Chapter 2
Pick the Right Start‐Up for You
Don't worry about failure. You only have to be right once.
—Drew Houston, co‐founder and CEO of Dropbox
Are you chomping at the bit, ready to bolt from a corporate desk to the start‐up track? I was, too, when, soon after graduating, I signed up at my first start‐up. I rushed into the first opportunity that presented itself. This was a mistake. I knew next to nothing about the company—I didn't know about its funding, growth plans, or marketing plans. I didn't even really know what we sold. I knew the name, of course, but the product was some sort of specialized technology and I only had a fuzzy idea of what it actually did.
Ultimately, the company was successful. It had smart people at the helm, a strong product, and a compelling story. In many ways, it's the luckiest I've been in my career. Because in my haste, I made every possible mistake I could have made. And even though the company ended up being a success, we experienced long periods of struggle where we had to lay off swaths of the sales team, and it looked like the whole thing might fold. Which happens far too often.
At a dinner party a few years ago, I met a man who told me he worked an eight‐to‐five job for a big company in Austin. I asked him if he liked what he did, and he shrugged and said, “It's a job.” He volunteered to me that years earlier, he had gotten in on the ground floor of a start‐up and loved it, but it tanked after two years, and he never tried to work for a start‐up again. With the way I dove headfirst and blind into my first start‐up, I could have very easily ended up on a sinking ship, just like this guy. I didn't. I got lucky and picked a company that turned out to be a winner, and I ended up a millionaire. But you don't have to rely on luck.
What I didn't realize at the time was that, with the proper preparation and research, you can avoid this sort of precariousness. In this chapter, I provide strategies for finding start‐up job opportunities, and guidelines for how to choose the start‐up to join that will maximize your chances of success.
How to Find Start‐Up Opportunities
As you begin your search, you should keep this in mind—generally speaking, a start‐up handles hiring in two waves: in the first, they're just trying to assemble the core team. The start‐up usually is brand new, and as such, the process might not be as efficient. Once the start‐up is beginning to prove it is viable and can scale, then it makes second‐wave hires. These positions tend to be more specialized, the hiring process is streamlined, and the company already has a bit of momentum.
Recognizing the difference between first‐ and second‐wave hiring will help you evaluate each start‐up you find to determine whether you want to apply, as there are advantages and drawbacks to joining with each wave. If you join in the first wave, the company will be smaller and in a more precarious position, as they haven't proven viability. For the most part, these jobs are hard to find, and usually go to someone with either a personal connection to the founder or some sort of a reputation in the start‐up world. For that reason, combined with the precariousness of joining a company in the first wave, I recommend that young workers or people looking to make their transition into the start‐up world go after second‐wave positions.
Research Posted Jobs Online
I know, you just rolled your eyes and muttered “obviously.” This is still the best place to start, but to get results, you've got to know how to look. Start by deciding which area of technology most interests you (e.g., cybersecurity, health information technology, artificial intelligence), then add which field or department you want to work in (e.g., finance, marketing), and finally add phrases like “start‐up” or “early stage start‐up.” Mix it up by beginning your search based on geographical location, whether that's where you live or in a city you're thinking of moving to. Then, look for positions where you can work remotely. Check LinkedIn and other job websites for postings by new companies. These early searches will yield a list of companies and jobs in your area, as well as entrepreneur events and trade fairs you can attend.
Explore Technology Accelerators
Accelerators (or seed accelerators) are application‐only programs that provide capital, mentorship, and educational opportunities to start‐ups, which often culminate in either a public pitch event or a demo day. These are a great weeding‐out tool, as companies that go through an accelerator have a greater chance of attracting a lot of venture funding. Research local accelerators and see which companies are participating.
Attend In‐Person Entrepreneur Events
These events might take the form of trade shows, seminars, talks given by industry leaders, or networking events held by local trade groups, among many others. For example, in cybersecurity, the SANS Institute is a cooperative research and education group. SANS, true to its mission, hosts a large number of training and networking events around the country, many of which are open to the public and could provide useful contacts for breaking into the cybersecurity field. Once you know which field of tech you want to work in, figure out what the major trade groups are (like the SANS Institute) and be on the lookout for upcoming events. Most local accelerators post calendars on their websites that list industry events in the area.
