Rob Bellenfant of TechnologyAdvice: How To Delegate Effectively and Be Completely Satisfied With the Results

An Interview With Jerome Knyszewski

Jerome Knyszewski
Authority Magazine


Resist the temptation to direct: Once you’ve handed over the task, resist the urge to check in on the specifics of the process. You’ve hired the right people, now let them work. If they come to you with questions, throw the question back to them. You’ll often be surprised that they will come up with an answer that is as good or better than what you would suggest.

As part of my series about the “How To Delegate Effectively and Be Completely Satisfied With the Results”, I had the pleasure of interviewing Rob Bellenfant, a serial entrepreneur and investor. He is the founder and CEO of TechnologyAdvice, and has created dozens of other businesses over the past twenty years. Rob has a competitive spirit and constantly pushes everyone he works with to achieve their goals. Rob calls Nashville, TN his home along with his lovely wife and four children. In his free time, Rob enjoys real estate investing, angel investing, traveling, learning about personal finance and spending time with family and friends.

Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

I never listened to adults when they said “Don’t talk to strangers,” so as a kid I was perfectly happy going door to door, selling arts and crafts, selling lemonade or cookies, and raising money for Scouts. When I was 8 years old, I saw that a lawn care company was charging $35 to mow lawns, and although I was too young to push a mower, I knew I could compete. I started Weed Pickers Plus, which was my first business. I pulled weeds and planted flowers for 3 clients: my parents, our neighbors, and a family friend.

Then at age 12, I started cold calling businesses with two of my friends and designing brochure websites for them on Microsoft Frontpage. That led to us investing in a server starting our own hosting business, so we could get some recurring revenue. In the process of learning how to secure and manage our servers, we learned a lot that we then turned around and started to offer as a hosting management service, when I was 15 years old. Our freshman year of college, my business partner bought out my stake in the company, and I started buying companies on eBay.

Ad-Site Advertising — which eventually turned into Thrive Marketing and then into TechnologyAdvice — is the only one of those businesses that survived.

Can you tell us a story about the hard times that you faced when you first started your journey? Did you ever consider giving up? Where did you get the drive to continue even though things were so hard?

Six weeks after purchasing the Ad-Site Advertising business — which brokered web ads for customers — the only supplier of ad space we had for all of our clients went out of business. I thought that maybe I had bought a fifth company off of eBay that was going to fail. But after settling with the seller and looking at the assets I had leftover, I realized I had a good customer list I could work from. I started reaching out to those clients directly to see how I could help them, and eventually we were able to start brokering ad space for them.

The drive to succeed and continue through the adversity sounds so heroic when you put it like that. At the time I wanted to salvage this business deal and recoup my investment. I also enjoyed the challenge of finding ways we could help these clients.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lessons or ‘takeaways’ you learned from that?

I have always loved running a bunch of different ventures at once: I bought 5 businesses off of eBay! After buying Ad-Site Advertising from a serial con man — he went on to repeat the scam he pulled on me over 10 times — I learned to complete my due diligence before purchasing a company. I also love the opportunity and promise of starting something new, but there’s no way to fully build a business from nothing without help. Those first few years in a new business really take a lot of concentration and hard work to guide policy and ensure that you have the right people in the right places of leadership to take everyday operations out of your hands later.

What do you think makes your company stand out? Can you share a story?

TechnologyAdvice has had its ups and downs but we’ve been able to learn from them and grow. Back in 2015, we had this great idea for a way to further productize our data in a new way. We spent months of work from resources all over the company and launched a new product — to crickets. Turns out, no one wanted or needed our product. We had grown our employee count considerably in anticipation of this product, too. It was disappointing to let go of that dream and even more disappointing to let go of many of the people who worked on it.

Ultimately, that lesson made us stronger. We concentrated our efforts back on our core product offering and grew that business significantly over the next few years. That focus and growth made it possible for us to acquire nearly 40 new web properties this year and expand our offerings in a thoughtful and strategic way.

Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?

Take time out to work on the things outside of your work and your job. I find that when I have a real problem with the business that I’m wrestling with, if I give my brain a little break by playing with my kids or working out or doing something creative, I often stumble across something that clarifies my thinking or gives me a breakthrough on a problem. My employees joke that my hobby is business, which may or may not be true. But I make time for myself and my family, which really keeps me grounded.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

Back in high school, the librarians used to send me to the principal’s office all the time because I used the library computers to run my IT business during school hours. She didn’t really understand my business, but when I asked if we could use an empty room near her office to run our business during lunch or study halls, she agreed. It kept me out of her office and in a room where administrators could keep an eye on me, and reduced the amount of paperwork she had to do. She didn’t have to help us. She could have punished me, instead. But she didn’t, and I’m grateful. She’s still a principal, and I go back and see her sometimes.

Ok thank you for all that. Now let’s shift to the main focus of this interview. Delegating effectively is a challenge for many leaders. Let’s put first things first. Can you help articulate to our readers a few reasons why delegating is such an important skill for a leader or a business owner to develop?

