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So, You Want to Join a Startup

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Jeff Bussgang, a venture capitalist who teaches entrepreneurship at Harvard Business School, knows from personal experience and having funded many startups that there’s more than one way into that world. You don’t have to have a technical background. Excellent communication skills and a high emotional IQ are startup skills, too. Bussgang, the author of Entering StartUpLand, walks through the process of finding your dream job in a new company.

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CURT NICKISCH: Welcome to the HBR IdeaCast from Harvard Business Review. I’m Curt Nickisch, in for Sarah Green Carmichael.

One way to see how the economy is changing is to go to a city’s commercial district and see who’s there. One hundred years ago, this spot in downtown Boston was home to leather manufacturers. Ten years ago, financial institutions. And those are still here. But today, the asset manager Fidelity is just blocks away from startup incubators and coworking spaces. You’re just as likely to bump into a banker as you are a coder. Deborah Heines works at a startup here.

DEBORAH HEINES: We manufacture and import goods from China, and it’s solely an ecommerce play.

CURT NICKISCH: Heines used to work at a 150-year-old insurance firm nearby. She left the corporate world to be part of a small team and own some equity in her company.

DEBORAH HEINES: There’s real value to being passionate about what you’re doing and to feel like you’re contributing and actually making a difference or moving the ball forward in a big way.

CURT NICKISCH: Another corporate transfer here is Tim Lozeau. Do you work down here?

TIM LOZEAU: I just started today.

CURT NICKISCH: You did?

TIM LOZEAU: Yeah!

CURT NICKISCH: Lozeau used to work for an established advertising agency. Now he’s selling a software product he’s still trying to understand, but he feels good about the move.

TIM LOZEAU: It’s sales. You’re talking to people.

CURT NICKISCH: To him, moving to a startup didn’t feel risky. He did his homework about the industry, and the people behind the venture.

TIM LOZEAU: I think that really lessened any kind of nerves I had about going to a startup. Whereas, if people are going in a little more blind or maybe less educated on the company, the background, the direction they’re going, yeah, it could be a lot more nerve-wracking.

CURT NICKISCH: And our guest today hopes more people will discover they can build a career in startups.
Jeff Bussgang is a venture capitalist who teaches entrepreneurship at Harvard Business School. He’s written a new book with practical advice about how to get into a fast-growing venture without founding one. It’s called Entering StartUpLand.
Jeff, thanks so much for coming on the show.

JEFF BUSSGANG: Pleasure. Great to be here.

CURT NICKISCH: So, what is StartUpLand to you?

JEFF BUSSGANG: It’s a place where you can join a company that is on a mission. And it’s a company that’s young, that’s vibrant, that’s growing, that’s innovative, and bands together a group of people who are on a particular mission. Some people are intimidated about being a joiner. But there are thousands and thousands of joiners for every one founder. What I try to do is demystify and deconstruct the startup in order to help joiners find their way in.

CURT NICKISCH: Now, you had this path yourself to some extent, right?

JEFF BUSSGANG: Very much so. I was a joiner. My first job out of business school, I joined a 30-person Series A startup called Open Market, which was trying to turn the internet into a secure business environment back in the mid-90s. And I had an amazing five-year run there, through an IPO, through tremendous growth, many ups and downs, and that I think taught me the magic of being a joiner.

CURT NICKISCH: You started business school after being a consultant for a while though, too, right, at Boston Consulting Group. Did any of your former colleagues at BCG say, you must be crazy?

JEFF BUSSGANG: Yeah, I actually remember, one senior partner, when I told him that I was going to join a startup, he said to me, You know, Jeff, at startups there are very, very few people that have any decision-making power. You’re making a huge mistake because you’re going to find it incredibly boring. You’re not going to get any interesting responsibilities; you won’t make any interesting decisions; you’re just going to be very tactical.
And, you know, I laugh now in retrospect—he was completely wrong. And anybody who’s been a joiner at a fast-growing startup knows how completely wrong that advice is. When these startups are growing, they desperately need people to step up and take leadership. And that’s part of the fun because you could be in your mid-20s and have no right to be a vice president of product management or marketing, which is what I was in this company in my mid-20s, and yet suddenly you’re thrust into the into the role because there’s no one else available, and you’re moving so fast you don’t have the time to stop and take a breath. And that’s, I think, the magic of StartUpLand for young professionals and mid-career professionals as well. You get pushed and stretched in ways that really force you to grow and learn and adapt in an accelerated pace.

