Lewis Gersh – Founder & CEO, PebblePost

Lewis Gersh is founder and CEO of PebblePost®, guiding corporate strategy and company vision with over 20 years of board and executive management experience. Prior to PebblePost, Lewis founded Metamorphic Ventures, one of the first seed-stage funds, and built one of the largest portfolios of companies specializing in data-driven marketing and payments/transaction processing. Portfolio companies include leading innovators such as FetchBack, Chango, Tapad, Sailthru, Movable Ink, Mass Relevance, iSocket, Nearbuy Systems, Thinknear, IndustryBrains, Madison Logic, Bombora, Tranvia, Transactis, and more. Lewis received a B.A. from San Diego State University and a J.D. and Master’s in Intellectual Property from UNH School of Law. Lewis is an accomplished endurance athlete having competed in many Ironman triathlons, ultra-marathons, and parenting.

About PebblePost

PebblePost is the leading digital-to-direct mail marketing platform. We capture online interest and intent data to send relevant direct mail that activates buying decisions at home and drives conversions everywhere. We invented Programmatic Direct Mail® to help brands convert more shoppers into buyers using advanced targeting, algorithmic optimization, attribution, and quantitative analysis. PebblePost is a venture-backed company based in NYC.

How did the concept for PebblePost come about?
Prior to founding PebblePost, I worked for over 20 years as an entrepreneur, venture capitalist, and startup executive. My background is in digital and programmatic advertising, and dates back to its earliest days.

By 2014, I had left my fund to go back to the operating side and was thinking about all things “programmatic” and wondering if I could find a new channel to own for it. This was on my mind as I retreated to one of my favorite places to think: my farm in upstate New York – call it free-range thinking. I was cutting some hay on my tractor, running all these various programmatic scenarios through my head, when it hit me, “What about direct mail? It’s the second-largest ad spend next to TV, has the highest response rate of any media, and there’s been no new product in 25 years…”

I realized there was potential to start with retargeting and then use data to continuously enhance the efficiency and efficacy of a marketer’s goals. By infusing digital intent data with direct mail, we could bring the best of digital marketing to the physical world—and create the first new marketing channel since search and social. That was the beginning of Programmatic Direct Mail®, and how PebblePost became the first and leading digital-to-direct mail marketing platform.

How was the first year in business?
We spent our first several months defining the vision and creating a product and market development roadmap. In truth, we probably spent more time than most updating and refining it because we were creating not just a new product, but a whole new marketing channel. Nothing like what we were doing had ever been done before, so there was more to plan and map out upfront.

When we first started talking to investors, we were not greeted with enthusiasm. Not surprisingly, there had never been a venture-backed direct mail company. Most of the professional VC firms had lived through the nadir of direct mail back in the 1970s, when it was roundly (and often rightly) castigated as “junk mail.” In fact, an investor from one of the biggest and most respected funds in the Valley had one of the best responses to our pitch. He said, “Great, just what the world needs – automated junk mail.” We certainly had our challenges, but I believed in a very simple and concise pitch, delivered in just one bold, memorable sentence. I said, “I have a 7-syllable pitch for a billion dollar opportunity: Programmatic Direct Mail®.”

In the first 9 months, I was pitching brands, gathering info, and communicating back to the team. We would then spend hours digesting, designing, planning, building, and testing aspects of the product with dynamic and fluid iteration. We wanted to get as much feedback as possible and we used that feedback to continue enhancing the product. Between pitches and internal reviews, I was averaging 120-130 meetings a month!

We were able to get 9 brands live before the first holiday season – and it worked! We saw the initial results off of recognized customer remarketing and the conversions were off the charts. What’s more incredible is that we ended that first year with only an 8-person team.

What was your marketing strategy?
Our overall strategy is to position Programmatic Direct Mail® as a key technology that unlocks both the efficiency of digital marketing and the efficacy of direct mail. Brands can significantly boost performance by delivering a relevant and respectful message to shoppers who have shown the highest propensity to convert. We use our “90 / 90 / 90” thesis to explain the appeal and success of Programmatic Direct Mail, which is as follows:

1) 90 percent of actionable 1:1 intent data is now online.
2) 90 percent of meaningful purchase decisions are made at home.
3) 90 percent of purchases are made in the physical world.

PebblePost follows this construct by capturing online intent data and sending relevant direct mail that activates buying decisions at home and drives conversions everywhere.

How fast did the company grow during the first few years?
We built out the full 1.0 product set with continual feedback from the market, and I’m pleased to say demand was extraordinarily high. As we went live and began testing new things, we learned more and more, but it also put more and more load on our small team and platform. However, with that kind of demand, we quickly saw hockey stick growth—at one point generating 50x revenue growth in a 6-month period!

