Transforming Ideas Into Market-Leading Companies
Three-time tech CEO. Harvard Business School lecturer. Author of Unlikely Entrepreneurs.
About
About Lou
Lou Shipley is a technology executive, company builder, and educator with over three decades of experience scaling businesses from startup to exit. As a CEO, he has led multiple venture-backed companies through growth and acquisitions totaling nearly $1 billion in value. Today, he teaches at Harvard Business School and serves on the boards of several tech companies.
Career Timeline
Avid Technology
Managed U.S. sales territories, ran the Asia-Pacific business from Japan, and led Americas and Pacific operations as the company grew to $450M in sales.
WebLine Communications
Joined as the fifth employee and built the sales organization from the ground up, growing revenue from $0 to $15M in just three years. Acquired by Cisco for $325M.
Highland Capital Partners
Evaluated new ventures and investment opportunities at one of the top early-stage venture capital firms in the country..
Reflectent Software
Led the company as President and CEO through growth and a successful exit. Acquired by Citrix Systems. Acquired by Citrix.
VMTurbo (now Turbonomic)
Scaled the business dramatically, growing from 25 to 420 customers and from 30 to 100 employees in two years, establishing the company as a leader in virtualization management. 25 to 420 customers.
Black Duck Software
Led an open source security and compliance company to market leadership, driving 400% revenue growth. Acquired by Synopsys for $565M.
General Catalyst
Served as an Executive in Residence with the venture capital firm, advising portfolio companies and evaluating new investment opportunities..
New Book
Unlikely Entrepreneurs
Unlikely Entrepreneurs: Wins, Losses, and Crucial Lessons on Building Great Companies
By Lou Shipley & Patricia Favreau
Available February 3, 2026
Combining decades of expertise from Harvard Business School and MIT Sloan, this book profiles 50+ entrepreneurs across industries, from Bill Warner (Avid Technology) and Katie Couric & John Molner (Katie Couric Media) to Liz Elting (TransPerfect) and Scott Ginsberg (Titan Casket).
It covers market research, go-to-market strategies, fundraising, leadership, pivoting, and AI-driven marketing, the practical ground you need to build a great company.
Featuring entrepreneurs including
Praise for the Book
What Leaders Are Saying
“A masterful blend of academic rigor and real-world wisdom. This book is an indispensable guide for anyone daring to build something great.”
Jeffrey J. Bussgang
Harvard Business School
“Full of formulas for success and life lessons that every entrepreneur needs to hear. A must-read for founders at any stage.”
Danny Meyer
Union Square Hospitality Group
“This book captures what founders need to know right now. Practical, inspiring, and deeply informed by real entrepreneurial journeys.”
Bill Aulet
MIT Entrepreneurship
Academia
Teaching & Academic Leadership
An entrepreneur who brings decades of hands-on sales leadership into the classroom, teaching the next generation of business builders at Harvard Business School and MIT Sloan.
Harvard Business School
Senior Lecturer, Business Administration
Teaches four sales courses across two academic units, giving MBA students the frameworks and hands-on judgment to build and scale go-to-market teams at startups and growth-stage companies.
Courses
HBS catalogCase studies developed on Wasabi and Katie Couric Media.
MIT Sloan School of Management
Lecturer
Brings decades of entrepreneurial sales experience into the classroom, giving students direct exposure to the strategies, negotiations, and leadership decisions behind startup growth.
Pairs academic theory with go-to-market practice, drawing on firsthand experience building enterprise sales organizations from the ground up.
Trinity College
Board of Trustees MemberMade a foundational gift in 2022 to establish the Trinity College Entrepreneurship Center, which supports student entrepreneurs on campus.
Speaking
Keynotes, Offsites, Sales Kickoffs and even Commencement addresses
Lou can speak on a variety of topics — entrepreneurship, education, sales and go-to-market strategies, leadership and culture. He draws on decades of experience in startups, as a three time software CEO, board member, advisor, and MIT and HBS lecturer.