CURT NICKISCH: You teach this Launching Technology Ventures class at Harvard Business School. It’s for MBAs. A lot of students have heard the lore but aren’t natural innovators or founders maybe, right?

JEFF BUSSGANG: Yeah. The founder is a very special animal. A founder is someone who has an idea, who is brilliant, creative, visionary, irrational, risk taker. Not everyone sees themselves as founders, but they know they want the allure and the benefits of StartUpLand, and so they become joiners.
The other thing I would say is a lot of young professionals early in their career are very risk averse. They work all their lives to get into the best possible college. They try to find the best possible job that will set their careers up in the best possible direction, and they view startups to be risky. They view startups to be perhaps non-obvious places to build a long career, but rather a risk of being a flash that comes and goes.
And so, one of the things I also try to do is give people a way to learn about startups and to build the skills that will carry them beyond the individual startup but really help them in building their careers.

CURT NICKISCH: They’re right that startups are risky though.

JEFF BUSSGANG: Yes, startups are risky. Individual startups are risky. But building a career in StartUpLand may not be very risky at all because you’re building a set of skills and a set of capabilities, and you’re building a network that you can carry with you for decades. The working world is changing dramatically, and the career path of decades in one individual company, that’s over; that’s gone.
And what is happening now over a 50-year working cycle is that people are going to be changing jobs every three years, every five years. That means they’re going to be in 10, 15, 20 companies over their lifetime. And so, what you want to do is you want to find a way to get into StartUpLand, enter into that universe, and put yourself in a position to develop an amazing career there, and find a handful of great companies in that portfolio of 10 to 15 companies that you may work for.

CURT NICKISCH: If you’re trying to build a career that way, it sounds like joining startups may be easier than founding startups.

JEFF BUSSGANG: I hate seeing people confuse entering into StartUpLand with becoming a founder. If you want to get into that system, you can do it just as easily by jumping onto someone else’s idea and following someone else’s blazing path. And that’s what the joiners do.
They come in as employee No. 10. They end up being the first business person or maybe the first marketer or the first salesperson in a startup. Maybe they come in pre-product market fit. Maybe they come and post-product market fit and help the company scale. Whatever stage they enter into, they’re a part of the journey. And I think that can be incredibly fulfilling and enriching, and as I said, can lead to building a career where you develop these capabilities about how to succeed in a startup, how to scale a startup, how to navigate through the search and discovery phase that every startup goes through. And I think that’s the that’s the new career path for many professionals in our world not just in our country.

CURT NICKISCH: What’s the hardest part about getting into a startup?

JEFF BUSSGANG: I think the hardest part about getting into a startup is figuring out where to begin and what job there is to be done. So, I’ll have people come to me and say, Hey, I want to join a startup. I’m very strategic. I’m very operational. And I say to them, Well, that’s not really helpful for a startup. What a startup needs is somebody who can do a very particular thing can you sell can you build a product and you market. Can you help do the finance function you need to have a particular skill to be helpful to a startup. And so, one of the challenges for young professionals who haven’t yet developed those functional skills is what skills do I want to pick. It’s not just joining a startup or joining a startup to do what got it.

CURT NICKISCH: It’s also a question of what space to be in, too.

JEFF BUSSGANG: Yeah, startup selection is really hard. Look, it’s easy if you want to be on Wall Street to figure out who the top five banks are on Wall Street. It’s easy if you want to be in a consulting firm to figure out who the top five management consulting firms are. But if someone says to you, I want to go join a startup, you know, how do you have the conversation: Well, what’s the best startup for you?
And that’s one of the things I try to do in the book is to share a rubric that I’ve developed over the years that helps people think through how to select from the thousands and thousands of startups that are out there, how to develop a set of criteria to narrow it down to a cohort of startups that may be most interesting to them.

CURT NICKISCH: Let’s pretend I want to join a startup, and I come to you and I say, Jeff, help me break into the space. Let’s try this.

