Adam Rubenstein: “Building a business has its ups and downs”

Work should be fun. When you spend 8+ hours each day working, there has to be an element of fun and excitement. I tell people I work with that, while every day isn’t going to be a joyous walk in the park, we should all look forward to going to work. Look forward to seeing […]

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Work should be fun. When you spend 8+ hours each day working, there has to be an element of fun and excitement. I tell people I work with that, while every day isn’t going to be a joyous walk in the park, we should all look forward to going to work. Look forward to seeing our colleagues who have become our friends. And that if the day arrives when you wake up and despair of having to go to work, you probably need to look for a change. I believe that by creating an environment that allows for personal and organizational growth and opportunity, as well as having fun, we’ve created something special.

As part of my series about the leadership lessons of accomplished business leaders, I had the pleasure of interviewing Adam Rubenstein.

Adam Rubenstein is a serial entrepreneur who has built 3 successful companies. In his current role as CEO and Co-Founder of Traq365, he oversees Sales, Operations, and Legal. He most recently served as the Co-Founder & COO of MotionPoint Corporation. Mr. Rubenstein ran the sales organization, building MotionPoint from 0 dollars to 40+ dollars million annual revenue, with ARR of more than 18 million dollars from 1,200 top-tier customers. Adam holds 19 patents for technologies associated with proxy-based website translation.

Prior to MotionPoint, Mr. Rubenstein co-founded Convenience Products Corporation (“CPC”) to create a market for new technology-based products — prepaid calling cards and prepaid wireless. He conceived and implemented many of the merchandising, marketing, and technical innovations brought to retailers by the prepaid card industry. Convenience Products was purchased by ConQuest Telecommunications.

Mr. Rubenstein’s broad expertise includes conceptualizing and building cost-effective, scalable, rapid production and delivery processes for data management. He holds a bachelor’s degree from The Colorado College and an MBA from The Wharton School of Business.

Thank you so much for joining us! Can you tell us a story about what brought you to this specific career path?

There’s a saying…”Nothing happens until you sell something” and I vigorously believe this is correct. No matter what you build nor how good the product or service is, ultimately you have to sell it to someone. So sales is at the core of every business. Over my career I decided that while sales as a science was in its infancy I was going to become an expert in sales and sales management and try to bring a scientific approach and more rigorous methodology to sales.

Can you tell us a story about the hard times that you faced when you first started your journey?

Just as Moore’s law says that computer chips will double in power every 12 months, Adam’s law says that when building a company, everything will take 3 times longer than planned and cost 3 times more than expected.

We were building one of my prior companies and from a funding perspective, we were on our deathbed. One of my founding partners said “what are you going to do? Wait for the sheriff to throw you out?” as he boxed his personal stuff and walked out the door. We — my other partner and I — never gave it a moment’s thought. We had our family and friends’ investment and we were going to go down swinging.

Later that week my partner flew to the midwest for a Friday sales meeting. He flew home on Sunday — remember it was way cheaper to fly over a Saturday night — with an order for a 250 store installation. It literally saved the company. We eventually sold that company to a larger competitor for millions of dollars. Our investors made a 10X return.

The partner that left? He gladly traded his shares for the travel expenses owed to him; he couldn’t imagine the company would succeed without him.

Where did you get the drive to continue even though things were so hard?

I’ve always been a fan of Winston Churchill and my favorite Churchill quote is “When you’re walking through Hell, just keep walking.” During difficult times, I follow this aphorism religiously. I break down the challenge I’m facing into manageable steps and then I push myself forward.

I used to think life and business would get easier but neither does. Success is, as Thomas Edison said, 1% inspiration and 99% perspiration. I push myself forward with what I feel is like grim determination. One foot in front of the other, day in and day out until I complete the task, project or business. Success is always ahead; you just have to keep going far enough to find it.

So, how are things going today? How did grit and resilience lead to your eventual success?

Things are going well because I feel strongly that we’re building something that is going to have a huge impact on salespeople and sales management. We’re working in a nascent industry and I’m confident that it’s going to be a big opportunity.

From personal experience I know where the most frustrating challenges can be found in sales. First, it’s always hard to hire great sales people because the one thing they always sell really well is themselves. And secondly, no matter how talented they are when hired, they always need continuous coaching because the world, the technology and the competition continue to evolve.

There are so many tools available that sales teams bolt unto their sales tech stack. Maybe a thousand new products in the past 10 years. But, with all the new technology, so few have the impact we all hope for. It’s our plan that Traq365 will change the game dramatically. We’re going to make sales people more effective.

Building a business has its ups and downs. I fought with our value proposition, making sure that my vision and our reality were closely meshed. There are days of frustration and brief moments of excitement as we move forward, building something that will achieve the improvement in sales that I know is so critical and necessary.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

Most of the stories I can recall are more terrifying than funny. I do remember a time almost 20 years ago that we were trying to calculate the number of unique words on the website. This was before we developed the tools to perform this analysis accurately.

Our approach was to print 1,000 random pages from their site and attach the the pages onto the walls of our office. We then assigned each wall to a different person and had them count the words on each page to get a rough estimate of the word count. Then we multiplied by the number of pages on the site.

We did get a number. But years later, when we won the business, and had better technology, we learned that our prior analysis was off. Way off! Thankfully we didn’t win that business based on our first analysis. The costs would have sunk us.