When you have selected a list of events to attend, go to them. But don't just show up. Go with a plan. Research the event beforehand, know who will be there, and know who you want to talk to. When you arrive with your target list in mind, don't just cruise around asking CEOs for jobs. Introduce yourself and ask questions. People love to talk about themselves, so this is the easiest way to establish rapport. You can start by asking about the technology at hand, but eventually you should personalize it. Ask them about things like what they do for the company, what they love about working for the company, what makes the company special, and what makes them excited to get up in the morning.
Listen to their responses. Don't just feign interest. This is the most important thing—nobody likes insincerity and people can always detect it. If you're serious about breaking into whatever the industry is, you should have a genuine interest in the answers. Because you will learn, not only about the company, but also about how to be successful in the industry. Then, once you get a conversation flowing, if a bridge to asking about employment or getting your foot in the door materializes, you can use it. You can say something like, “Wow, it sounds like you have the kind of position that I would really love to have one day. Do you mind if I tell you what I do, where I'm at, and would you mind giving me some pointers?” Then, without having seen your resume, they already have a sense of your skill set. From there, you can ask if they know if their company is hiring, and if you could throw your hat into the ring. This way you don't come across as desperate, just genuinely interested in the company's work.
If you go in with the mind‐set of selling them on hiring you, then you're going to get nowhere. People hate to be sold to. They want to give and get. When it comes to networking, the best way to sell them on you, is to focus on them.
Engage with Start‐Up Leaders Online
When you find the companies you're interested in, follow them and their leaders on social media. Read their posts, and when you see something interesting or that you have questions about, reach out. A way this might work is if you read a post of theirs on LinkedIn, and it resonated with you. You could then reach out with a well‐written, specialized, private connection request in response to the post. This will show that you have done your homework, have thought about the industry and this person's role in it, and you want to engage in a serious manner. Again, you don't want to come across as someone just trying to get something or sell them on you.
If there is somebody you want to get in touch with, keep an eye out for their next speaking engagements, hiring events, or announcements about their participation in trade shows or conferences. Go to them, introduce yourself, and ask a couple of questions. With a little research, usually you can uncover their email address and send a thoughtful, well‐written email.
Of course, it's important to remember that you're reaching out to busy people who probably receive a lot of messages like this. Don't get discouraged if you don't receive a ton of responses—I know that I ignore most of the LinkedIn messages that I receive. But you can maximize your chances by preparing a well‐written, articulate, and diligent inquiry.
Attend Hiring Parties
When I worked for PentaSafe, we ran our headquarters out of a beautiful, redbrick Southern‐style mansion. People had their offices in bedrooms, bathrooms, and closets. It, of course, seemed like the perfect place for a party, and at that time we were growing rapidly and needed to hire more team members.
More than once, we got a few kegs and put them out on the front lawn, then just spread the word around. At the time, a much larger competitor was headquartered nearby, so we hired a banner plane to fly over their headquarters with a sign that said “We're Hiring! Check out our website for details about our hiring party!”
People would come, have a few drinks on the lawn of the mansion with us, listen to music, and talk about the company. Several start‐ups still use tactics like these to attract talent, and if you have a chance to attend one of these parties, seize it! Not only are they great for getting you hired, but they also will give you an excellent opportunity to gauge the company culture.
Be Willing to Intern (Preferably for Pay)
If your resume doesn't include any experience beyond front‐line retail or foodservice, it won't garner a lot of attention, even at a start‐up. That's why, if you're in school or fresh out, an internship is a great way to get your foot in the door.
The start‐ups I worked for frequently hired paid interns in both tech and nontech positions. One start‐up, The Planet, hired a young man as a finance intern while he was a junior in college. Since he had no experience in finance, we would never have hired him as a full‐time employee, but we were willing to give him a paid internship to assist our finance leader. With us, he made meaningful contributions to our financial analysis efforts and developed his Microsoft SQL skills at the same time. This is important—not all internships are created equal, and if you're about to provide free or cheap labor for an organization, it's vital that you get valuable experience in turn. Make sure to ask what the scope of any potential internship will be, and don't be afraid to advocate for yourself as an intern. Remain professional, of course, but remember that nobody will make sure that you benefit from your internship if you're not proactive.