JEFF BUSSGANG: Let’s do it. So, first thing I ask people is, what are you passionate about? So, what domains do you have the most passion about when you read blogs or read the newspaper—I call it the Wall Street Journal test. When you open up the Wall Street Journal, what are the articles that you’re attracted to? And so, we would have a conversation about, what are you passionate are you passionate about. The revolution that’s happening in the media industry? Since you have a lot of experience in media, that might be a natural area. Are you passionate about the future of retail? Are you passionate about blockchain? So, what are the things that you’re finding in your free time or in your spare cycles you’re thinking about, reading about? What lights you up?

CURT NICKISCH: I mean, I definitely, you know, like the B section in the Journal. I’m very interested in like how work is going to change what we’re going to do in the future is a lot more computers and machines take over stuff that’s actually kind of boring to do and give us more time.

JEFF BUSSGANG: Perfect. So, that’s a future of work maybe an area of inspiration for you. Yeah. And future of work, turns out there are a ton of startups that are operating in the future of work. And so, I would dig in now to the next question. Once you’ve picked a domain, then I say pick a stage. How risk averse are you?
Are you interested in joining a really small team—three-person, five-person team—or would you rather walk into a 500-person company that already has a lot figured out and feels a little bit more structured where you could plug in into the system more easily?
And so, I characterize three stages of a startup. The jungle, the dirt road, and the highway. In the jungle, you’re hacking around without a clear direction. On the dirt road, that direction is clear, but it’s bumpy and windy. And on the highway, it’s pretty smooth and operational, and it’s all about speed.
So, the question I ask people I talk to is, are you a dirt road person, a highway person, a jungle person? What’s the best fit for you in terms of stage?

CURT NICKISCH: I think I think dirt road sounds like the most fun to me.

JEFF BUSSGANG: Great. So, dirt road companies, and the employee count 50 to 500, and so now you’re looking for companies that are doing things in the future of workspace that are 50 to 500 employees. And then the third thing I ask is, pick a city. And this is one of the trickier and more subtle pieces of advice. For young professionals who feel like they are able to have a lot of flexibility, I tell them pick a city where you can see living the next 20 or 30 years. Because StartUpLand tends to be very community centric. The Boston community, the New York community, the Seattle community, Silicon Valley—they’re all very different, tightly bound communities. And once you learn about and build a network in a community, it leads naturally to the next company.
One of the tests I like to recommend folks who asked me about whether this particular company is a good place to join is I asked them, could you see yourself working with that founding team in their next company if this one fails or even if it succeeds? Because one opportunity often leads to another. And so, because StartUpLand is so community centric, I asked people to really think deeply about picking a city.

CURT NICKISCH: Yeah that’s easy for me because I’m here in Boston. But what about for somebody who’s in Kansas City or in Bavaria or in Perth?

JEFF BUSSGANG: Look, there are probably 10 fantastic startup communities in the world: four or five in the U.S., Tel Aviv, Berlin, London. And if you’re not in one of those 10 cities, and you don’t have the flexibility to move, it can be tricky.

CURT NICKISCH: What do you tell people who feel like they’re on the outside of this world?

JEFF BUSSGANG: I think for people who are on the outside, they have to do one of two things. They have to broaden their definition of what a startup community looks like. So, you know, I’ve invested in a company in Boise, Idaho. Now, Boise, Idaho, does not have the most vibrant startup community relative to, say, Silicon Valley or Boston, but there are a bunch of startups in Boise Idaho and a bunch of people who care about startups in Boise Idaho. So, there may be a microcosm of the ecosystem that you can be a part of it you can even start and even help nurture. You could create a meetup in your community for startups and startup-interested executives and founders and joiners.
Then the second thing you have to do is you have to hustle to establish relationships. I know an entrepreneur who is in Kentucky and built his company and came up with his idea and just hustled online to build relationships over social media with entrepreneurs in Silicon Valley and in Boston. And when it came time to raise his angel round, he was able to raise money from entrepreneurs in those geographies because he had reached out and been proactive and been a hustler in establishing those relationships.
But back to you and your criteria. So, if you want to be in Boston be a dirt road company and do something in the future of work, well, now you’ve got your criteria, and now you can go around to all the people you know and StartUpLand. You can go around to gatekeepers like lawyers and venture capitalists you can go to various CEOs of companies that you may know are founders and tell them about your criteria and ask them, what’s the what are the best companies; name the three best companies in that area; who are the companies that are inspiring. And then you’ve got to figure out what are the jobs to be done and what is a fit for you.