I believe this kind of growth is a testament to how the martech landscape is changing. More brands, particularly challengers and disruptors, are looking beyond digital and embracing new physical touchpoints on the path to purchase that help disrupt the typical shopper experience. This includes leveraging the best parts of digital and traditional marketing tactics to make a meaningful impression on shoppers in the physical world. When delivered in a relevant and respectful way, direct mail can help keep brands top of mind and part of meaningful household conversations that drive consideration and conversion.

In particular, we’ve seen a lot of interest with direct-to-consumer (DTC) and digitally-native vertical brands (DNVBs), which often struggle to find cost-effective ways to create physical-world touchpoints for shoppers. At PebblePost, we feel a kinship to these companies, since they’re often challengers of the status quo, just like we are.

How do you define success?
The definition of success can vary depending on your goals. For me, success involves producing the most relevant and respectful marketing communication for consumers, while also delivering highly-efficient and effective solutions for marketers.

I also think success means building a top-notch team culture and creating intrinsic value that rewards all of our employees, their families, our investors, and our board.

It’s so important to learn and grow from whatever feat you set out to accomplish or experience. As a technology provider, much of our success is witnessed through the success of our clients—when they extend their campaigns because they’ve outperformed their own expectations, or when they see how our technology is enhancing their sales growth.

What is the key to success?
You should always hire people who are smarter than you and different from you. It’s the key to maintaining a competitive edge, and promotes continued learning, great problem solving and knowledge-sharing. When you challenge yourself (and your team) beyond the scope of the imagined, that’s when you see what’s truly possible.

Equally important, every team needs strong communication. It’s essential for building culture, eliminating friction, and identifying/addressing challenges as quickly as possible. It also helps to establish priorities and ensure that all team members are on the same page, rowing in the same direction.

What is the greatest lesson you’ve ever learned?
An investment banker who wrote the first check in my first venture once told me that when it comes to innovation, there’s one general rule to live by: “It takes twice as long to produce half as much at twice the expense.” So, whatever you think you’re going to accomplish, make sure to adjust by those metrics to set proper expectations.

What are some quotes that you live by?
“Where technology controlled the use, use now controls the technology.” – Ithiel de Sola Pool

“If you don’t like change, you’re going to like irrelevance even less.” – General Eric Shinseki

“Investors love good news and they can handle bad news, but they will not tolerate surprises.” – My Dad

What are some of your favorite books?
As it relates to communications, I’m currently reading Cybersemiotics: Why Information Is Not Enough and loving it.

My other go-to books often center around endurance, or an epic voyage—I’m a triathlon runner, so endurance is a theme throughout my hobbies. My top reads include Endurance: Shackleton’s Incredible Voyage, In The Kingdom of Ice, The Long Road, and A Higher Call.

For my news, I rely on The Economist, The Atlantic, The Wall Street Journal, Nature Magazine, Physics World, and Scientific American.

Tell me about one of the toughest days you’ve had as an entrepreneur.
Which one? Ha!

One of my toughest days as an entrepreneur was back when I founded Gersh Venture Partners. We had just added our first partner and were going to market to close an early seed-stage venture fund called Metamorphic Ventures. I was at my farm upstate when I sent out our first close announcement to all investors, not knowing that in NYC, Lehman Brothers had just announced bankruptcy, starting the global recession. That one day set the fund back a year and cost an enormous amount of money and stress.

When faced with adversity, what pushes you to keep moving forward?
I give all the credit to our positive and hardworking team at PebblePost. They help to maintain a fundamental atmosphere of enthusiasm. Working with so many bright people who share a strong belief in the technology we’re developing makes dealing with challenges a little less difficult. I’ve also been in the industry for over 25 years, so I’m able to lean on my past experience to help push past adversity. In the end, I also recognize that everything worth anything comes with effort and patience.

What advice would you give to young entrepreneurs?
Be thoughtful about your business choices and find people who believe in you as a person. Also, do not be discouraged by rejection.

When beginning PebblePost, I heard more no’s than yes’s, but it was the relationships I had built over my career and the people who warmed up to my ideas that ultimately helped me get the company off the ground, and these people continue to provide valuable insights to help keep us moving forward.



This interview was brought to you by Audible. Try a 30-day free trial and receive two free audiobooks!

This interview was conducted for research purposes by author Jason Navallo for his upcoming book, Underdog.

Check out our Books page to see the top books recommended by entrepreneurs, professional athletes, and executives.