Returning to the example, a year later, another start‐up offered that same student an internship where he could acquire a deeper level of experience, and he took it. Using what he learned from these two positions, he landed a good job in finance soon after he graduated. And, if he hadn't gone to work for them, we would have hired him back in a heartbeat.
This is not an unusual story. Internships give you the chance to work in different areas, prove yourself, and develop relationships with managers so you have a head start when you want to break into the start‐up world.
To score an internship, research companies and reach out to specific people, describe why you're interested in an internship, and offer your talents. Usually, if you show initiative and a genuine interest in the company and the work, people tend to be receptive.
Seek Mentors
In early 2019, I received an email from a Harvard undergrad. It said, in short, “I'm interested in tech and cybersecurity, and I wonder if you can teach me some things to help me on my path ahead.” I'd never spoken to him before and he had discovered my email while researching tech start‐ups, but his message was well‐written and sincere. So I said yes. Executives, obviously, are busy, but they all remember the people who helped them achieve the success they have, and most are on the lookout for opportunities to help the next generation. If an executive sees a potential fit or mutual benefit, they'll make the time to help. I met with the young man a couple of times for mentor‐mentee‐type discussions. If he ever asked me for an internship, I'd say yes, because I already know him. And once I see how he works, he would be in a plumb position to be hired as well.
With the glut of start‐ups in the market, after even a little bit of research, you can have a massive list of firms to choose from. So, time to start sending out resumes, right? Not yet. Next comes the most important step to ensure your success—evaluating the companies so that you pick a winner.
Five Criteria to Choose a Start‐Up
Yes, there are lots of start‐ups, and yes, they all desperately need talent, but exercise caution when selecting where to work. Not all start‐ups are created equal; a great one can rocket you into a successful future, and a dud can set you back, at least temporarily. Only the strongest start‐ups survive—current calculations show that about 75% of all venture‐backed start‐ups fail.1 I know what you're probably thinking, but don't be daunted. Instead, be savvy enough to pick a winner. Approach the decision like an investor would, because going to work for a start‐up means you will be investing your time, energy, and talent. And through stock options, you may even get company equity. As an investor, find out enough to be sure the company you go to work for is the right fit.
Not only will you want to pick a winner as your first start‐up, but also be ready to find a new one. The time will come when you're rocking it with one start‐up, and suddenly the leaders announce a successful exit. This can be great—if you have stock options, their worth will soar—but just as suddenly, you're out of the job. Always have a bit of a head start on a backup plan so you're better positioned to leap over to a new start‐up if need be.
Then, on the flip side, the company might fold and you might end up in the same situation of the person I met at that party, suddenly out of the job and tempted to go back to the steady corporate life. That's what you want to avoid—in the volatile world of start‐ups, the company you work for might suddenly cease to exist. It's a reality, but one that you can plan for and ensure that you still can go on to have a successful career in start‐ups.
So, what should you look for? First and foremost, the start‐up must have a good story. The story should describe its mission in the context of the lives of its customers and how it solves a problem, and why it was launched in the first place. But a compelling story is not enough. You want it to have a good story as well as strong indicators for success. If you find a start‐up with both, you will likely get the outcomes you desire personally, professionally, and financially.
Here are the five criteria to look for to find the best start‐up fit for you, and one that's likely to succeed as well.
Quality People Who Share Your Values
Doug Erwin, a venture capitalist who evaluated 8,000 companies to find the 14 that he chose to invest in, says, “The first thing that a VC invests in is the management team. The second thing is the management team. The third thing is, you guessed it, the management team.” He continued, “The right leaders can turn a shitty product into a success, but poor leaders can't save an exceptional product. The people are the most important.”
I agree one hundred percent.
Before you apply for a job with any start‐up, look at the company's values and mission statement. Make sure they align with the values that are important to you. This should give you an early idea about the leadership and the culture. Then, when you get the chance to talk with people who work there, ask if they know the company's mission. Ideally, every employee in the boat knows the company mission and is rowing in the same direction.