CURT NICKISCH: What functions do you think are the most needed in startups?

JEFF BUSSGANG: There are a few really interesting areas that have emerged that have become incredibly important to the success of startups, and one of them is around the building of a community around your company. And so, this new role has been created called community manager. And what does it take to build the community? It takes excellent communication skills, relationship skills, emotional IQ, an ability to reach out across cultures and get along with people and communicate effectively with people that are from diverse cultures because it’s a global community.
In fact, I don’t talk at all about engineering in the book. The deconstruction of the startup organization is all about the jobs that can be done that are the non-technical jobs, because the majority of the jobs in a startup are non-technical.
One of the examples of that is product management. There is a theme in some places that you have to be deeply technical to be an effective product manager. In my experience, the best product managers are liberal arts majors; because if you think about what the skills are for product management, it’s communication skills, analytical skills, it’s leadership skills.
One of the big issues of gender diversity which we have in StartUpLand—and it’s a very troublesome issue, and on many dimensions, not enough companies have balanced gender workforces—is that many women are intimidated by StartUpLand because they think, Well, I’m not an engineer. And only 20 percent of engineering graduates are women in the U.S., in the United States. I’m not an engineer, so it’s not for me. And I think that’s a complete fallacy. And one thing things I try to teach my students is how to be fantastic product managers and how to be fantastic contributors to StartUpLand, even if you don’t have a technical degree.

CURT NICKISCH: What functions do you think are the most needed in startups?

JEFF BUSSGANG: There are a few really interesting areas that have emerged that have become incredibly important to the success of startups, and one of them is around the building of a community around your company. And so, this new role has been created called community manager. And what does it take to build the community? It takes excellent communication skills, relationship skills, emotional IQ, an ability to reach out across cultures and get along with people and communicate effectively with people that are from diverse cultures because it’s a global community.
In fact, I don’t talk at all about engineering in the book. The deconstruction of the startup organization is all about the jobs that can be done that are the non-technical jobs, because the majority of the jobs in a startup are non-technical.
One of the examples of that is product management. There is a theme in some places that you have to be deeply technical to be an effective product manager. In my experience, the best product managers are liberal arts majors; because if you think about what the skills are for product management, it’s communication skills, analytical skills, it’s leadership skills. Those are all the skills that are required and you learn in a liberal arts environment. Those are not skills that you learn when you’re learning C++ or Ruby on Rails.
One of the big issues of gender diversity which we have in StartUpLand, and it’s a very troublesome issue and on many dimensions, not enough companies have balanced gender workforces is that many women are intimidated by StartUpLand because they think, Well, I’m not an engineer. And only 20 percent of engineering graduates are women in the U.S., in the United States. I’m not an engineer, so it’s not for me. And I think that’s a complete fallacy. And one thing things I try to teach my students is how to be fantastic product managers and how to be fantastic contributors to StartUpLand, even if you don’t have a technical degree.

CURT NICKISCH: What functions do you think are the most needed in startups?

