Michael Loeb is a serial entrepreneur and the founder & CEO of Loeb.nyc.
After starting his career at Time Inc., Michael co-founded the Synapse Group with then partner, Jay Walker. Under Michael’s direction, Synapse grew to become the largest seller of consumer magazine subscriptions worldwide, with its patented credit card-based Continuous Service model. Michael and Jay went on to incubate Priceline.com at Synapse, leveraging a shared team of operations and capital.
When Synapse Group was sold to Time Warner for $800mm in 2006, Michael formed Loeb Enterprises with partner, Rich Vogel to ideate and develop new business concepts. The largest of those ventures was ScriptRelief, a first of its kind pharmacy discount provider that has a membership in excess of 12 million Americans which saves patients billions on their prescriptions. ScriptRelief was recently sold to United Healthcare for an undisclosed amount.
As of 2019, self-funded Loeb Enterprises, rebranded to Loeb.nyc, is building and managing a portfolio of over 20 curated companies, most of which are domiciled at Loeb headquarters in Manhattan and half of which are executions of Loeb concepts. Under Michael’s leadership, Loeb.nyc has established a new model for startups. By pairing exceptional strategic and executional talent with passionate founders, and CEOs plus capital Loeb.nyc significantly derisks startup launches of the 20 companies, Loeb expects enough bonafide unicorns to populate a small corral.
Q & A with Michael Loeb
Michael R. Loeb ’77 P’21 was a psychology major at Amherst and captain of the wrestling team. Which seems fitting: as a self-proclaimed “serial entrepreneur,” Loeb thinks hard about why people behave the way they do—and grapples with strategies to make their lives better. He is the Founder and CEO of Loeb Enterprises, which has backed, funded or built more than 50 thriving companies, including The Synapse Group and Priceline.com. He also sponsors the Loeb.nyc Summer Internship Program for college students passionate about business and innovation.
In 2016, Amherst’s Career Center became the Loeb Center for Career Exploration and Planning. The name honors a seven-figure gift that helped ensure that “The Loeb” (as everyone now calls it) would become an ever more vibrant hub for career exploration. Katharine Whittemore, Amherst’s senior writer, sat down to chat with Michael Loeb about everything from entrepreneurialism to class to careers to the liberal arts.
So why don’t I just start and ask about your connection to the center that bears your name. Why make an investment in career development at Amherst?
Well, Amherst has changed as society has changed. So the thought behind the career center is that, very early in the curve, we get students thinking about career and focusing on obtaining the building blocks they’ll need to be successful post-graduation.
Back when you were a student in the 1970s, I understand that career counseling at Amherst was about non-existent.
The presumption at the time was that you had an uncle in the banking business, or a lawyer, or a consultant, and they could give you the entry that you needed into your first job. So there wasn’t a lot of focus on career because your career was all but assured before you even matriculated into Amherst College. If you turn back the clock to when I went there, many of the kids went to prep schools, and came from the most elite segments of society. I was a little bit of an exception because I was a public school kid who spent most of his time in Queens.
The nature of work was very different then. We would, say, join IBM as a newly minted graduate of Amherst College and we would retire at mandatory retirement age of 65 without ever-changing jobs. The thinking was you’re gonna spend 40 years or more at one company. Switching jobs was much more the exception than today. Therefore, a lot of the career support that we now have and find necessary was unnecessary back in the day of a very different Amherst College.
What was your own thought about a career when you were nearing graduation at Amherst?
I didn’t think a whole lot about it. My dad [Marshall Loeb] had worked at Time Inc. as a journalist, and I spent a couple of years avoiding Time Inc. Eventually I capitulated, but went not into the company as a journalist, but as a business person not having quite the inclination nor talent to become a journalist.
And Time Inc. remained a very Ivy-League-centric place. My dad was Jewish and from Chicago and went to the University of Missouri, and so he didn’t check any of those boxes, but fought his way into Time Inc. and moved from the bottom rung of the ladder to the top and retired as the managing editor of Fortune magazine, a position that he held for ten years. That was his unusual trajectory. He was kind of a champion for equality and was an example of someone who didn’t have the benefit of elite schooling or an elite family but was nonetheless successful.
