Stephen Gerard of TGaS Advisors: Second Chapters; How I Reinvented Myself In The Second Chapter Of My Life

Pirie Jones Grossman
Authority Magazine
Published in
18 min readMar 4, 2021


When you need help — just ask for it. Too many times I was either to shy or hesitant to push things and ask for help or I wanted to appear to be in a better position than I was. I do not ascribe to the saying “fake it until you make it” and believe people see through a fake. There are times where you need a helping hand … just ask (without sounding needy).

Many successful people reinvented themselves in a later period in their life. Jeff Bezos worked in Wall Street before he reinvented himself and started Amazon. Sara Blakely sold office supplies before she started Spanx. Dwayne “The Rock” Johnson was a WWE wrestler before he became a successful actor and filmmaker. Arnold Schwarzenegger went from a bodybuilder, to an actor to a Governor. McDonald’s founder Ray Croc was a milkshake-device salesman before starting the McDonalds franchise in his 50's.

How does one reinvent themselves? What hurdles have to be overcome to take life in a new direction? How do you overcome those challenges? How do you ignore the naysayers? How do you push through the paralyzing fear?

In this series called “Second Chapters; How I Reinvented Myself In The Second Chapter Of My Life “ we are interviewing successful people who reinvented themselves in a second chapter in life, to share their story and help empower others.

As a part of this interview series, I had the pleasure of interviewing Stephen E. Gerard.

Stephen E. Gerard (, an entrepreneur and the ForbesBooks author of Stuck in the Middle Seat, worked in the corporate world for nearly 20 years before launching his first business, TGaS Advisors, in 2004. TGaS Advisors became an Inc 500/5000 winner for five years in a row and is still a thriving business.

After spending 20 years with large Fortune 500 companies and then a few early internet start-ups, Stephen decided to become a mid-career entrepreneur at the age of 40. After being downsized by a small company he proceeded to embark on a two-decade long journey of start-ups and investments. His first start-up from scratch, TGaS Advisors ( has sold over a quarter of a billion dollars of high-end advisory services to the pharmaceutical and biotech companies and operates on an International scale. The company has been involved in buy/sell transactions in excess of $100M and has been named to the Inc 500/5000 a prestigious five times. Stephen is current owner, investor and advisor to a number of entrepreneurial businesses across the world, and travels extensively to help support and manage those businesses. Stephen is a recipient of additional company-level, leadership/CEO, and business awards, a holder of a US Patent, and a retired CPA. He has an MBA from Monmouth University where he currently serves on the Board of Trustees and a BS degree from Rider University. When he is not traveling, Stephen splits his time between New Jersey and California with his wife and grown family.

Thank you so much for doing this with us! Before we start, our readers would love to “get to know you” a bit better. Can you tell us a bit about your childhood backstory?

Classic middle-class upbringing in a large, close-knit Italian family in New Jersey. My Dad was a high school science teacher with a part time insurance business (his side hustle) and my Mom was a stay-at-home Mom. Did all the typical activities as a youth (sports, music, activities) and spent every summer at the Jersey Shore. Had a wonderful childhood and very stable, conservative upbringing. We were the Cleaver family (Leave it to Beaver reference) … but Italian.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“Never fear failure … fear regret”. I have always believed you have to try a lot of things and you should never be afraid of failing. In each failure or set back, you dust yourself off and keep advancing. Fail-forward is another mantra I live by.

How would your best friend describe you?

A good companion. The word companion comes from the Latin word companis … meaning “with bread”. I try to be a good companion to everyone who I encounter (if they deserve a good companion). A friend or family might also add in funny, adventurous, fair minded, and one-step-ahead.

You have been blessed with much success. In your opinion, what are the top three qualities that you possess that have helped you accomplish so much?

