👉 Next: check out Jesse’s AMA with Horizonites👈

🔑 Key Lessons 🔑

  • Work with people you trust: Jesse, Nick, and Chris (Wharton classmates who had known each other since freshman year at Penn) built 200 person digital-marketing giant Ampush from scratch after quitting their jobs at McKinsey, Morgan Stanley, and the Carlyle Group.
  • Hustle hard: Like how the Airbnb founders sold cereal boxes, Jesse started selling McKinsey style research decks on the ad-industry for $5,000 each, generating $150,000 for Ampush.
  • Commit no matter what: When Ampush had $50k in credit card debt and and their ad campaigns were burning cash, Jesse’s friend at Google said to him “Google doesn’t even know how this business works. Why didn’t you call me before you started doing this.” The situation felt hopeless, but the team marched on.
  • Success is around the corner: Ampush has worked companies like Lyft, Dollar Shave Club, Uber, and MasterCard.

SAN FRANCISCO — The Horizons speaker series brings in experienced entrepreneurs, investors, and technologists to share their unique perspectives with the next generation of technology leaders. 

Speaker Background

Jesse co-founded Ampush in 2009 and serves as its Chief Executive Officer. Previously, Jesse worked as an Investment Professional at Goldman Sachs in New York and as a Consultant at McKinsey & Company in New York and Dubai focusing on the internet media, e-commerce and telecom industries. Jesse is a Member of the Advisory Board of Blue Collective and currently serves as an advisor at Milo.com. Jesse earned a B.S. from the Wharton School at the University of Pennsylvania with a dual concentration in Finance and Entrepreneurship from 2002 to 2006 and a second degree in Political Science. He also earned a B.A. in Political Science from University of Pennsylvania between 2002 and 2006.

Time and time again at the Horizons Speaker Series, Jesse has told our students that a great idea does not set a team apart. Big markets to tackle are easy to identify. Just because you’re smart, does not mean you can build a big company, and that being too smart is going to cause you more harm than good.

According to Jesse there are only 3 things you need to worry about: who you work with, commitment, and tenacity.

This article is about why these are the only things that matter in building a successful company.

Necessity and time breed great entrepreneurship.

tldr: Jesse says thinking about starting a company is an essential first step before starting one.

Something you have to understand about Jesse is that entrepreneurship runs in his blood. His father was an immigrant and entrepreneur and seeing his father building a business had significant impact on Jesse’s own entrepreneurial journey.

Seeing his father building a business had significant impact on Jesse’s own entrepreneurial journey.

For Jesse, there is a mentality around being a 2nd generation entrepreneur – having to be scrappy, having to prove yourself, and having real stakes on the line that really motivates him.

Jesse believes there is no such thing as natural talent when it comes to entrepreneurship – that compounding entrepreneurial insight over many years is the most powerful thing in the development of entrepreneurs.

“It takes ten years after you first entertain the idea of entrepreneurship to when you’ll be ready to start a great company.” 

Jesse’s first foray into entrepreneurship

Jesse first got into entrepreneurship during the internet bubble when he saw his dad investing in companies like Yahoo and Dell. After, he needed to get a taste of starting companies himself. So, in high school he started DJ’ing and cornered the Indian wedding market – a very fun and lucrative place to start an enterprise.

Building trust with co-founders in college

tl;dr: The great myth of entrepreneurship is that the right idea or tackling the right market will lead to success. The truth is your startup will live or die by the first five people you work with.

Jesse met Nick Shah and Chris Amos, his eventual Wharton classmates and co-founders of Ampush, in a summer program at the University of Pennsylvania called Leadership in the Business World.

Eventually, they all ended up in consulting and banking and developing very similar analytical skill sets. Jesse worked at Goldman Sachs and McKinsey, Nick at Morgan Stanley, and Chris at the Carlyle Group.