Let me get your thoughts on entrepreneurship, because I know that’s a subject dear to your heart.
The highest and best use of capital in this country is intellectual capital. And that intellectual capital has been at the core of companies like a Google, a Facebook, Microsoft, Netflix…these are the engines that are powering our economy.
Jobs at Fortune 500 companies are down and they have been bested by entrepreneurs that have built companies and hired people. So I think we have never seen a time of greater change, greater disruption. And very large companies can do many things very well. Being small and nimble and able to move quickly and build things quickly gives the entrepreneurs unique advantages.
Let’s talk about Amherst as a place to encourage and help entrepreneurs. Where are we at and where do we need to get to?
So Amherst has embraced entrepreneurs. And it’s been a process. When I was first asked to talk to the entrepreneur club of Amherst maybe twelve years ago, they were pretty much an underground society. They were not embraced by the faculty or the administration. A lot of that has really, really changed. Not only with Amherst, but also other colleges. Before, educational institutions had a disregard for entrepreneurs because they thought their mission was really building people to work in fabulously successful but large companies and become part of the status quo.
But we’ve come a long way. What does Amherst do very well and why is an Amherst student attracted to Google? The answer is that Google wants great athletes, and in this case, I mean great mental athletes. People who can think out of the box, people who can draw from different fields of study. They need people to have alacrity. They need people to think flexibly and nimbly and draw experiences and anecdotes from vastly different fields of play.
They just don’t want baseball players or football players, they want great athletes who can do just about anything. And a liberal arts background is, I think, perfectly fitted for the type of mental gymnastics that you need to do to be truly inventive.
Let me ask you about the Loeb.nyc Summer Internship Program, in which you place interns in startups.
We had 1500 applications for 40 spots, mostly rising seniors. Of the 40 spots, only 20 are placed in a Loeb company, and the others are placed in outside companies, all start-ups. We pick them very carefully. We want just the right business model, management teams, attitude and a meaty summer project.
We start the summer off with something we call “Intern-a-topia” which begins with our version of entrepreneurs’ boot camp. We try to re-educate the students for the start-up world. In college, you can meet a professor one-on-one for an hour. You’re not gonna be afforded such a luxury working for a start-up because everyone’s running around in these tiny companies with their hair on fire.
So two days of entrepreneur bootcamp at Intern-a-topia with the last day a matching exercise. Think The Bachelor, except you match interns to start-ups. The entrepreneurs get ten minutes to pitch to the students about their business, and then the students pitch themselves to the entrepreneurs. Each side picks their favorites. The final matches are made, hugging is involved and pictures are taken. Then they sit down next to one another at dinner, that Saturday night, and work starts on Monday.
Michael, if you were going to advertise your own company—Loeb Enterprises and Loeb.nyc, aka “the company factory”—as a career path for a current or future Amherst student, what pitch would you give?
You have the chance here to help build a company that might just change the world for the better.
I’d like to unpack a little bit of what you said about the liberal arts. Is there something about the flexibility, the ability to question, within liberal arts that works for being an entrepreneur?
What works is people who think, right? And it’s a full contact, multi-disciplinary activity. And that’s what a liberal arts education does. And so if you’re an engineer and all you do is learn how to code, that’s not enough. You don’t have that rich, and enriched thinking process that you do when you go to Amherst College. I think Amherst teaches you how to think and that’s probably the greatest gift that any educational experience can give you.
Let me bring you back to the Loeb Center itself. How are you feeling about what The Loeb is doing and what else you want it to do?
Well I think it has made incredible strides and terrific progress, and I’m very pleased with the trajectory. You have people at the Loeb Center who are committed and devout, and they think 24/7 about how to make it better, how to improve the career trajectories of the students at Amherst College. I couldn’t be more pleased or proud.
Careers and the Liberal Arts (Nov. 21, 2016)
Name Change for the Career Center (Nov. 2, 2016)
Mindful of Mission, Career Center Gains a New Name (Sept. 14, 2016)