JEFF BUSSGANG: There are a few really interesting areas that have emerged that have become incredibly important to the success of startups, and one of them is around the building of a community around your company. And so, this new role has been created called community manager. And what does it take to build the community? It takes excellent communication skills, relationship skills, emotional IQ, an ability to reach out across cultures and get along with people and communicate effectively with people that are from diverse cultures because it’s a global community.
In fact, I don’t talk at all about engineering in the book. The deconstruction of the startup organization is all about the jobs that can be done that are the non-technical jobs, because the majority of the jobs in a startup are non-technical.
One of the examples of that is product management. There is a theme in some places that you have to be deeply technical to be an effective product manager. In my experience, the best product managers are liberal arts majors; because if you think about what the skills are for product management, it’s communication skills, analytical skills, it’s leadership skills. Those are all the skills that are required and you learn in a liberal arts environment. Those are not skills that you learn when you’re learning C++ or Ruby on Rails.
One of the big issues of gender diversity which we have in StartUpLand, and it’s a very troublesome issue and on many dimensions, not enough companies have balanced gender workforces is that many women are intimidated by StartUpLand because they think, Well, I’m not an engineer. And only 20 percent of engineering graduates are women in the U.S., in the United States. I’m not an engineer, so it’s not for me. And I think that’s a complete fallacy. And one thing things I try to teach my students is how to be fantastic product managers and how to be fantastic contributors to StartUpLand, even if you don’t have a technical degree.
So, in your case, you’re more likely to be on the business side or the marketing side because that’s your experience. You’re not a software developer, and you’re probably not a sales person, and so you’ve got to think about do I want a job and product management or in marketing. Well, where in marketing are you a fit? Is it inbound marketing, or is it marketing communications PR? Is it more product marketing is a channel marketing? You have to pick a particular functional area.
I think one of the things that people get confused about is they see startup organizations as these amorphous blobs. But in truth startup organizations look just like big organizations. From a functional standpoint, it’s just there’s more dynamism under the surface, but there is still a sales function, a marketing function, a finance function—

CURT NICKISCH: An org chart.

JEFF BUSSGANG: An org chart. It just happens that the org chart changes every three months and that you may be a marketing manager one day, and you may be asked to go help the CFO do a model on the arm of a certain marketing campaign, and suddenly you find yourself in the finance department for the next three months. So, there’s a lot more dynamism to it but those functions do exist.
So, you as an aspiring joiner, after you pick a domain, after you pick a stage, after you pick a geography, you need to pick what the job is that you’re actually going to do and then, you need to go to those startups and offer—what I call come bearing gifts. You need to come and show them that you’re there to add value. You’re not just there to take value from them.

CURT NICKISCH: Coming up, we’re going to talk about the money. The financial considerations that come into play when you leave big companies for new ventures. But first, we’re going to look at the startup boot camps that are trying to help people make this transition. Jeff writes about them in his book. So, we went to one.
[Audience cheers and claps]
It’s graduation day at Boston’s Startup Institute. Nacole Buyck is standing in front of an audience of hiring managers, giving an elevator pitch—about herself.

NACOLE BUYCK: Career pivoting is like a pageant.

CURT NICKISCH: Buyck used to compete in beauty pageants. But now she’s competing for a startup job.

NACOLE BUYCK: I want a position in a high-energy firm, where I can be creative, leverage my analytical and communications skills. Oh—I also want world peace.
[Audience cheers and claps]

CURT NICKISCH: After Buyck and her fellow graduates finish their pitches, they go to a reception and mingle with those startup hiring managers who were in the audience. One grad, Raela Ripaldi, has already accepted a job offer at a digital marketing startup.

RAELA RIPALDI: So, I’m going to be brutally honest. Like, before this, I pretty much thought I wanted to move to the Bahamas and be a bartender, like, with my dog on the beach. I was kind of done with corporate America. And about halfway through I was like, No! I like working. I like tackling problems. And so, it really just changed my perspective and brought back a lot of confidence that I had lost. And that to me is really priceless.

CURT NICKISCH: Ripaldi spent $7,000 to go through this eight-week program. And she found a startup job. So, I asked our guest today, Jeff Bussgang, are these startup boot camps worth it?

JEFF BUSSGANG: Like any educational institution, there’s going to be a variety of quality to these startup boot camps. But I think the good ones are excellent. I think they represent transformational opportunities much in the same way that going back to school represents a transformational opportunity for young people. Or mid-career people who do their executive MBAs and whatnot.
One of things that the boot camps do really effectively, in addition to helping you with some of the skills and some of the cultural differences between big companies and startups, is they help you with the network. The good boot camps at the end of the program expose you to fast-growing startups that are growth-stage companies that are hiring and that are open to hiring people like you. And there is an alumni network, again like a good university, of people who graduated from the boot camp a year ago, two years ago, three years ago, who you can leverage as part of your networking.
So much of this is about creating community and finding a way into the community. To enter into that world just requires an investment in time of reading the right things, in relationship building, and networking your way in, and finding a place where you can contribute and add some value. That’s what I think what is so magical about StartUpLand is that it is such an interesting community that you can plug into and that’s very welcoming of outsiders if the outsiders take the right steps to enter in in the right way.

