equal amounts of problems that you didn’t foresee. But when you have the experience, you can move around those and build around those at those stages. 

It’s been a blessing to be able to build an infrastructure that can grow to the moon in a marketplace and create a great work environment and an amazing happy staff and team at the same time. That’s definitely been the biggest blessing in my career. To build a company correctly, you must think in decades and you must strategize and framework accordingly. Whether it’s staff systems or sales, you must be able to visualize the whole and that’s where people with experience have the leg up is that they know what it’s supposed to look like and how it will be at scale. 

What is the biggest challenge you’ve handled so far in your career, and what is the outcome?

Anytime I think about challenges in entrepreneurship and business, from my experience, it surprisingly is never the actual business. It’s only two things. It’s people’s problems that are ongoing because the bigger your staff gets, people problems seem to multiply with the way that people come together and work together, especially in fast paced or high stress environments, whether there’s projects or things that raise the temperature. The other biggest challenge that people will continually run into if they don’t plan accordingly is the market. 

The market’s bigger than any individual skill set and it’s even bigger than any individual company. If you were fighting the market plan to lose, I had to learn this the hard way. With people, what’s nice is that it’s your fault. Even though that’s bad news you might have made some bad people decisions or some bad hiring or maybe you didn’t and something changed in that individual that made them not a good fit for the organization at that time. 

The good news is you can actually change that. So if you’re in a leadership position in a company, whether that’s as an entrepreneur, as a C level executive, as a manager etc, you have the ability to improve that in your own hands. You can do that and the number one fix for the people problem that we’ve always dealt with is to make sure that the staff that you have today, whether that’s somebody in a leadership position that you’re evaluating or somebody as a frontline employee, all top to bottom, you must candidly evaluate if they’re a good fit today and also if they look to be a good fit in the future, if there’s growth there, if they’re a growth-minded person that will go with the company through the various phases. 

One of the biggest issues you’ll see with hiring consistently is you take an amazing employee in one role and you go, Well, they’re an all-star so we should bump them up and then you bump them to a manager position that’s above where they were at because every company likes to hire internally. It’s always the preference, right? But when you bump them up to a new level and they start stumbling and they start falling, you can never undo that. If they’ve stepped into a higher level position and they’re failing at that position, whatever it is, if they’re not making it work and they’re not a good fit, it’s heartbreaking cuz they were so great right here, right? and then you try to give them that next step up. 

But not everybody’s ready for that and not everybody has the skill set. So as an employer, your job is to give them additional training if they need it, but also know when to cut ties for the good of the bigger organization. We had to do that at our previous company multiple times. 

It was always heartbreaking, but it was for the best of the team and those were tough decisions that were the right decision. The takeaway to keep in mind here is that you can’t go back once you’ve bumped somebody up. There is typically no successful demoting somebody and having them just be completely okay and full morale and not having them spread that negativity to other team members, which is really the worst-case scenario. 

You’re almost always better off removing and replacing them with somebody that can fill that role, even if it’s outside the organization, which sucks. When you’re dealing with market issues, which are trends that are much bigger than you or dynamics that are much bigger than your company, the solution is you must find what specifically you are being limited by in the market. Are you being limited by revenue where there’s just not enough to go around? 

Are you being limited by a ceiling where the complications get so big that you can’t go beyond a certain ceiling? That does happen in certain industries with certain business models. For us, what we learned was that we hit a ceiling hard. When we bumped into that ceiling, we thought the solution was to add additional companies so that they could all hit that ceiling, but the gross revenue would be higher because each company would be successful. 

Instead what we found was that the market dynamics were actually slowly lowering that ceiling. The ceiling was crushing all of the companies and we thankfully got out ahead of it. But what we learned and what the big takeaway was, was that it didn’t matter if we were the best operators in the world, the ceiling of that industry with really robust compliance constraints, with really massive changes ongoing in that space and competition piling into the industry. 

Between those three things alone, it really started to thin margins very quickly. What we realized was the future road was not going to be better than the past, and that was the moment we said, time to pivot, and sell the company to somebody that wants to take that journey, and will move to a market that is better suited for our skills. Our team does not have a ceiling.  Where we’re at today, we chose real estate because we had that background and we had that experience and we know that we can deliver a better experience to the investor than anybody else that’s competing in our niche of income funds in the real estate space. 

So if you’re gonna choose a new industry and you’re in that evaluation phase, you wanna find a niche that you can own and be the absolute best in that has no ceiling. So you own a sliver, but that silver has no ceiling and can go to the moon completely and if you know that, then you’re in a good place for your industry. 

In the end, you need to niche down and go big. Those are absolutely the most important things when choosing a market. 

What are your responsibilities in your current role?