After you read the values and mission statement, do your research on the head honcho and other key leaders. Seek to find a team of leaders you can respect, trust, and admire. Consider: has the CEO launched a business before? Was it successful? If so, chances are high that this leader can do it again, and it's likely he or she brought other key leaders along to this company. Most CEOs have great stories to tell, and they often include past failures. Pay attention to the CEOs' stories and how they overcame past challenges. See if their stories inspire you.
Check out interviews and blog posts from company leaders to learn about their backgrounds, goals, and their abilities to influence and inspire. Nothing enhances your odds of winning more than surrounding yourself with A‐plus talent, so choose a start‐up where you are inspired by those who can mentor you and help you become your best as you grow with the company.
Besides looking at the leadership team, get a feel for the company culture at all levels. You can tell a lot about the culture by observing what I call “the heartbeat” of the company. You can sense the heartbeat if you sit in the parking lot at 6:30 a.m. and watch what time people arrive, and how they look as they enter. Do they walk in with a pep in their step as they begin another day of important, exciting work? Or do they look drained as they plod across the lot and pull open the door that looks heavier than it possibly could be?
Once you get inside for an interview or meeting, use every moment and notice every detail to gauge the company's culture, from the demeanor of the first person who greets you; to the energy levels of the people coming and going; to the decor, postings, and office environment itself.
Also, use the interview or meeting to ask direct questions. Ask your interviewer about the CEO, what they love about their teams, and what they would be doing if they weren't building a start‐up right now. All of this will give you a better sense of the type of people this company attracts.
The Concept Fills a Big Market Need
Cool technology alone doesn't cut it. No one—not consumers and certainly not investors—spends money on “nice‐to‐have” technology; they spend money on the “need‐to‐haves.” If the company's product or service doesn't fill a genuine market need, then the ship's going down, and you'd be a fool to board it.
How can you tell if a start‐up's product or service fills a huge need in the marketplace? Sometimes it's fairly obvious. Back in 2013, a company sprouted up around a product called “Vessyl,” a cup that, in real time, told the users what was in it. Stephen Colbert picked up the story and quipped, “Finally, a way to get information that used to only be available on the can I poured the drink from.” The product filled no genuine market need—it was just nifty nonsense. Reading the website, they tried to make it sound incredible: a “revolution in drinking,” promising data in “real time.” In short, it was loaded with buzzwords. And, as of 2018, Mark One, the company behind Vessyl, is no longer operating.2 Not only is it a good lesson in how important need is to market value, but it's also a good rule of thumb—if the website contains more buzzwords than actual specifics about market need, it's probably best to steer clear of what they're selling.3
It's not always that easy, however. When you've perused the website and still aren't sure, research the company online and read what influencers have to say about its ability to provide a unique value that sets it apart from competitors. Find the company's growth plans online, and compare them to others in the marketplace. Look for evidence that the start‐up is sufficiently ambitious with a solid business strategy that includes managing future growth. See if you can find signs that the start‐up has every chance for success in what they offer and how they are structured. Again, you can get a strong sense of this during an interview. Ask questions about the product, the customers, and the market.
Good examples include: “Why is now the time for your company to exist? And why are you the ones to solve this problem? What's your biggest threat? What milestones have you achieved?” Ask them to tell you about a real paying customer, how they found the company, and the customer's experience. If they can't give a convincing answer to any of these questions, you should avoid that start‐up.
Finally, look for competition. Are there other companies working on a similar product? Is Google? Apple? Amazon? If so, good. This might seem counterintuitive, but competition means there's a market, and start‐ups can run nimble circles around big companies. You know who didn't have competitors? Vessyl, and we all know how that ended. Of course, you need to make sure that the start‐up you work for differentiates itself within the market, but there needs to be a market.