While I never fashioned myself the smartest person in the room, I always felt I had a few aces-up-my-sleeve that would help me succeed. My top few qualities are: Tireless (I will outwork you); Creative (always looking for better and more creative ways to do things); and Fearless (not much scares me … as long as I have my health and my family’s health) — bring it on. Lastly — my mind moves very fast and my mouth (articulate) can keep up. When you combine those qualities, I can compete with the smartest person in the room!

Let’s now shift to the main part of our discussion about ‘Second Chapters’. Can you tell our readers about your career experience before your Second Chapter?

Seventeen years of climbing the proverbial corporate ladder in some large, well respected global companies. Worked hard, got an MBA and a CPA, and climbed the corporate ladder between 1984 and 2000. Had I stayed-the-course in larger companies, I felt I could have had a ‘top-job’ and lived a very fun, stable and prosperous corporate life. But that was not for me. I caught the small company bug during the first phase of the internet coming of age (1998–2003) and did a few small company startups in 2000–2003. The last one ended up in my downsizing — being fired. After that 20-year run of working for companies …. I new it was time for Act II.

And how did you “reinvent yourself” in your Second Chapter?

The day I was fired in late 2003, I walked out onto the sidewalk with the proverbial box-of-stuff from my desk being cleared out, and decided at that moment I needed to chart my own course. I had been keeping a “drawer” full of business ideas up to that point, but was not brave enough to go for it. Now, after being fired and being with 3 companies in 3 years, I decided now was the time (or never). The reinvention came from a sort of forced bravery from being fired but also having some financial means to give starting my own business a “go” in 2004. The reinvention was no-more-excuses.

Can you tell us about the specific trigger that made you decide that you were going to “take the plunge” and make your huge transition?

See above. I was tired of not totally controlling my own destiny and also of ‘blaming’ others for the way they ran things …. so it was put-up-or-shut-up time for me. Also — I could not bare the idea of going on more interviews and trying to explain 3 different jobs in 3 years, when I had 3 different jobs in 17 years prior to that.

What did you do to discover that you had a new skillset inside of you that you haven’t been maximizing? How did you find that and how did you ultimately overcome the barriers to help manifest those powers?

I had put in my 10,000-hours.

I was always entrepreneurial minded — even when I was in larger companies. That said, I was fortunate in that I had done many roles in business that lent themselves to starting my own business. It was almost that I had trained to be an entrepreneur without really looking at it as ‘training’. Having had roles in accounting, financial planning and analysis, manufacturing, then sales and marketing, and finally running a small division and group — I was “ready” to go out on my own.

I have also told others to sort of do what I did: LEARN in your 20’s … LEAD in your 30’s … and then LEVERAGE both of those in your 40’s to start your own business. That is really a summary of the path I was fortunate to take.

How are things going with this new initiative?

Between 2004 when I first launched the business, and today, we grew the company rapidly, sold it in 201 to a larger company, bought it back in 2014 and sold it again in 2018 … and I am still an investor today. Amazing journey with some amazing and hardworking people. The true entrepreneurial dream. Those business results and learnings have led me to be an investor and owner in a number of other global businesses and allowed me to have my family join me in those businesses. Just about every day I get to do “what” I want … “when” I want to, for “as long” as I want to. That’s satisfying.

Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

I cite a number of people in my book (Stuck in the Middle Seat) and would be doing about a dozen or so folks a disservice by singling one out. A few offered me heartfelt encouragement when I was thinking about venturing out on my own, and a few more actually helped me start and succeed. All of those folks are acknowledged in the book.

Can you share the most interesting story that happened to you since you started in this new direction?

I’ll share a funny story from early in my first startup (at least it was funny to me).

If anyone wants to look up the date to verify the weather, I was in Connecticut on January 15, 2004. It was three weeks into me starting a business and the day before my forty-first birthday. It snowed four inches that morning, and was 0°F in Connecticut on that evening with a wind chill that made it feel

like -20°F. The news on my car radio said it was “the coldest night in a century,” and I believed it!

