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A Conversation with Brock Flagstad about Entrepreneurship and Leaving a Lasting Legacy

Brock Flagstad is an entrepreneur specializing in customer acquisition.  He has over 15 years of experiencing building, leading, and growing companies.  He is the CEO and Founder of Channel Clarity, a lead generation company.  He also owns Oxford Tax Partners, Oxford Media, and Oxford Insurance Partners.  He has been working in direct to consumer marketing […]

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happy family with tree kids walk at sunset tropical beach
happy family with tree kids walk at sunset tropical beach

Brock Flagstad is an entrepreneur specializing in customer acquisition.  He has over 15 years of experiencing building, leading, and growing companies.  He is the CEO and Founder of Channel Clarity, a lead generation company.  He also owns Oxford Tax Partners, Oxford Media, and Oxford Insurance Partners.  He has been working in direct to consumer marketing and financial services verticals for most of his career.  The backbone of his work through Channel Clarity, has been in lead generation and customer acquisition.  From a 30,000 feet perspective, when Channel Clarity was founded it was designed to be a lead generation company.  Channel Clarity would advertise on a nationwide basis, attempting to help other companies find customers.  Over time, as Channel Clarity gained success in marketing financial services, insurance, debt settlement and resolution products, Brock began starting those kinds of companies himself and owning the entire process from the front-end customer acquisition to back end servicing. 

In the last few years, what lifestyle, habit, or behavior change has had the biggest positive impact on your life?

We were living in downtown Chicago and I was working all hours of the day.  I have three small children.  As much as you want to say that you’re around, the life and the business and the city itself separated me from my family in a way that was unintended and unfortunate, so we made a decision to relocate our family to Sea Island, Georgia.  We live next to the beach now.  With that has come consistent family dinners and more time together and it has been great.  The quality time that we all get to share has been fantastic.

The companies are all still based in Chicago.  Pre-COVID, we were planning to go back to Chicago every now and again to check in on things.  I had a desire to go back every other week or so.  It’s interesting, when we moved down here, the company had to really devise what our remote work would look like, and fortunately, we did all that work roughly nine months in advance of COVID hitting, so we were really well positioned to have our workforce operate in a decentralized way.  We got lucky for sure. 

When you feel unfocused, what do you do?

I exercise.  I play tennis everyday.  I hate the idea of running on a treadmill, but I love playing tennis.  It is so much easier to get your steps in when you enjoy your exercise. 

One of the other benefits of having endured this change in work habits is you realize you can’t force anything.  If you are unfocused and you are unprepared to execute the task at hand, walk away.  What is the quality of your work going to be if you’re not engaged and unable to focus?  Go exercise.  Take a walk outside.  Do something.  Get away from it for a bit and then hopefully you can return to whatever task that you do need to execute on with a clearer frame of mind. 

What advice would you give a smart and ambitious recent college graduate? What advice should they ignore?

It is so hard to do work that you don’t enjoy doing.  I have a friend that is an accountant, and he hates accounting.  I can’t imagine what his everyday is like, doom, gloom, and dread.  It’s unfortunate.  You’ve got to put yourself in a position to be able to do something you love and avoid doing things that you don’t really enjoy.  Some of that can mean keeping some work for yourself to do and some work you delegate or outsource to others.  Do something you love and follow your passion!

I firmly believe that you “don’t know what you don’t know.”  But even when you are unsure, you will know really quick what you don’t like doing.  If your work doesn’t meet the “whistle while you work” test, you’re doing the wrong thing.

If you are moving down a path of starting a business and you are trying to follow your passion, go get some experience in the workplace.  It is work, and you have to make sure you are rewarded for it.  Some people are financially motivated, some feel the reward in doing good work or the impact on their community.  It has to be worth your time. 

There is enough stress everyday with the challenges you face in business, so make sure you are comfortable with the type of work that you’re doing and that it checks your moral and ethical requirements for you to be comfortable.  Do not put yourself in a position where you are going to feel like you are compromising some of your values. 

Everyone has their own philosophical framework.  What is bad advice for me might not be bad advice for you.  You should focus on what will give you joy in your work. 

What is one lifestyle trend that excites you?

With our remote work lessons of COVID, we now see that the expectation of a 9:00 to 5:00 workday is maybe a little inaccurate.  I think we’re trying to compartmentalize our time for work and our time for family and our time for exercise.  Everything gets split up into its own neat box at times.  Where the remote work challenge comes into play is how to balance your family obligations with your work obligations and personal obligations.  I think the workday now looks more like blocks of time that are more divisible across the 24-hour day.  I think the deconstruction of what the workday means, what it used to mean and now what it can mean, I think that is going to set some people up for opportunities to excel in their work on their own time independent of their teams. 

I wake up around 7:00 am and make sure that the family is up and at ‘em.  Because there isn’t a commute, I get a little bit of extra time to sleep in.  There is not the same type of pressure to get up and go and avoid traffic.  Let’s get up and have breakfast and get everyone else set up for success.  I have a home office now.  I’ll work for roughly an hour and a half.  I’ll go play tennis at 9:00 am every day.  I’ll play for an hour or an hour and a half.  I’ll come back, shower, change, and get back to work.  I’ll work for another two hours.  By that point, I’ve accomplished roughly 50% of my workday and it’s not even noon yet.  I have lunch.  I may run some errands.  I’ll check back in and work again.  Then I may go hit golf balls or go to the pool.  At the end of the day, I will check in again and work a bit more.  I can still monitor communication for the remainder of the team.  The day is laced with more activities and things that I enjoy and that keeps me centered. 

Who has been the biggest influence in your life and why?

Friends, Enemies, and Competitors.  Friends build you up and support you when you’re down (and maybe even out). Enemies keep you looking over your shoulder but serve to keep you moving forward.  Competitors force you to define and maintain laser focus on your objectives.

What’s one of the biggest life lessons you’ve learned?

Business is about people, whether it’s your employees or your customers.  As you focus on building a team, we need individuals with different backgrounds and perspectives.  You are trying to build a problem-solving team.  If you are building a team of problem solvers, you don’t want everyone to have the same shared view of the world.  You need some people with different perspectives to challenge ideas.  You need to recruit those people, train them to be part of your business in a more effective way, and then make sure you are giving people opportunities for advancement.  Individuals generally get very efficient at doing their jobs, so they need to be challenged.  It is good to continue to apply stress to their position in a good way to keep them engaged.  The everyday challenges of business have taught me these lessons, not any one experience. 

What do you think it is that makes you/someone successful?

What you may define as success does not necessarily mean success to me.  To be successful, you need the ability to recognize what your real motivators are, what your individual drivers are, that overall awareness to a certain extent.  I think there are a lot of people that are really happy grinding in the office all day, every day.  They feel like they have accomplished something, and that sense of accomplishment is their true happiness.  For others it might be their bank account balance, and others might have more of a philanthropic focus.  To define what makes you successful, you’ve got to understand what your own happiness is and then work to achieve what that is for you. 

For me, it is financial as well as spending more time with my family, doing cool things, having great experiences.  Financial success is not an endpoint unto itself.  Being able to move my family to live near the beach is a good example of how financial success is simply another tool in the toolkit that can enable even more, deeper experiences. 

How do you stay motivated?

I think I wake up every day ready to go.  I am a very self-motivated person. 

Some people say, “failure is not an option”, but I don’t look at it that way because failures are lessons.  Not giving up in the face of failure – because of failure – is a great motivational tool.

What legacy do you hope to leave behind?

Smart, competent, well rounded children are the legacy that I hope for. 

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