CURT NICKSICH: What if outsiders are older? StartUpLand, I mean, we joke about table tennis, foosball, and free food. But those places can seem intimidating because they just seem so young.

JEFF BUSSGANG: Well, first of all, when you talk about the future of work, we have an aging workforce in America and 50-somethings and 60-somethings and 70-somethings who are going to continue to be vibrant, powerful workers in our workforce. We need to find a way to get them into StartUpLand and get them to be comfortable and productive in StartUpLand.
The second observation I would make is that those individuals have a lot to contribute because they’ve developed functional expertise. In the finance function, for example, it’s very hard to take somebody right out of college and have them be a productive vice president of finance. They don’t know accounting principles. They don’t know how to close the books. They don’t know how to balance the balance sheet. They don’t know how to deal with debt. And I know this a little bit from experience that you need to have experienced, savvy, sophisticated individuals in the finance function. And so, there are many areas where I think middle career—even people who are late in their career—can be incredibly valuable at startups.
So, I think at any age you can contribute. I think what many senior folks need to do is they just need to meet people where they are. They need to be a little bit better at taking it to the level of the startup and really taking the time to learn what does the product do. What does the company do? What’s the technology that’s underlying this? So that they really, instead of telling old stories about the last technology wave, they’re really in the weeds and the current technology wave.
In fact, what’s amazing is a lot of our young founders in our portfolio, as well as the young joiners, they all need coaches. I mean, if I could have a great coach with 20 or 30 years of experience for every executive or mid-level manager at one of my startups, would be amazing. I think one of the tragedies right now in StartUpLand is that middle management is not only being decimated because of the flattening of these organizations, and there are pros and cons to that, but the con is that there is a complete lack of training and coaching going on in these companies.

CURT NICKISCH: You broke down how much people get paid or can get can expect to get paid at some of these different stages and in some of these different roles. What do you how what do you tell people about the money in StartUpLand and how to think about it?

JEFF BUSSGANG: I tell people, look: think about your risk tolerance. Think about the tradeoff between equity upside and cash. And think about what stage you want to enter into and pick a spot that you’re comfortable with for the next few years and also pick a spot knowing that the equity is very risky that there are only a few of these lottery tickets that you can cash in for millions of dollars. It happens and those are the stories that everybody loves to talk about the Amazon millionaires and the Uber millionaires someday if and when Uber goes public.
But it’s the you know many, many people that had the wealth on paper and then saw the dreams crash that you also hear about that gets people nervous and scared of startup plans. That’s why I think you’ve really got to focus on risk tolerance and pick the package that’s right for you.

CURT NICKISCH: I also saw an interview with somebody who went to work for Apple early on with Steve Jobs somebody who had a lot of experience and was I think it was in marketing and was offered a job and Steve Jobs said, Look, we just we don’t have a lot of cash. We want to give you this package with equity, and he said, Like a fool, I held out for the money.

JEFF BUSSGANG: Yeah. So, look: it’s a little bit trickier to select and negotiate your compensation in StartUpLand. And you have to be even more sophisticated about what are stock options and what is the preference stack that sits on top of the common stock that you’re receiving an option to buy, and what is the vesting schedule, and what does acceleration and cliffs, and all sorts of other things. I try to give a little bit of that in the book to help people navigate through.

CURT NICKISCH: Is there a sequel called Exiting StartUpLand?
JEFF BUSSGANG: I can’t tell you what the sequel looks like; but I know when I see a pattern, I’ll formulate something around it.

CURT NICKISCH: Jeff thanks so much for talking with the HBR IdeaCast.

JEFF BUSSGANG: Thank you.

CURT NICKISCH: That’s Jeff Bussgang. He’s a general partner at the early-stage venture capital firm Flybridge. He also teaches entrepreneurial management at Harvard Business School. And he’s the author of Entering StartUpLand: An Essential Guide to Finding the Right Job. You can find the book at HBR.org.
Thanks for listening to the HBR IdeaCast. I’m Curt Nickisch.



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