Survival Guide for the Millennial Entrepreneur

Managing Partner, Made by Many

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 One of the most important things to understand about being an entrepreneur is that there is no such thing as a 9-to-5 or a five-day workweek. You are always thinking about your team, cash flow, customers, company, product, and about a million other details unique to your business. For each thing pulling on your thoughts and time, you are always on call and available to effectively suit up as a firefighter, referee, police officer, high-stakes negotiator, babysitter, garbage collector, disciplinarian, or peacemaker to deal with whatever your company, team, and customers are facing. Furthermore, for each suit you put on, you have to wear it until the job is done.

If you are an entrepreneur, you also don’t have a lot of capital, a well-established infrastructure, or a personnel hierarchy to turn to when things get tough. You are the end of the line. 

So what do you have? On the shortlist you have: yourself, your vision, your mental faculties, your network, and your sheer will to succeed. Regarding one’s will, if you’ve chosen the path of entrepreneurship, it means you are likely the professional equivalent of one of the soldiers from the movie 300. You have the ability to wear many hats, fight many battles, be available at a moment’s notice (and at any hour!), and withstand the financial and emotional ups and downs that come with starting your own company—no matter the industry. 

Implicit in these Spartan attributes are the concepts of flexibility and commitment. A word that embodies both is “resilience.” The etiology of resilience is particularly instructive here, as it is rooted in the Latin prefix re-, translated here to mean “back” and the Latin verb salire, or “to jump, leap.” The word resilience therefore connotes an ability to jump back in the face of mounting challenges, distractions, and obstacles. 

While resilience embodies flexibility (think of a bouncing spring), it also suggests that one must have endurance through not only the good times, but especially the pitfalls and failures. Just like Sheryl Sandberg suggests in her bestselling book, Lean In, one’s career is more of a jungle gym than a ladder. Similarly, one’s experience as an entrepreneur is more of a heart monitor than a hockey stick. In both the case of the ladder and the heart monitor analogies, there is a departure from some idealistic model of success that says: “Sorry, it is not linear, it is not contiguous, and it is not always headed in the ‘up’ direction.” 

As a serial entrepreneur who has been on the founding team of three companies by the age of 30 (Bradshaw Vineyards, JESS3, and Guide), I have had a number of jungle gym and heart monitor moments. When things got difficult, I mostly chose to weather the storm and have resilience. I also have found that there were times when the cost of enduring was not worth the expected outcome, which meant I decided to go in a different direction. 

At 31, I will be the first to admit that I am still a work in progress. However, when it comes to how I approach being a world class professional, there are five fundamental elements that have not wavered since as long as I can remember. These elements have helped me survive, thrive, and succeed in the face of just about anything. 

1. Master your craft. One of the most important things to do before starting your own company is to be the best at something. This is what you need to build your company around and why people will want to work with you, hire you, and invest in you. There is another important reason that you need to master your craft as a foundational step: you must have the ability to express high levels of discipline, commitment, and flexibility when you are running a company. When you are mastering a craft, you are showing commitment and discipline as well as remaining flexible as you learn new and more efficient ways to execute. 

When I use the word “craft,” you might think about design, textiles, or other forms of artistry. While I mean to encompass a much wider spectrum (operations, strategy, and team leadership are my crafts), I am purposely invoking the devotional aspects of these artisan pursuits. To be an artist is to commit to quality, try new expressions of your craft, and adhere to a regiment in order to master and perform your craft. What is your craft? How many hours do you spend on it each day? Do you have the right resources—teachers, tools, money—to become the best? These are important questions for which you need an answer. 

2. Develop a plan and adjust as needed, but make sure you’re following a north star. “If you don’t know where you are going, how will you know when you get there?” As simple as that saying is, it could not be truer. Whether you are putting together a roadmap for a month-long digital campaign, a mobile app, or a company, you need to clearly articulate the following:

            •          Your objectives – knowing what a win looks like is sine qua non

            •          Necessary resources – these include the nice-to-haves, must-haves, and a plan to fill any gaps

            •          Required steps – that also means having dependencies within these steps

            •          Concerns – name these at the onset so that you can work to solve them

            •          Constraints – time and budget are usually the main two 

Having a plan helps you be accountable to something sane in the face of chaos, while also helping your team understand both their individual roles as well as the big picture. If you are thinking about starting a company, developing a business plan is a must. I’ve read a lot about young entrepreneurs (and some investors) who don’t believe in having a business plan, because they focus solely on the quality of the product. It’s unacceptable though to not have to answer questions such as: How do you make money? When will you be profitable? What will it take to get you to profitability? Similarly, it is unacceptable to not know your strategy for engaging a target audience around a product launch. Both require varying levels of planning, but your efforts will ultimately not be successful without going through the exercise of planning and executing against the plan.