Trinity College 200th Commencement Address
Lou returned to his alma mater to deliver the commencement address at Trinity College's 200th Commencement, sharing lessons from a career building and scaling technology companies.
Read the full address
Address to the Trinity College Graduating Class of 2026
By N. Louis Shipley ’85
President Lugo, Board Chair Bisaccia, trustees, members of the faculty, parents, families, and remarkable members of the Class of 2026: It’s an honor to speak with you today. Commencement speakers often quote famous people in their remarks. One of my favorite quotes is from FDR, who said on the topic of public speaking: “Be sincere, be brief, be seated.”
That’s my plan.
So, congratulations! This is a big day, a milestone not just for you but for everyone who has invested love, support, and belief in your journey. Please remember to thank your parents, mentors, and friends, those who stood by you and helped you reach this moment.
Forty-one years ago, I sat where you are now. Many things in my life have changed—but much remains the same: I still have the same girlfriend, but she did eventually agree to marry me. While much of this campus has undergone a dramatic transformation, from this vantage point, the Main Quad, Long Walk, and Chapel have not changed, just as the remarkable value of your Trinity education has not changed.
You’ve earned your degree, but I encourage you to see today as an important milestone in your education and not as the end of it.
According to David Andres, Trinity College’s chief data and analytics officer, each year, roughly 553,000 American students graduate from liberal arts colleges and universities, and roughly 20 million Americans have liberal arts degrees. While this sounds like a big number, it’s only about 5 percent of the population. So, you’re actually a part of a very small and important group.
I’m still surprised I got into Trinity. I was put on the waitlist and needed financial aid, so it didn’t seem likely I would attend. Fortunately for me, though, through the generosity of generations of Trinity alumni who have supported the school and built the endowment that enables financial aid, I was able to matriculate.
By the way, I played on the hockey team when I was here. The team even won the ECAC championship—(the year after I graduated).
I’ll talk about three topics: how you can combine an entrepreneurial mindset with your liberal arts degree, how entrepreneurship united with passion and compassion can make a difference in the world, and the value of Trinity’s remarkable community.
Let’s dive into entrepreneurship and the liberal arts.
The resilience and intellectual agility cultivated in a liberal arts education lay the foundation for entrepreneurialism. Throughout my career, I have hired many liberal arts graduates—of different ages and from different backgrounds—and have rarely been disappointed. Your Trinity degree will help you navigate changes, learn new roles, and reinvent yourself throughout your career. I know what liberal arts grads are capable of: You write well, think critically and creatively, and ask great questions. Your liberal arts degree equips you to thrive in the era of AI. You work well on teams. Most importantly, you know how to exercise judgment. And I’ve always appreciated Trinity alumni for their emotional intelligence, their EQ, as much as their IQ.
In hiring, I was not concerned about a student’s major. Instead, I sought out people with a pattern of continuous improvement and coachability. And these English, history, econ, computer science, and art majors did well in a variety of jobs—marketing, sales, software development, finance, and customer support. You name it, a Bantam can do it. Know that the value of your degree is not just in what you studied here but also in the fact that you learned how to think critically, creatively, and independently.
My Trinity liberal arts education helped me reinvent myself from salesperson to CEO to full-time faculty member. I began my career in academia writing cases for MIT Sloan. Eventually, the professors I was writing for asked me to teach the class. I did and loved it.
I’ve been told I have an entrepreneurial mindset. I think I see opportunities where others see obstacles, and I’m willing to act despite uncertainty. I urge you to be entrepreneurial. You don’t have to start a business to be entrepreneurial, but you should be adaptable and open to learning from others and be willing to get outside your comfort zone. I’ve spent my entire career with entrepreneurs, and what sets them apart is their relationship with failure. They don’t see failure as the end—they see it as a chance to learn, to adapt, and to grow. They don’t see the world as a zero-sum game. They have grit, and they persevere. They might hit a stumbling block, but they retain control over their attitude. As Viktor Frankl, author of Man’s Search for Meaning, noted:
“Everything can be taken from a person but one thing: the last of the human freedoms—to choose one’s attitude in any given set of circumstances, to choose one’s own way.”
