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Sit Down with TechnologyAdvice CEO Rob Bellenfant

Jerome Knyszewski



This is a photo of Rob Bellenfant, CEO and founder of TechnologyAdvice

Rob Bellenfant started young. When he was six years old, he started his first business. Between the ages of six and twelve, he also started seven other enterprises. He even started his first tech business when he was twelve years old. So, you might say that Rob was born to be a successful tech CEO. And now, he is.

As CEO and founder of TechnologyAdvice, Rob Bellenfant has kept his business success going. The company currently has over 350 members, and it’s also growing at a rate of 40% every year. As a serial entrepreneur, Rob has founded dozens of ventures for the past twenty years. His competitive spirit also enabled him to find success at each of these ventures. He likes to push everyone he works with so that they can all achieve their goals.

What does TechnologyAdvice do? Rob Bellenfant has built the company for the purpose of “educating, advising, and connecting buyers and sellers of business technology.” Over the years, the company has become a trusted partner and resource for buyers who wish to grow their businesses, and for vendors who wish to expand their market. With Rob’s hard work, TechnologyAdvice was included in the Inc. 5000 list of Fastest-Growing Companies in America for four years in a row: 2014, 2015, 2016, and 2017.

Before starting TechnologyAdvice, Rob Bellenfant founded the Thrive Marketing Group, Thrive Creations, 615 Ventures, and Eat Well Nashville. Whenever he gets free time, Rob doesn’t stop working. He spends his leisure time investing in real estate and angel investing. Besides, Rob doesn’t stop learning, as well. He also spends his free time studying personal finance.

Throughout his long career, Rob Bellenfant has received the 2015 Nashville Emerging Leader Award, the 2015 UTK Alumni Promise Award, a 2019 Nashville NEXT Award, and a 2020 Nashville Business Journal 40 under 30 award.

Read more interviews with successful CEOs here.


Jerome Knyszewski: 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?

Rob Bellenfant: 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.

Jerome Knyszewski: 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?

Rob Bellenfant: 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.

Jerome Knyszewski: 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?

Rob Bellenfant: 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.

Jerome Knyszewski: 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.

Rob Bellenfant:

  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.

Jerome Knyszewski: 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?

Rob Bellenfant: 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.

Jerome Knyszewski: How can our readers further follow you online?

Rob Bellenfant: Reach out to me on LinkedIn or follow the TechnologyAdvice Demand Gen Insights page.

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


Jerome Knyszewski is the Reputation Management Expert with the most recommendations and endorsements on the professional network, LinkedIn. His specialties are Online Reputation Management & Marketing, Strategic Alliances, Business Growth Strategies, He is a best selling author and Professional Speaker.

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