The group all ended up at Penn’s Wharton School and started an on-campus t-shirt company called Shirt Guyz. They realized that college kids spent a lot of money on shirts. Whether it was sororities or clubs, lots of custom shirts were appearing all over campus. With this sudden realization they got into the shirt business by charging $7 for a shirt that cost them $2 to make.

They were prolific across campus, making shirts for all the different clubs and organizations at Penn. Soon, they had $200k in sales and 15 employees.

Then came their big break.

There is an event at Penn called HeyDay. It is arguably the most notable tradition the junior class has and serves as a “moving-up” ceremony to mark the advancement of juniors in to seniors. Thousands of students march around campus sporting fake straw hats, red t-shirts and canes.

Hey Day at Penn

Jesse and the team had pitched the Penn class president to make a $10,000 order for the 2,500 to-be seniors at Penn for Heyday.

They got the contract!

They bid out the printing business to local printers and went with the cheapest guy they could find, someone they didn’t know that well. The guy comes back with hundreds of blue t-shirts even though the order specified red.

The class board along with the class president were freaking out at that point. The t-shirts were selling out faster than Jesse and the team could make them. Jesse was hearing about all of the delays, and the class board and president were calling him directly to figure out what was going on.

On a fateful and intense morning leading up to Hey Day, Jesse received a call from a Daily Pennsylvanian (Penn’s school newspaper) reporter asking what the heck was going on with the most important day of a Penn juniors life. Jesse explained everything the way he saw it.

“Nothing is going right. Orders are delayed. It is our worst nightmare.”

The next morning, a story in the Daily Pennsylvanian got published with Jesse’s quotes and the headline “A shirtless Hey Day?”

Headline in the Daily Pennsylvanian from 2005 about the missing t-shirts

For Jesse and the team, it was the end of the year, the middle of finals, and everything was going wrong.

Just when all hope seemed lost, they saw a tiny address on the shipping box that listed a FROM address in Philadelphia, where Penn is located.

Turns out, the contractor that Jesse was using to print was also re-selling the printing contract to another provider right outside of Philly. When they realized what was going on, Nick decided to skip his exams, Chris stayed on campus to sell whatever shirts remained, and Jesse and Nick raced off to the t-shirt printer, whom they’ve never met before, in the middle of the night.

They started throwing pebbles at the window of the printer business until the owners come out. Jesse explained the situation and the groups began debating outside, the Shirt Guyz goal was to drive back with the hundreds of missing shirts. The printers went back inside and the team started throwing more pebbles at the window until the printers finally agreed to print the shirts overnight. Nick and Jesse drove back and forth, continually dropping off order of 200 or more shirts to Penn nonstop through the night.

Jesse then had the pleasure of calling up the reporter and saying “print a retraction, all the shirts are delivered.”

The next morning, a story in the Daily Pennsylvanian got published with Jesse’s quotes and the headline “Shirt Guyz save HeyDay”

The retraction posted the next day!

The same thing happened with Horizons. Before Horizons started – Abhi, Darwish, and Jesse’s brother Vinny all worked on Altair prep together. Abhi and Darwish are still bringing that same energy to Horizons – along with Edward whom they also met at Penn and worked on high-stakes projects will time and time again.

The trials of co founders repeat themselves over and over again. Young entrepreneurs often meet co-founders in college, so our advice to future Horizonites is to seek out people like Chris, Jesse, Nick, and Abhi to work on projects with either at your school or at Horizons.

“Your company will live and die by the decisions your team makes. Idea and market matter much less than people.”

Why “smart” people don’t start big companies

tl;dr: If you’re a smart college kid, your brains work harder than your legs. When that is the case, commitment is the most important thing you can have.

Jesse, Nick and Chris, after realizing they loved working together, went on a building spree. They built a social network for high schoolers and and even had a conversation with Mark Zuckerburg who wanted to acquire the project, but they got burnt out and stopped.

They built a sports social network and pitched it to VCs, debating whether to drop out of school to work on the project full time, but school eventually got in their way.