After my sophomore year, to help pay for school, I took a 100-percent commission job selling dictionaries door-to-door. I recall working a 12-hour day without making a single sale. I called these “character-building days.” As I reflect back on that experience, while I did earn money to finance my Trinity education, the real value was learning how to deal with rejection and failure.
Many years later, I was fired as the CEO of a tech company. I was devastated and thought I would never get another CEO job. I had to develop resiliency in the face of failure. It is likely that you, too, will experience failure in some form, but that’s OK. My desire to overcome failure drove me. Neil Simon, the famous playwright, once said: “Failure gets me up earlier the next morning than success. If you get right back to work, yesterday’s pains become today’s inspirations.”
Now, let’s talk about passion.
At Trinity, I developed a love of history. But when I got to graduate school, I found a new passion. I took a course called “Entrepreneurial Finance,” where I learned how to fund a start-up: how to create something from nothing, how to finance an idea. I couldn’t believe how enthusiastic I was to learn more about this. A whole new world opened up before me.
Since I didn’t have an idea for launching a business, I searched for start-ups to join. I read an article titled “Small Companies Going Global,” which was about Avid Technology, the pioneer in digital video editing. Since I had sold books door-to-door, I wasn’t afraid to cold-call Avid’s Founder, Bill Warner. When I got him on the phone, he told me, “Lou, you seem uniquely unqualified for a career in technology. You went to a prep school, studied liberal arts at Trinity, worked on Wall Street, and then went to Harvard Business School.” I asked to meet him in person. We met and hit it off, and he hired me as a consultant. I knew little about film, video, or audio and even less about computers and software. My passion for learning and the skills I acquired here enabled me to overcome this lack of industry-specific knowledge. By the way, never underestimate the value of an in-person meeting. I got that job.
One day, Avid’s CEO asked me if I would consider looking after the company’s Asia-Pacific business, an offer that intrigued me. Japan was the biggest market in Asia, so I began traveling there, selling, and studying Japanese. My liberal arts experience gave me confidence that I could learn about a new culture and develop a working knowledge of a new language.
My wife Amanda and I moved to Japan and loved it. Our son Clarke was born in Tokyo. The business flourished, and I opened our subsidiary in Tokyo, then additional offices in China, Singapore, Hong Kong, and Australia.
My entrepreneurial mindset—which began in the liberal arts classroom, combined with my passion for start-ups—led to an experience of a lifetime. I urge you to follow your passion.
Passion is a force that can transform obstacles into opportunities and setbacks into fuel for growth. If I could give you one piece of advice, it would be this: Pursue your path with wholehearted passion. Whatever you choose—business, education, law, medicine, public service, or nonprofits—throw yourself into it with energy and purpose.
Now, for compassion. Trinity alumnus Marvin Pierre, Class of 2006, lives a life of passion AND compassion. Marvin grew up in South Jamaica in Queens, an underserved New York City neighborhood. His parents instilled in him that education and lifelong learning were the way to build a better life. Marvin told me that he remembers a homeless man nicknamed Jungle who, as Marvin walked past him each day on his way to school, would say, “Stay in school, young man.” He realized then that, if you’re paying attention, mentors can present themselves in unexpected ways. Marvin excelled at school and got a scholarship to Tabor Academy, a prep school in Massachusetts. Tabor was a real adjustment for him, and he initially struggled in school. Then he met Sam McFadden, who volunteered at Tabor and mentored students who were struggling, students like Marvin. Dr. McFadden told him something that he would never forget: He said, “Lift as you climb.”
