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Question: Knowing what you know now, what career short cut could you have taken to get to where you are more quickly?

Trust Your Journey

“When I look back at my career, the journey makes sense in hindsight. Each experience, even those that were tangents, led to building the business. There might be shortcuts but appreciate the wisdom gained along long journeys. If you surround yourself with the right people, you don’t need to have a specific resume of experience, hefty capital or even steely confidence to start a business.”

Raise More Money

“Raise more money even if it means taking a smaller piece of a bigger pie. Doing so will allow you to focus on strategy and develop yourself as an executive instead of bootstrapping and getting stuck overseeing menial, repetitive tasks.”

Chase One Dream at a Time

“Because we are distracted by a massive influx of information from our peers, Millennials are always chasing multiple dreams at once, which rarely accomplishes anything at all. Have foresight and break those dreams up into three- to five- year periods.”

Trust Your Drive

“I was someone who was always looking for extra advice whenever I came across something I didn’t understand. That’s a good strategy, but what served me better and faster was trusting in myself to research everything and make the right calls on my own. There are a lot of levels I would have moved up faster if I trusted myself enough to start moving without waiting to hear from someone else.”

Spend More Time Networking

“It really is about who you know that gets you the best career shortcuts. Rather than spending extra time hunting for jobs, you could use that time to network and find more connectors that could help move you up the career ladder faster, introduce you to a new career that pays better and challenges you more, or helps you get the funding you needed to launch your business much sooner.”


“The path I took made me who I am and gave me the knowledge necessary to be a successful entrepreneur. It’s not always about what’s quicker or easier.”


“For a long time, I focused on just one thing: writing books. I’d published four of them in a short period of time before I realized that I was cannibalizing my own sales, that nonfiction wasn’t especially lucrative, and that I only needed one book to establish credibility in my industry. I wish I’d been content with the one successful book and branched out into speaking and consulting earlier.”

Delegate Much Earlier

“As founders, we start out doing everything, but as the company grows we forget that this is no longer necessary or sustainable. Looking back, I would have performed an 80/20 analysis on my daily tasks list and delegated my most time-consuming tasks (that didn’t generate revenue) much sooner. Not taking the time to take a hard look at the average day slows growth tremendously.”

Spend Less Time in College

“While I am still happy I got a master’s degree, I could have gotten onto the career ladder a lot quicker if I had postponed pursuing a second degree within a physical college environment. Instead, I could have received my degree virtually while starting my career earlier. College is a great experience, but being out there on the front lines and helping to build a company is even greater.”

Start Earlier

“Honestly, I don’t know if there is a career shortcut to being an entrepreneur. I started really young, but the only shortcut would have been to start my own company sooner — with less experience — and learn from there.”

Take On More Internships

“I had three internship experiences in college, but I now realize that you can never have too many. The entertainment and media industries are all about connections, and very rarely about your GPA. Networking and gaining contacts while you’re still in school is imperative to entering the business world. People often don’t care what you know, because that’s easy to teach; they care more about who you know.”