The team was working on cool, fancy things, but they were not working seriously. They were smart guys jumping around from one shiny object to the next, knowing that no matter what happened their jobs at McKinsey and Morgan Stanley would be waiting for them alongside a prestigious degree from Penn on their resume.

One they realized that if they were giving so many years of their lives to companies like McKinsey and Morgan Stanley, they could at least give two years to themselves, things started to change.

They said for two years they would focus on Ampush. No GMATS, no LSATs, no applying to grad schools. All they had to lose was two years.

To this day Jesse attributes getting Ampush off the ground to two committed years of hard work from 3 smart guys. 

The challenges of starting a digital marketing giant

tl;dr: Everyone on the planet will doubt you – your parents, friends, and the market. Only urgency, aggression, and persistence will save you.

When Jesse graduated from Wharton he covered new media at Goldman Sachs and was exposed to the world of digital marketing. He received calls regularly from hedge fund managers and investors asking about the weird new world of internet advertising. In 2005 few people could answer questions like “what are Facebook and Google and how do they make so much money” quite like Jesse.

Jesse became the expert.

He started professionally consulting on GLG – an expert network that investors use to speak with specialists in a field – he charged $1000 an hour.

Jesse was charging $1000 an hour and became the digital marketing expert everyone wanted to speak with

But there was a long road from investor and part time consultant to turning Ampush into the growth marketing giant it would eventually become.

Ampush started out in the competitive world of performance marketing. The space is where 80% of Google and Facebook’s enormous revenues come from. Performance marketing is when a company that gets a lot of customers online pays another company (like Ampush) to acquire customers for them, and pays them for acquiring those customers.

Example: Netflix would pay Ampush a bounty for finding them a subscriber. Netflix gets the customer, Facebook or Google get paid a fee for serving ads, and Ampush is left to collect the ad-bounty.

With a few customers, the team started on their journey. They read every book about online advertising and marketing in the space to find their edge. They wrote python scripts, excel macros, and used sophisticated NLP tactics more similar to a hedge fund than a marketing company: buying and selling keywords on different ad exchanges.

To be profitable in their first campaign, they needed to convert 2% of customers on a $10k campaign for one of their customers. It was time to put all their research on the line.

They put $10k on an AMEX credit card (because of the “performance” nature of the business, at that point, Ampush had to front their own cash before they’d go get paid by the company and collect their bounties).

The problem was they didn’t perform. They got a .1% conversion. They needed to spend $100 to acquire a customer but they spent $1000 – they were getting destroyed in a business they thought they knew inside and out.

Jesse had left his fancy job to live with his parents for a company that in his words was “going to shit.”

Jesse spoke with his friend from Google to find an edge in the online ads space. She said “Google doesn’t even know how this business works. Why didn’t you call me before you started doing this.” Again, not very comforting.

When there is no comfort anywhere around you and no end in sight, Jesse will likely tell you the only way out is through. Every week, more and more, for the next two years, the Ampush team committed all they had.

The team talked to everyone on the planet in the online ads space to get an edge.

They spent more of their savings and more on credit cards, knowing if necessary they could go back to their jobs.

And on Jesse’s 26th birthday they made $100k in revenue and $30k in profit that month. 14 months later, they were making $2M in revenue and $800k in profit per month, with 10 employees. Soon after, Ampush became the first company to figure out advertising on Facebook and went on to spend over 300 million on the platform for its clients.

They had built a business with urgency, aggression, and persistence because they didn’t quit when times get tough.

Stop thinking about the cool ideas and the big markets. Think deeply about the people you want to work with and the problem you’ll approach with commitment and tenacity, day in and day out, for at least two years. 🙂


Our students ask speakers insightful questions. Check out Jesse’s conversation with Horizonites✨ here!✨

🎉 Congrats on making it to the end! 🎉

Horizons is where present and future tech leaders meet. Join us!. Also, check out the rest of our stories here. You might like something in there. You can email our admissions team here. 👏

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