Marvin graduated from Tabor and then Trinity and worked on Wall Street for Goldman Sachs. Success by almost any measure. But when a Tabor alum asked him to share his story at a Brooklyn school not far from where Marvin grew up, Marvin questioned the meaning of the numbers that appeared by each student’s name. His friend said they represented each student’s reading comprehension level. The low-number kids haunted Marvin. His gut told him those kids were more likely to drop out of school, perpetuating a cycle of poverty and potential incarceration. He knew that his real passion was education. So, he walked away from Wall Street. He took on the role of assistant principal at a Houston high school. But he knew underserved kids from challenging backgrounds needed support beyond what public schools could provide. Marvin then founded Eight Million Stories, an education center that provides underserved students with the support and resources they need to learn vital skills. All the students who have graduated from Eight Million Stories have earned their GED and honed skills to make a good livelihood. And others have gone on to college. Eight Million Stories is thriving.
How does all of this tie together? Marvin exemplifies what it means to have passion and compassion. He understood others’ misfortunes and was committed to building an institution that can help alleviate them. His passion, resilience, and intellectual agility enabled him to launch a nonprofit, to tackle setbacks, to pivot when necessary, and to scale what he created. Marvin is but one of many amazing members of our Trinity network.
And this leads us to the topic of embracing the Trinity community.
There’s a saying that you are known by the company you keep. Your Trinity contacts are a great foundation for the personal and professional relationships you will build as you progress in life. I urge you to grow, nurture, and celebrate these relationships. They will become a source of pride and emotional support. Consider this a project of “netweaving” more than networking. Weave a fabric of strong, interconnected relationships based on trust, content, and shared experiences. Support the College and give whatever you can; it’s really important. On that point, congratulations on the Senior Class Gift! I understand 68 percent of you contributed. That’s terrific.
My Trinity relationships have surrounded and supported me. Barney Corning, a hockey teammate, was my best man; John Molner, my roommate, was the protagonist in a Harvard Business School case study. Treasure your friends, acquaintances, and even Bantams you don’t know. My passion for entrepreneurship and Trinity motivated me to give the founding gift to what will be the College’s Elting Center for Innovation and Entrepreneurship. The backhoe starts digging on Vernon Street tomorrow! I encourage you to come back and visit this center. I know your experiences will be of great value to future students.
As a trustee, I have witnessed year after year how the College continues to find a new generation of leaders who join the board with generosity and purpose. This spirit of service and dedication is the heartbeat of our College. You are now part of this legacy—ready to make your own mark, to give back, and to inspire those who follow.
As you venture out into the world, take your liberal arts degree and entrepreneurial mindset, combine those with your passion and compassion, and always remember that you are forever part of the Trinity College community. And as you move forward and achieve success, I urge you to take Dr. McFadden’s words to heart: Always remember to lift as you climb. Reach back, and help others rise.
What Lou Speaks On
Tech Sales & Go-to-Market Strategy
Frameworks for building repeatable sales processes and launching products that gain traction in competitive markets.
Building and Scaling Startups
Insights from decades of founding, growing, and advising technology companies from early stage through successful exits.
Leadership in Technology
How to build strong teams, encourage new ideas, and lead through fast change in the technology sector.
Open Source Security
The opportunities and risks of open source software, with lessons from leading Black Duck Software through its acquisition.
Entrepreneurial Management
Practical strategies for entrepreneurial leaders, drawn from teaching at MIT Sloan and Harvard Business School.
Interested in booking Lou for your event?
Keynotes, panels, fireside chats, and workshops available.
Boards & Investments
Advising and Investing in What's Next
Lou serves on the boards of directors and advisory boards of technology companies, and invests in early-stage businesses.
Board of Directors
3 companies
Advisory Boards
10 companies
Private Investments
9 companies
In the Press
News & Media
Coverage of portfolio companies, leadership news, and Lou's work across the industry.
Published author of Unlikely Entrepreneurs, written with Patricia Favreau.
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Let's Connect
Whether you're interested in a speaking engagement, a board opportunity, or just want to connect, reach out below.