The number one search that you can ever make in your career is to find a role and a position that matches your skillset naturally. So if you have a natural skill set for something you want, find a job where you can combine those two and absolutely flourish. In my experience, on an entrepreneurial journey, I’ve had to wear a lot of hats just like everyone when starting companies. But the best thing about today is that I can sit where I’m most suited and that is to growth. I am the number one chief, 100% responsible party in our company and for taking Saint to the next level, I always feel most comfortable getting the responsibility to grow and slay the dragons and push things forward. Now there are things I’m not as well suited to that I get pulled into at times, but the answer to the question of how you work through things when you’re not well suited to them is not how it’s who. 

So you need to find the who to solve that problem if you are not well suited for the how and if you think of those terms and you’re looking for the best person to do this, literally in modern business, you can go online and in a five-minute search, find somebody that’s an expert in the craziest niches that anything you don’t want to do, there’s somebody that’s a level 9,000 at that skill. So find the people that are good at what you’re not. When you’re in a founder role of a company, especially a small to mid-size business that’s already gotten through the startup phase, there’s this amazing ability as a founder that you have to put yourself into a role that’s high leverage for the business where you’re also best suited. 

The issue is if you’re not careful, you end up getting away from your strengths and moving into a little bit of everything and being like a jack of all trades leader, which is actually extremely dangerous at later stages past the startup phase. 

That said, the business has to be managed and you still have to be close to the performance. So how do you do both? How do you not get involved in tasking and micromanaging and be over-involved in certain things that you’re not suited to while still being so close to the numbers and the business and the operations and the systems that manage success? 

The answer is managing KPIs and key performance indicators, and it’s in each piece of the business. You must know what the most important metrics are that you need to keep an eye on to define success. Because if you define success, whether that’s a growth rate of a certain KPI or it’s an expense ratio or some other calculation, that’s how you look at the entire business quickly to understand where different pieces are at that exact moment, what needs more attention, and also what’s performing at the highest level, what the all-stars of that company are doing. Early on in startup mode when there are only several people. 

What type of work environment do you drive most?

Well-managed KPIs are the single biggest differentiator between successful businesses and businesses that have lost their direction and don’t have a clear, efficient path to where they’re trying to get. The truth is, I love what I do every day because I chose it the first time around starting a large-scale business. Every single day I get to work on investing full time. Investing is a weird career because, at the end of the day, it’s something that evolves over time. This is the perfect environment for my personality because it’s something new every single day. We get to go after huge deals, evaluate big things, and be close to the major transactions while they are happening. 

Truthfully, even from the start of business, my mind was always set on working on the biggest and the best things. So every deal and everything that we focus on and every discussion and every negotiation, it feels heavy, it feels significant and with the team we have in place, it’s exciting because I know we’re gonna deliver on it and that’s what I love most about what I do on a daily basis. 

Company culture is something that sets apart the businesses that are put together without forethought, but without a predesigned plan and then the businesses that know exactly what they need to do and the type of people they need to bring in for key roles in order to perform at the highest levels and achieve something really truly amazing and unique. That team of A team players the top talent that want level 10 opportunity and in a position where you’re going after that level 10 opportunity, that is the work environment where A players want to be and that’s the work environment I want to be surrounded with because the air is very thin when somebody’s operating at an extremely high level and it’s often lonely when they’re the only person in an organization and they want to go to the top and other people around them are not interested in that. 

So, that person needs to be surrounded by other A players, but something magical happens if you put those A players together and everything multiplies and the production of those teams is much greater than the sum of their parts. But that team together can come up with X times a thousand. Being part of those moments where things are clicking in and an amazing group is creating something amazing is extremely unique in the business. That’s what I’m trying to be around all the time. When we as a company look for players, we’re looking for unique skill sets, we’re looking for somebody that wants to operate at the top, and we’re looking to put those people together because we know that not only does it boost all of their morale and all of their output, it also boosts management and leadership because everybody steps up when there’s new people and they’re doing amazing. The whole team gets better.

Frequently Asked Questions:

What are some key responsibilities of a founder?

Key responsibilities of a founder include setting the company’s vision and strategy, securing funding, hiring and managing a team, and ensuring the company’s success and growth.

How can a founder effectively manage their career and team?

To effectively manage their career and team, a founder should prioritize clear communication, foster a positive company culture, set realistic goals and expectations, delegate tasks and responsibilities, and provide ongoing feedback and support to team members.

What are some common challenges faced by founders in managing their career and team?

Common challenges faced by founders in managing their career and team include balancing competing priorities, dealing with uncertainty and risk, navigating interpersonal relationships and conflicts, and managing stress and burnout.

What are some strategies for overcoming these challenges and achieving success as a founder?

Strategies for overcoming challenges and achieving success as a founder include building a strong support network, staying focused on long-term goals, maintaining a positive mindset, seeking advice and mentorship from experienced founders, and investing in personal and professional development.