A Survival Guide for the Millennial Entrepreneur

I’ve co-founded three companies and am helping to scale a fourth. Here’s what I wish I knew at the beginning of it all.

Being a young entrepreneur is like being a Spartan soldier in the legendary army of 300. You’re taking on established, well-resourced incumbents and need to be well-armed and extremely resilient to not just survive, but win. Image courtesy of Pop Sugar.

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 Spartan 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. To paraphrase Pattie Sellers, Senior Editor at Large at Fortune and Executive Director of Live Content at Time Inc., ‘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 the coveted 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 instead 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 the now defunct text-to-video startup Guide) and (currently) the managing partner of a company expanding to the U.S. from London (Made by Many), I have had a number of jungle gym and heart monitor moments in my career, while helping build four companies. When things get difficult, I mostly choose 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 32, I will be the first to admit that I am still a work in progress. However, when it comes to striving to be a world class professional every day, in every interaction, and through every project, there are seven (7) fundamental elements that have not wavered since as long as I can remember (arguably, back to grade school days). These elements have helped me survive, thrive, and succeed in the face of just about anything. I hope they can be helpful to you on your journey.

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 equal parts commitment and discipline, while at the same time remaining flexible as you learn new and more efficient ways to execute and as you learn and apply advancements in your field.

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, the build plan for a mobile app, or the business plan and foundation for your 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. My counter-argument? It’s unacceptable 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.

The folks over at LivePlan have an excellent SaaS product that will allow you to drag and drop the necessary sections — and will autosave for you so nothing is lost and other team members can collaborate in the document.

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 talent and / or motivated, don’t jump in.

I’ve kept a list of the people I love working with that embody both of these attributes — professional excellence, craft mastery, 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, DC, 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 work ethic, talent, and their attitude? 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 who 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; Amanda Steinberg did it at Daily Worth; and Andrew Mason 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 fail to practice a rule that has been deemed ‘golden’ it’s that important. 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.

So which are you? Which do you want to be? Who would you rather work with or work for?

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 JESS3 — and it took nearly four years before we increased our margins so that we had the capital (and, frankly, time and brain space) to recruit, train, and 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 over the course of my career, 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. Not so. 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 tenets that I laid out in #4 above. Not anymore. (NB: I will be detailing this transition further here on Medium as a part of The Li.st’s collection on December 2, 2014!)

My realization? In my twenties I was thrashing around in the water, trying to keep my head above it. In my thirties, I realized it was only three feet deep and I stood up.

6) Take notes at all times and make every meeting actionable. This is perhaps one of the biggest things in which I have seen my millennial cohort (and those a bit younger than me) fail. Chalk it up to over-confidence in being able to recall things days (weeks even) after the meeting happened, or to a lack of experience to know how valuable people’s time is… but don’t let these things be your excuse. When you meet with one or more people, you are starting to accrue real costs for which you should be able to point to tangible, objective-achieving outcomes. Whether you measure costs in “billable hourly rates” or in “opportunity cost” (or both), you are eating into company resources and busy people’s time. So you better make it worth it.

Write things down in the moment so the information has high fidelity; return to them and organize them; take and assign action from them; and follow through until what was needed is achieved. Moleskins, Google Docs, and task management systems like Asana (and, admittedly, Post-It notes and Google Calendar for lighter tasks) are my “killer apps”.

7) Learn the art of explanation and persuasion in written, visual, and verbal mediums (or “media” for the Latin-conscious). And know when to use either (or both). Explaining things concisely and clearly should be one of your top goals as an entrepreneur. So should presenting a compelling argument that persuades your audience to believe your viewpoint or take the action you are recommending.

Study and master oration techniques from civilization’s best (personal favorites: Cicero and Mark Twain). Study and master how to formulate an argument. Know how to declare a thesis (or present a hypothesis) and defend it with fact-based evidence (obtain Strunk & White’s Elements of Style and read and appreciate George Orwell’s “Politics and the English Language”). Know how to visually story-tell with data, with integrity (see especially: The Wall Street Journal Guide to Information Graphics: The Dos and Don’ts of Presenting Data, Facts, and Figures). And if you really want to be well equipped: brush up your scientific method skills so that you can run your own experiments to test hypotheses and generate evidence (and to better understand data from other sources). Turns out Eric Ries’ Lean Startup is a great modern, startup-centric application of the scientific method we all used back in the three-panel science fair days in grade school.

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.

Originally published in the June 2013 edition of the Business Horizon Quarterly by the U.S. Chamber of Commerce Foundation, where I serve as a fellow. NB: I’ve since updated it to reflect both additional and revised thinking from the last 17 months.

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