I had traveled to New Jersey, then New York, and then lower Connecticut, from my home in Pennsylvania, for four distinct meetings on that day. I wanted to use my travel time as effectively as possible, so I stacked up a bunch of meetings. I boogied from meeting to meeting in the snow and the cold, and unfortunately, none of them bore any immediate fruit (sales). Read on …

The first meeting was with a printing vendor that I had given a lot of business to (hundreds of thousands of dollars) when I was at a large pharmaceutical company. During that time, he was very early on in his business, so I was helping a fledgling entrepreneur in a big way. I felt he would be a great help to me, and I offered to do some consulting work for him to grow his business and also help me get started. I also felt he “owed” me some help, aside from the fact I thought I could provide him some good advice. Well, he did not see it that way and, in fact, asked me to help him get more business with some free referrals? I was therefor what I thought was a well-deserved favor, and it turns out he asked me for a favor! That was the first confounding and sort of embarrassing meeting for the day. I was 0 for 1.

At the second meeting, I was pitching a paltry $7,500 consulting agreement with a company I had done some free advising for. I also thought they owed me a few shekels and a favor, but the person I was meeting with did not seem to see it that way. Not only was she not biting on the small consulting deal I was sort of pleading for, but she actually continued to seek free advice. It was another dose of embarrassment and head-scratching for me. I was 0 for 2.

For the third meeting, I sped my car into New York City for a meeting in Manhattan with a potential pharmaceutical client. That meeting was abbreviated from a planned one hour to twenty minutes and did not bear any fruit. After all the tolls and parking fees, I hustled back across the George Washington Bridge to make my way to Connecticut. So, by the time I was getting to the fourth meeting, we can see my day was not going well at all. I was 0 for 3.

The fourth meeting of my arctic sojourn was a 7:00 pm dinner meeting. I was having dinner that evening with an old colleague who was now with a top 20 pharmaceutical company. I really wanted to get them as a client. We had known each other ten-plus years and had done a decent amount of business with each other. We had a history and also enjoyed each other’s company. He had ventured out on his own in Europe, and I tried on a few occasions to help him and even tried to hire him. So, this was dinner with a fellow I also felt owed me some help … and maybe even a sale!

Let’s be polite and say the dinner went just OK. I was not feeling any energy or love from the meeting or the imminent chances for follow-ups. In fairness to him, he had just started with his new employer, and he needed to get his feet under his desk for a few months before recommending me. Fair enough, but waiting months for a recommendation was not what I was hoping for. Dinner sort of ended in a “meh!” I was 0 for 4.

So, after driving three or four hours to get to New Jersey, New York, and Connecticut for what turned out to be a few marginal (crappy) meetings, I was feeling a little down. I clearly felt I was owed more consideration than maybe I had earned, and that had me bummed.

After the dinner and a very long day, I went out to my car in the frigid cold and drove to my motel. I emphasize motel because it was a $55-a-night place where the heater is under the window, the room doors open to the outside parking lot (not a hallway), and you get one towel with a bar of soap the size of a thin mint. That’s all I could afford.

That’s where a little of the embarrassment and self-pity crept in. Months before this, I was a well-paid senior vice president of a company, staying in the nicest hotels, being driven to sales calls by my sales team, and eating at some pretty nice restaurants. I had a corner office in Princeton, New Jersey, in a beautiful new office building and had sixty people working in my group. I was on top of the world.

Now I was an entrepreneurial slug, in the hinterlands of Connecticut, well off the highways and byways, in the freezing cold … staying in motels. If embarrassment and pity were starting to creep in, they were about to come crashing down — literally. When I got out of my car to go into my motel room, I slipped on some ice by the trunk of my car and landed flat on my back. I had literally taken a header at 10:00 p.m. in the middle of a parking lot, on a sheet of ice, and I lay there like a turtle on his back.