When you start delegating tasks to other individuals, you not only gain yourself a break, you also open your days up to do the big-picture work that can jumpstart growth. Some people have drawn the distinction between working on the business vs. working in the business, and I really like that view. When you work in the business, you perform all the daily tasks that keep the business running. But leaders that work on the business take the time to strategize, improve processes, and identify areas for growth.

You don’t want to be so indispensable to your business that you can’t take a day off when you’re sick or leave the shop to go on vacation. The best managers teach their employees to run the business for the sake of the company’s longevity and to empower their employees to hold ownership over the processes. These managers find that their employees care more about their work, work harder, and invest themselves in the improvement of the company as a whole.

Can you help articulate a few of the reasons why delegating is such a challenge for so many people?

The Venn diagram of business leaders and people who subscribe to the notion that “if you want something done right, you should do it yourself” is often just a circle. We may have been the smartest person in the room for most of our lives, and that ego-boost is hard to let go of. The validation we get from being the guy with all the answers or the gal who knows how to fix everything can be addictive!

Also, it feels harder to take the time to teach someone else how to complete a task. Many of us would rather take the 10 minutes to complete the task ourselves instead of the hour it takes to teach it to someone else. Unfortunately, that means that every time the task needs doing, we’re the only doers available.

In your opinion, what pivots need to be made, either in perspective or in work habits, to help alleviate some of the challenges you mentioned?

If you love the validation that comes from knowing all the answers, it may help if you begin to watch your employees when they figure out a difficult task. You can delight in their sense of discovery and accomplishment and simultaneously delight in your own newfound free time.

If you need help investing the front-end time to teach employees complicated processes, consider instead the amount of time you’ll earn back each day by delegating the task. Take that task you spend an hour on every day: by investing two hours to teach an employee to take over the task, you can save yourself 240 hours over the course of the year. With all that time you could develop a new product line, focus more on your marketing plan, or take a vacation for six weeks!

Can you please share your “Five Things You Need To Know To Delegate Effectively and Be Completely Satisfied With the Results?” Please share a story or an example for each.

  1. Get the right people in the room: This rule goes for everything from hiring to planning. I make sure that we hire capable employees with growth mindsets that are curious and willing to take ownership of their jobs and their processes. Then, when we set out to create new products or improve our systems, we get the right stakeholders together. This helps us ensure that all parts of the business have a say in the outcome.
  2. Be specific about outcomes: Whether you use SMART goals or another outline, you’ll want to make sure that you define what you want the product of the task to be, how the task contributes to the improvement of the business, and when the task is due. These items should be enough for your employees to get started.
  3. Be vague about process: Consider yourself a consultant on the process. If you define the outcomes of the task and leave your employees to figure out the process, you can save even more time and help your employees grow even more. Set two fifteen minute meetings. The first to define the outcome and the second a week later to discuss roadblocks and improvements. Many tasks don’t need a prescriptive process. And your employees may surprise you by discovering improvements and shortcuts that were in your blindspots before.
  4. Resist the temptation to direct: Once you’ve handed over the task, resist the urge to check in on the specifics of the process. You’ve hired the right people, now let them work. If they come to you with questions, throw the question back to them. You’ll often be surprised that they will come up with an answer that is as good or better than what you would suggest.
  5. It’s okay if their way is different than your way: Repeat this one to yourself over and over, if you have to. People often say “Focus on what you can control,” but to people who are used to controlling every step of every process, that phrase may feel like a free pass to micromanage. Instead, only focus on what you need to control. And rejoice in the freedom that comes with not needing to think about the rest.

One of the obstacles to proper delegating is the oft quoted cliche “If you want something done right do it yourself.” Is this saying true? Is it false? Is there a way to reconcile it with the importance of delegating?

If it weren’t true, it wouldn’t be a cliche. But that doesn’t mean it’s always true for all circumstances — or for all people. You didn’t get to be the boss because you did everything yourself, but because you’ve shown the capability to drive positive growth for the company.

Instead of that cliche, consider this from Crystal Mullins, our Chief of Staff: If you’re not replaceable, you’re not promotable. Do you want to continue doing data entry for the rest of your life, or would you like to be the person who analyzes the data and directs the strategy? If you’re stuck copy-pasting rows of numbers all day, you can’t make the big decisions or think the big thoughts.

Thank you for all of that. We are nearly done. You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

In the context of this conversation, I would love to see more companies investing in educating their managers as coaches. We’ve found that it improves outcomes for individual contributors, helps us grow leaders from within the company, and ultimately it grows our business. While it can be an investment of time on the front-end, taking a coaching mindset can create a flywheel in your company.

How can our readers further follow you online?

Reach out to me on LinkedIn or follow the TechnologyAdvice Demand Gen Insights page

This was very inspiring. Thank you so much for the time you spent with this!

About the interviewer: Jerome Knyszewski (Kenchefski) is the CEO of HeavyShift. Jerome serves as an advisor to CEOs of Fortune 500 companies as well as entrepreneurs who disrupt their industries and therefore tend to be targets of malicious online attacks. His company builds, protects, and repairs the online presence & reputation of many celebrities, products and beloved brands.