3. Find the right team members and partners. As someone who played team sports all through high school and participated in oodles of extracurricular activities like yearbook, Future Business Leaders of America, and student leadership, I’ve known this to be true since about age 10. Unfortunately, some people are still learning this lesson of teamwork the hard way and taking jobs simply because of the salary and the title. If you are doing this, stop. If people you love are doing this, tell them to stop. The number one qualification you should be evaluating when taking a job, building a company, or hiring a vendor should be this: Are the people A players who I can learn from and truly enjoy their company? If they are A players, but are rude, forget it. If they are fun to hang out with, but are C players who aren’t terribly motivated, don’t jump in. 

I’ve kept a list of the people I love working with that embody both of these attributes—excellence and a positive demeanor—and look to partner with them or flat-out hire them whenever I can. For instance, my officemate at my first job in Washington, D.C., became one of our lead strategy managers at JESS3. Not only was he super sharp and great at any task you threw at him, but he was also a true pleasure to work with daily. We laughed often, divided and conquered assignments, and delivered hard on our projects. We also earned battle scars together while in the trenches (at both jobs) and have implicit trust in one another. He is just one of the dozens of examples of team members I go out of my way to hire (even when they are in another time zone or country). 

Who are the people you’ve enjoyed working with due to their talent and their energy? Do you stay in touch? They should be the first people you call when you are in a position to hire people, especially if it is at your own company. 

I also want to underscore for the Millennials reading this: you need to partner with people that are older and more experienced than you are. That doesn’t mean you still can’t be your company’s CEO, but it does mean that you need to establish an advisory board or even formal board of directors to help guide you. You should also be prepared to hand over the reins if the time comes to scale your company beyond your wildest dreams; Ev Williams did it at Twitter and Andrew Mason just did it at Groupon. 

4. Treat everyone you encounter along the way with civility, dignity, and respect. These are things we learn at a very young age, and yet I have been shocked at how many adults don’t practice them. There is absolutely no excuse for being a jerk, for yelling, for making personal attacks, or for talking down to someone. I’ve been on teams where the supposed leaders acted in these ways and they didn’t just lose trust and respect. They lost highly talented people, contracts, and money.

Conversely, I have also worked with people who do an amazing job of keeping their cool despite difficult situations, who are great at listening to feedback from every level of the organization (and actually implementing it), and treat people who are performing even the most basic of jobs as equals. 

5. Be ready to be uncomfortable and spread thin, but not all the time. When you are building and mastering anything, there is going to be a certain amount of uncomfortability and multitasking that you are going to have to do. Especially in today’s always-on, always-connected, incredibly global marketplace, you are going to have to get on a lot of planes, take a lot of off-hours calls, and respond to requests on the weekends more often than not. When you are building an enterprise, you are going to have to wear a lot of hats while you get set up. I was part head of strategy, part head of client services, part head of PR, part head of admin/finances, part chief of staff, and part head of HR for my last company—and it took nearly four years before we had the capital to hire people that allowed me to relinquish some of those roles. 

The “but not all the time” bit is perhaps one of the biggest things I’ve had to learn in the last five years, as I thought I was supposed to be a Spartan warrior all of the time, in constant battle, with little sleep, and lots of hardship. As I write this essay from my apartment in Miami, which has a 200-degree view of Biscayne Bay, and get in an elevator to go down 24 floors to work alongside one of the smartest, kindest, and most hard working boss-partners I’ve ever had, I can’t help but saying out loud: I was making it too hard before. I wasn’t sleeping enough. I wasn’t eating right. I wasn’t exercising. I’ve also worked with people who don’t follow the tenants that I laid out in #4 above. Not anymore. 

If I could sum up my experience so far in just one sentence, it would be this: it is not going to be easy, but it will be worth it.


Leslie Bradshaw is a fellow at the U.S. Chamber of Commerce Foundation and the chief operating officer at Guide, a software company focused on turning online news and blogs into video. Prior to launching this new venture, Bradshaw co-founded and served as president and chief operating officer of JESS3, a creative interactive agency specializing in data visualization and visual storytelling. Bradshaw, a Phi Beta Kappa graduate of the University of Chicago, also is a regular contributor at Forbes on the topic of female entrepreneurship.