Jeffrey Bussgang on Entering StartUpLand: An interview by Bob Morris

Jeffrey Bussgang is a venture capitalist, entrepreneur and entrepreneurship professor at Harvard Business School (HBS). His venture capital firm, Flybridge Capital Partners, has over $600 million under management and made investments in over 100 technology-focused startups since inception over fifteen years ago. At HBS, he teaches “Launching Technology Ventures,” a popular class for MBA students starting companies or pursuing careers in startups.

Prior to becoming a venture capitalist, Bussgang was an entrepreneur, serving as cofounder and president of Upromise (acquired by Sallie Mae) and an executive team member at Open Market (IPO 1996). He is author of Mastering the VC Game, an essential guide for entrepreneurs raising capital and building their startups, and, Entering StartUpLand: An Essential Guide to Finding the Right Job, as well as over twenty HBS case studies, teaching notes and book chapters on startup management and entrepreneurship. He started his career with The Boston Consulting Group and holds an MBA from HBS and a BA in computer science from Harvard College.

He writes a popular blog

www.SeeingBothSides.com

that has been syndicated in Fortune, Inc. and the Huffington Post and lives in the Boston area with his wife and three children.

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Before discussing Entering StartUpLand, a few general questions. First, who has had the greatest influence on your personal growth? How so?

My father. He was born in pre-war Poland and survived the Holocaust as a refugee and later soldier in the British Army. After the war ended, he came to the United States and earned his bachelors and masters from MIT and his PhD from Harvard. After a brief stint at a large company, he left to start his own company and bootstrapped it over 25 years before selling it successfully. I had the opportunity to earn a “kitchen table MBA” as a kid growing up and saw him as a role model as an immigrant, technology entrepreneur while also being an active community leader. Nearly all my personal, professional and civic activities have been modeled after his example.

The greatest impact on your professional development? How so?

Same answer!

Here are several of my favorite quotations to which I ask you to respond. First, from Michael Porter: “The essence of strategy is choosing what not to do.”

The ability to focus is one of the most and underrated qualities in entrepreneurs. We live in a world full of distractions and interruptions. When we come to an opportunity, there often appear adjacent opportunities in the form of bright shiny objects that catch our attention. Being able to block out these distractions and remain doggedly dedicated to the strategy, objectives and tasks at hand takes great skill and fortitude but represent attributes I consistently see in the most successful entrepreneurs.

From Richard Dawkins: “Yesterday’s dangerous idea is today’s orthodoxy and tomorrow’s cliché.”

Entrepreneurs are disrupters at heart. Disruptive ideas challenge today’s orthodoxy (if it were obvious, everyone would be doing it) and even seem inconsequential at times (summarize my thoughts in 140 characters? Sounds quaint but trivial.) But those ideas can become the mainstream very quickly. Think about the rapid adoption of cryptocurrencies such as Bitcoin and Ethereum as perhaps the most striking example of 2017.

From Ray Bradbury:  “First you jump off the cliff and you build your wings on the way down.”

I used a version of that quote, attributed to Reid Hoffman, in my first book, Mastering the VC Game: “falling off a cliff and building the engine on the way down.” The charm of the quote is that it captures the notion of a fixed amount of time to achieve something impossible and amazing. Entrepreneurs have to run multiple experiments in the search for product market fit, all while their limited cash is running down like an hourglass. If you can find that product market fit before running out of time, you will have the opportunity to soar.

Of all the greatest leaders throughout history, with which one would you most like to be engaged in one-on-one conversation for an extended weekend? Why?

There are so many but perhaps Chaim Weitzman would be my top choice. I was mesmerized by a biography of his. He was the ultimate entrepreneur: rising from his humble upbringing to create a movement (Zionism) and a nation (Israel) from nothing.

Looking ahead (let’s say) 3-5 years, what do you think will be the greatest challenge that CEOs will face? Any advice?

The last few years have seen an accelerated transformation in what is expected of business leaders, something I refer to as the rise of Compassionate Capitalism. Compassionate Capitalism involves two separate but powerful forces: first, the expectation that great companies and great leaders are mission-driven while adhering to a well-articulated set of values and, second, that great leaders will not be bystanders when political leaders or other business partners engage in behavior that is contrary to the organization’s mission and values. Today’s CEOs are facing a workforce and a customer community that demand these two elements in a visible, authentic fashion.

Examples in recent years include the resignation from the President’s Manufacturing Council in the wake of Charlottesville by Merck CEO Ken Frazier, followed by every other member of various business advisory councils, and the CEO outcry when the Indiana State Legislature passed the controversial Religious Freedom Restoration Act. Tomorrow’s CEOs are going to need to strike a delicate balance between serving as outspoken leaders regarding defending shared values in the broader community while at the same time be careful not to be seen as partisan. A daunting challenge indeed!

Now please shift your attention to Entering StartUpLand. For those who have not as yet read it, hopefully your responses to these questions will stimulate their interest and, better yet, encourage them to purchase a copy and read the book ASAP.

First, when and why did you decided to write it

I wrote the book after many years of answering the same set of questions from my students and other professionals seeking to enter StartUpLand. I was struck that while there were many, many books available for founders (including my own, Mastering the VC Game), there were no books available for joiners. Joiners are employees numbers two through two thousand who team up with the founder and their brilliant idea and strive to create an operating business. My mission with the book is to help joiners learn how to get in to startups and what the jobs are to be done.

In my review of the book for Amazon US, UK, and Canada as well as for other websites, I express my opinion that its subtitle could describe it as a guide to find “the right fit” rather than “the right job.” What do you think?

I like your turn of phrase! The reason is that there are many opportunities for professionals to fit in to startups. But, by and large, they don’t know how to begin. The paths are opaque and the career trajectories informal. Therefore, finding the right fit and learning how to excel in that capacity is indeed the key.

For those thinking about launching a startup or joining one, any advice?

There are three stages to a startup. First, the jungle, when things are super-early and chaotic and the startup is pre product market fit. Startups in the jungle are typically 1-50 employees and running experiments regarding the fundamental customer value proposition, the best go to market and the business model.

Second, the dirt road, when things are more clearly defined but still bumpy and twisty. During the dirt road, the initial product-market fit is achieved and the company is more focused on scaling experiments. These scaling experiments are focused on the team and organization structure, sales and marketing approach (searching for a repeatable, scalable model) and further business model experiments that converge to more profitable unit economics (which are of little concern in the jungle). Dirt road companies tend to be 50-500 employees.

The final stage of a startup is the highway, when things are very clearly defined and it’s a race to the finish. Highway stage companies are greater than 500 employees and focused on building out a scalable, repeatable operating machine.
Picking the right stage fit for you is a personal preference based on risk tolerance and the kind of environment you find most fulfilling.

You observe: “I find that people who work at startups are categorically happier with their jobs and with their careers than people who don’t. Startups provide a greater degree of freedom and autonomy.” (Page 214)

Author Daniel Pink (Drive) and Harvard Business School professor Theresa Amabile (Progress Principle) have both extensively researched the fact that employees (and people in general) are happier when they have a sense of purpose, meaningful relationships and autonomy. Startups provide all of these elements in spades.

Of all that you have learned throughout your life and work thus far, what is the one lesson that has proven to be of greatest value to your personal growth and professional development?

Focus on your base. For me, my base is my relationships with my wife, my children, my siblings, and my parents as well as my health. As long as my most dear relationships and my health are strong, I can achieve anything.

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Jeff cordially invites you to check out the resources at these websites:

Link to his website

His Amazon link

His YouTube videos link

Jeff’s blog link

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