Besides a market to compete in, the product or service must have a competitive advantage. Kevin Klausmeyer, financial expert and independent start‐up board member, says the advantage can be found in a variety of areas, but the company must have at least one. “It could be product elegance, product features and functions, a unique partnership with a big player, or speed to market. When looking to join a company, make sure you understand the competitive advantage and how they plan to win.” He points out that both Tumblr and MeetUp were wildly successful tech start‐ups with their simple concepts (a blog platform and a social event platform) because they had the first‐to‐market advantage.4
A Great Product You Believe In
You want to work toward something you're passionate about. If not, why are you even in the start‐up world? You can complete rote tasks for any company, and many will pay you better for it than a start‐up. Before you apply, research a detailed description of the product or service the company offers, and see if it resonates with you. Do you believe in it? Would you purchase, use, or recommend it? I'm not saying that you have to be a target customer of the product or service, but I am saying you want to be proud of what you help to produce.
If possible, attend one of the company's shindigs in person, such as a marketing event, sponsorship activity, conference, or trade show. Pay attention to the reaction by the audience or other outsiders when they are presented with the spiel of the product or service. Talk with employees to get their insights about what the company offers. With a little time and energy, you'll be able to find out how well the product or service delivers on its core value proposition.
If you can't get behind the product with enthusiasm, move on.
A Role You Can Fill Today with More Opportunities Tomorrow
Look at the company's job postings and see if they have needs that truly match your interests and areas of expertise. Not all opportunities are posted, so a little networking can go a long way toward finding out what a company actually needs and how you can help. Don't settle for a role in which you have zero interest, but keep an open mind. Allow yourself the room to imagine what taking on new roles would be like. Be willing to be flexible in how you apply your skills. Remember, a lot of start‐ups haven't pigeonholed roles and responsibilities yet, and you need to be ready to step up when called upon.
Once you get to the interview stage, ask if the start‐up aims to hire people who they can develop and promote. Some start‐ups promote from within more than others. It depends on their culture and their leadership team's interest in and (usually brief) history of raising leaders through the ranks. Many times, I've seen promotions take place via a tap on the shoulder while someone is filling up a coffee mug in the kitchenette: “Hey, Courtney, I'd like you to step into the manager role, starting now.”
Choose a start‐up where you can make an instant impact, and grow into a larger role. It's best to choose a start‐up that's in it for the long‐haul and working to build a great company. If in the interview they're already talking about an exit, then that's your cue to exit the interview. What you're trying to do is find a strong enough start‐up where you can stay long enough to help build a great company with lots of happy customers and employees, while developing your own expertise and leadership skills along the way. If the interview discussion reveals that everyone is focused on selling out, rather than continuing to build the strongest possible company, then the selling day will never happen, so avoid wasting your time there.
The Start‐Up Is Well‐Funded
It all rides on the money, honey. Before you get too serious about pursuing a job with a particular start‐up, verify that the company is properly capitalized so it has the best chance at stability and growth. Choose a start‐up that has a long enough runway for it to get off the ground. That means there's enough money to go from development through marketing and launch and pay its people well along the way. This is not too much to ask; it's a non‐negotiable requirement.
Even if they offer stock options, you should never accept stock options in place of a livable salary, because if they're making that offer, it probably means they don't have enough money to launch, and those stock options won't be worth the paper they're printed on. A too‐short financial runway means the start‐up may run out of tarmac and, at best, putter out, at worst, crash and implode.
During an interview, ask questions such as, “How is the start‐up funded? What's the five‐year plan? How long is the runway? How tight is the budget right now?”
Find out where the money is coming from. Is it self‐funded or are venture capitalists behind it? Who has skin in this game? The answers to these questions will give you a good idea about not only the funding, but whether the leaders are inclined to tiptoe around the financials. If they lean toward vague answers, it would be hard to feel confident about their ability to be up front about the company's health in the future. Look for transparency and straight‐shooting conversations about financials. Also, VCs often list on their websites the companies they fund, so you can use this bit of research to confirm that a start‐up's funding is legit.
While funding is technically the start‐up's lifeblood and a concrete indicator of its chances for success, there is a bit of a chicken‐and‐egg scenario at play. If the management team is strong and the product solves a problem, then the funding will come. You're just usually better off to delay making a commitment until the funding is in place.
Those are the criteria I use to evaluate start‐ups. Only go to work for one that has a combination of all five. Three, even four, won't cut it. If you want to zoom to the C‐suite, you'll need an environment with these conditions to spur you forward.