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

Our founders (me and my two partners) have a history of tackling big problems and Traq365 is tackling a really big problem. We’re using AI to mine sales conversations for the nuggets that can be used for both deal strategy and sales enablement.

We like to work backwards, starting with the solution and then seeing if we can develop an approach that will yield the solution. As salespeople and sales managers we know the environment we’re working in, we’ve built businesses from the ground up, we’ve solved really big problems in the past and now we’re doing it again. And failure is not an option. More importantly, we know what the value proposition looks like. It’s unacceptable to us if the tool doesn’t meet our vision because we intend to change the world of sales.

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

Entrepreneurs are a unique breed. It takes drive, vision, curiosity, empathy, and a large dose of risk taking. I added risk taking because that’s really the key ingredient. Yet I don’t look at what we’re doing as risk taking because I believe in our technology and I know that I can sell it. Maybe that’s the final ingredient. An almost unhealthy dose of optimism. It’s just know that we’re going to change the world because we are so intimately knowledgeable about the problem we’re solving and the cost of that problem.

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?

There’s no one person who has had that singular amount of impact … unless of course I mentioned my father. Rather, it’s a lot of people that I’ve worked with in the past, watched their performance and did my best to emulate them.

And there are those few people who I really valued, not because they explicitly taught me anything in particular, but rather because watching them, and analyzing their behavior and thinking made me a better person. There are a few people who are deep thinkers. They will tweak a problem in their heads like a rubik’s cube until they figure it out. And then there are several friends who are grinders. They’ll put hours and days into getting something done when everyone would have quit. And I know a few creative types who start from a place that I would have never considered and re-define the problem uniquely so that a solution is possible. I have absorbed all of these people into who I am.

How have you used your success to bring goodness to the world?

We spend so much of our time at work that I think the work environment should be really strong, really positive. I believe that there are 4 goals that leadership should bring to every company.

First, everyone in the organization should take pride in building a great business. Regardless of the position, we each have the opportunity to make a difference. I think of business as if it’s a person and we want to craft the perfect person.

Second, everyone should continuously strive to be better. Better at something. A better writer, speaker, technologist, or sales person. I don’t care what they choose, only that they must choose to evolve rather than stagnate.

Third, we’re all working because we need to take care of ourselves, our family and our business. Otherwise, without money, we can’t do many of the things that propel ourselves and the people around us forward. We can’t be embarrassed that we’re here to make money for ourselves and the company.

Finally, work should be fun. When you spend 8+ hours each day working, there has to be an element of fun and excitement. I tell people I work with that, while every day isn’t going to be a joyous walk in the park, we should all look forward to going to work. Look forward to seeing our colleagues who have become our friends. And that if the day arrives when you wake up and despair of having to go to work, you probably need to look for a change.

I believe that by creating an environment that allows for personal and organizational growth and opportunity, as well as having fun, we’ve created something special.

What are your “5 things I wish someone told me before I started leading my company” and why. Please share a story or example for each.

It’s not that I wish someone had told me 5 pieces of wisdom because, as an entrepreneur, I probably would not have listened anyway, certainly not when I was younger. That’s why I’m an entrepreneur. Someone more thoughtful would listen and react but in so doing, would probably do the smart thing and quit. But entrepreneurs can’t quit. We just push on. That being said, there are at least 5 truisms that require more thought:

  1. Everything takes much longer than you plan and costs far more than you expect. Having done this multiple times, I now have a rule of “3”. Everything we do takes 3 times longer than planned and costs 3 times more than we expect.
  2. Building awareness online is way more difficult than the pundits say. We hear about the instant successes because they’re fun to read about but the reality is building success online takes time and hard work. There’s no shortcut.
  3. Raising money is hard even when you’ve had several past successes. People are reluctant to part with their money. They are risk averse and the number of failures they witness far exceeds the successes. Even with my strong track record, a friend once said to me when I was looking for funding, “I can’t see lightning striking you again.” He didn’t invest.
  4. Logic plays a very small part in how people make decisions. We build our solutions by applying logic to a problem. But buyers are so often influenced by their emotions and past behaviors. Which makes building and selling a new product or service chock full of unexpected challenges. From a past venture, when having difficulty selling, we used to say “Company X wouldn’t buy 10 dollar bills for 5 dollars.”
  5. There’s a lot to be said for working from home, but working from home on creative problems remains difficult. Creativity seems to come out of the bottle really easily when brainstorming in person but I’ve not had the same satisfaction when meeting online. Of course, maybe I’m doing something wrong or running my meetings incorrectly. Yet, online meetings are not the same; there feels like something missing; maybe it’s the physical energy each person brings to a meeting that doesn’t transfer well when online.
  6. Understand how your company will be valued before you start. Valuation models are fairly consistent from year to year. It’s important to understand how a VC or Private Equity is going to assign value so you have something to target. Some types of businesses get very high valuations while others get low valuations. Knowing where you fit in is one more aiming point as you build the business.

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. 🙂

I think that we do a disservice to our kids during their late education because we don’t address all the stuff they’re going to need once they leave home. We need classes on personal finance in high school. This should include banking, mortgages, the stock market, general economics and human behavior. So many people don’t have a solid foundation in these areas and they either let opportunity pass them by or make fundamental mistakes that could have been avoided.

How can our readers follow you on social media?

They can follow me on LinkedIn at:

They can follow Traq365 at the following:

This was very inspiring. Thank you so much for joining us!

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