I lay there stunned that I was lying on ice, on the ground, in -20°F weather. While I was not injured at all, I lay on the ground, eventually laughing at my predicament. My gallows humor kicked in. Oh, how the mighty had fallen (literally), and wasn’t it funny? I was on my back in parking lot of a $55-a-night motel on the coldest day of the century, the day before my birthday. I was literally alone, embarrassed, and pitiful! Another person saw me and, after asking if I was OK, said, “It’s tough being out on the road in sales, huh?” Now my plight was being parodied with Death of a Salesman humor.

As one final kick in the butt, and to add insult to injury, I could not get my motel room’s heater (a window unit covered in black soot) to get the room’s temperature above 55°F. It was a long day of crappy sales meetings, followed by an unactionable dinner, punctuated by an episode of Ice Capades in the parking lot, and a cold, uncomfortable night in the room.

If that does not bring a sense of embarrassment and pity to your soul, what will?

Did you ever struggle with believing in yourself? If so, how did you overcome that limiting belief about yourself? Can you share a story or example?

Confidence is built on the foundation of failure(s).

Early on in one of my businesses, I was going after Procter & Gamble’s pharmaceutical division. We really needed them to join in the benchmarking we were just beginning to do. I was able to get the name of the right buyer at P&G (or at least recommender), and I set out a plan to go after him. I sent a number of emails and letters/packets in street mail designed to attract him to speak with me on the phone. I was moving fast, and it was in the early days of trying to get a lot of sales calls in every day. I did not even think of flying out to Cincinnati from my Philadelphia base (first mistake).

I finally got his interest and had a conference call with him to review the benchmarking idea. After presenting the idea and service for my business over the phone, I thought the meeting went well. Not being in the room with a prospective client is never ideal because you cannot read body language, interest, and objections and get a feel for the meeting. But, heck, I was just starting out and moving fast (failing forward) and not wanting to spend the money to fly to Cincinnati. It’s also worth noting there were no other pharmaceutical companies within 250 miles of Cincinnati, so I could not make a run out there and meet with a bunch of prospects. At that time, I also was enamored with my long prospect list and did not think I needed the effort to go full tilt after P&G (and, boy, was I wrong).

Two hours after the sales phone call, I got an email that read: “We are NOT going to move forward at this time — but thanks.” Ouch! By operating under the fail-forward pirate flag, I had failed … but there was no “forward.” Maybe my mantra was wrong!

Well, I let the dust and disappointment settle and decided to follow up and ask why they decided to not move forward. P&G was nice enough to give me some feedback. The feedback made it clear to me that I did not describe the idea well enough to them and that I had blown it! They had said no for what I thought were the wrong reasons. How could I take this failure and move it forward?

I thought about options and decided I needed to see them face to face. I told them that I was going to be in the area, which was a white lie given I had no need to be in Cincinnati Ohio, and asked if they would let me stop in when I was there. They said yes to meeting with me again, so I booked my flight to be “in the area.”

I went back in, in person, and met with the same two people I had the phone call with weeks before. For that meeting I was also able to directly address some of the objections they had. I also left time to listen to their thoughts and needs and read the room for good and bad signals. I thought the second sales meeting went well, and they said they would give it another look.


A few hours later, upon returning on the one-hour flight from Cincinnati to Philadelphia, as I walked through the airport, I listened to a voice mail from P&G giving me the yes and the go-ahead! In failure, we had found a way to move forward and had done it pretty quickly. To this day, I can tell you exactly where I was standing in the vast Philadelphia airport and the elation I experienced. In retrospect, it is probably the most significant win I have ever had as an entrepreneur.

In my own work I usually encourage my clients to ask for support before they embark on something new. How did you create your support system before you moved to your new chapter?

I was fortunate to have a pretty large network of friends and colleagues who I was able to speak with for advice. I always tried to bring them some value in our discussions so it was not just me “taking” advice and was always available to help them. Since I did not start the business until I was working ~ 20 years, those colleagues had also risen to higher levels in a lot of organizations, so their help occasionally included introductions for business and sales, or they in fact contracted with me themselves. I’d like to think a friendly and generous nature afforded me those colleagues and their help during my career.