Getting Hired
Finding companies to apply to and even get your foot in the door is only the first part—no matter what, there will be an interview process, and you have to nail it. Going into the interview, make sure that you're ready to demonstrate that you have the skills, and more importantly, the mind‐set that they are looking for. As I've mentioned, start‐ups place less emphasis on your education and prior experience than large corporations.
Doug Erwin, the serial tech entrepreneur I mentioned earlier in this chapter, says when he's hiring at a start‐up, “I look for people who want to build solutions to solve problems. People who have failed and then succeeded, and who aren't afraid to take chances. I look for people who are prepared. People who are good communicators and who have a sense of humor and can laugh at themselves. And, of course, people who have the skills to do the job. I want people who show they can think outside the box.”
What does this look like? Erwin tells the story about when he used to have a friendly annual meeting with the head of HR at Southwest Airlines. On one visit, Erwin waited in the lobby with a bunch of men interviewing to be pilots. Erwin says, “The lobby was full of these serious men with cropped hair, obviously military pilots. Someone came into the lobby and announced, ‘To all of you interviewing for pilot jobs, we are only interviewing people in shorts. Thank you very much,’ and then disappeared back through the door. I saw one guy cut his pant legs off right there in the lobby. Others ran out to their cars and put on their gym shorts, and came back in.”
While Southwest Airlines isn't a start‐up anymore, their HR team demonstrated a start‐up mentality in seeking quick‐thinking people who were willing to go all‐in and have a sense of humor. Bring that energy to your interview, and it will make you stand out to start‐up leaders.
Great energy will help, but the single fastest way to snag the attention of a start‐up founder is to have an elevator pitch—for yourself. This seems incredibly simple, yet most people don't do it. When you go into an interview, you need to be selling yourself, your brand, and what you will bring to the start‐up that nobody else will. For example, my elevator pitch for myself is, “I deliver plans for marketing strategy and execution that help start‐up companies achieve breakthrough revenue growth in brutally competitive marketplaces.”
One sentence that describes what they get when they hire me. And notice, it's not shy; it's bold and concrete. “Breakthrough revenue growth” operates well because it's vague (not a specific numeral), but clearly conveys that I will take revenue to the next level breakthrough. And notice brutally—I could have said very or hyper or extremely, but brutally tells you that I am somebody who's accustomed to working in fields where the competition can be cutthroat. You want to create your sentence so that when people hear it, they say: “Oh, how do you do that?” Once they ask, then you can follow it up with your story.
Of course, I have years of success to back this statement up. But this elevator pitch tactic holds up in all situations. No matter where you are, at any point in your career, you need to be able to succinctly express what makes you a unique asset. As an example, let's say that you're fresh out of college, looking to join a sales team, and you don't have much experience. Your statement might be, “I help companies I work for to increase sales by listening to customers and providing them the best solutions to solve their toughest business challenges.” Then, you tie it into who you are. You might not have much sales experience, but they'll ask, “How do you do that?” And you'll say, “I'm a hard worker and I learn rapidly. I'll aggressively research the product, the market, and the competition. I'll listen to our customers' biggest challenges, and show them how our product is a solution, if indeed it is.”
Finally, don't be afraid to tell them how what you bring to the table is unique. Say that no one else will listen better than you, work harder than you, or know their products and the advantages over competitors better than you. If you come in with this level of preparation, a concise explanation of what you provide, and the right attitude and energy, you'll have a much better chance at getting the head of a start‐up to roll the dice on you.
Notes
- 1 Patrick Henry, “Why Some Startups Succeed (and Why Most Fail),” Entrepreneur (February 18, 2017), https://www.entrepreneur.com/article/288769.
- 2 “Mark One,” Crunchbase, 2019, https://www.crunchbase.com/organization/mark-one#section-overview.
- 3 “Vessyl Digital Cup,” The Colbert Report (July 14, 2014), http://www.cc.com/video-clips/9nzwjt/the-colbert-report-vessyl-digital-cup.
- 4 Author interview with Kevin Klausmeyer, April 2019.