Starting a new chapter usually means getting out of your comfort zone, how did you do that? Can you share a story or example of that?

Closing a Sale Can Be Uncomfortable and is hard for me to do when it is a colleague or a friend.

During the Lunching Stage, which for me was roughly twenty meetings and a few months, I thought I was getting a lot of positive buying signals from prospects. As I stated, these were happy times because you are doing presales calls and learning about the offering and market needs, and not yet asking for a sale. All was good — or so I thought.

In particular, there were three prospects I had met with in the Lunching Stage that I was being ignored by in the Selling and Closing Stages. So, I had to push! Some of that push was uncomfortable because it was with friends and former colleagues. I eventually settled on the action of sending them a challenging email that broached a now-or-never tone. It was uncomfortable to do that, and even though the email was friendly, it carried with it a let’s-move-or-not tone to it.

I ended the email with a “signing off” from bothering them anymore tone, which was sort of a way of trying to turn the tables into them either pursuing me or telling me it was a no-sale. Either way, or as uncomfortable as it was, it was time to get a resolution. Ironically, and thankfully, all three of them emailed me back in thirty minutes and gave me real, tangible next steps.

The lesson learned: Don’t be afraid to push a little. People know you are selling something and trying to survive. If you are professional and have earned the right to ask for the business, go for it. Remember, you can only eat what you kill.

Fantastic. Here is the main question of our interview. What are your “5 things I wish someone told me before I started leading my organization” and why? Please share a story or example for each.

  1. When you need help — just ask for it. Too many times I was either to shy or hesitant to push things and ask for help or I wanted to appear to be in a better position than I was. I do not ascribe to the saying “fake it until you make it” and believe people see through a fake. There are times where you need a helping hand … just ask (without sounding needy).
  2. Never send an unsolicited proposal — make sure a potential client ASKS for a proposal. Too often when a good sales meeting is coming to an end, it is easy to say “I’ll follow-up with a proposal”. When you do this and a sales prospect did not ask for it, it becomes an easy way for them to end the meeting. You end the meeting hoping you made a sale, and they end the meeting — period — whether they wanted the proposal or not.
  3. Spend an appropriate amount of money and time on good legal advice and support for your contracts, confidentiality agreements, employment agreements, and anything else that should be in writing. Now a days it is pretty easy to get your hands-on good templates or get decent legal advice for a fair price. This is money well spent.
  4. Don’t waste time on partnerships or strategic alliances. Get out and sell your product and service … Once you are rolling, the real opportunities for other alliances will appear. In the beginning take full ownership of your success and do not rely on others. HOPE is not a strategy or the road to success.
  5. Time is your most precious resource so spend it wisely. You will need to pour endless hours into your business while your time, attention and energy are limited … not limitless. Learn where and when to focus, when to multitask, when to be fully present … and when to say no.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be?

Start a business doing what you love — even if it starts as a side-hustle for nominal revenue. If you stay at it, it can become something more meaningful or have a nice place in your life when you decide to retire, or can retire, from your full-time position. Now a day’s people are working well into their 70’s and beyond … why not be doing something you love for a fair return (money) that you totally control.

Example — If you are an Accountant in a firm in the middle of your career — entertain taking a few side clients (without jeopardizing your position or being unethical). Same with legal, consulting, and engineering and marketing careers … Get a few clients on the side and see how it feels. From there the choice is yours whether to stop, keep the side hustle, OR grow your own business.

What do you want to be remembered for the most?

In business 🡪 taking calculated risks … being well thought out … resilient … hard working … and creative. In life 🡪 I would want to be remembered as a good son, good sibling, great husband and father, reliable, and a good companion.

How can our readers further follow your work online? and any updates will be on Linkedin.

Thank you so much for sharing these important insights. We wish you continued success and good health!



Pirie Jones Grossman
Authority Magazine

TedX Speaker, Influencer, Bestselling Author and former TV host for E! Entertainment Television, Fox Television, NBC, CBS and ABC.