Advice For Entrepreneurs Working At Big Companies

Tac Anderson
A Contrarian’s Guide
4 min readJul 18, 2015

In my first post I mentioned that despite my non-traditional career path, that I’m far from alone in my contrarian approach to blending entrepreneurial endeavors with corporate jobs. Over the last year as I’ve been reflecting back on this road less traveled, I’ve started reaching out to other entrepreneurs turned intrepreneurs, to pick their brain. I’ve decided to start capturing some of those conversations and sharing them with you.

This first one is an interview with Jason Falls (@jasonfalls). Jason is very well-known in the social media, blogging, marketing space (he’s kind of a big deal). He was an early adopter of blogging, regular public speaker, and author. Anyone who knows him, also knows he can be a loud mouth, overly opinionated, can come off a bit gruff, but he’s also one hell of a smart marketer. And for those who have got to know him, we know him as a loyal friend, he’s brutally honest because he cares, and he’s a devoted husband and father.

Jason has a non-traditional career path, holding a variety of jobs ranging from academia, owning his own businesses, working at publicly traded companies, and at marketing agencies. When I last spoke with Jason, I wanted to talk about those times he’s transitioned from entrepreneur to intrepreneur, what made them work, and what doesn’t.

Set Expectations Early

Jason commented early in our conversation that even though he’d known how bureaucratic working at large companies could be, he was still surprised that it was worse than he remembered. A common point of frustration for Jason was how companies allocate their budgets and approve funding new initiatives.

As an entrepreneur when you’re brought into a company it’s often to do something new, which requires new budgets. Once you’ve put together a plan and you’re ready to move, waiting weeks just to get the right meetings to get the approval you need can be infuriating. Especially when you end up needing more meetings and revised plans. When I asked Jason what he would recommend to other’s in this situation, he said setting expectations early was crucial, “You have to get in early and set ground rules for what kind of support you need, and make sure you understand how the process works internally.” He recommended getting a small budget approved that allows you some discretion to experiment, and then go for bigger budgets once you’ve proved your idea.

We talked about the challenges that companies have allocating budgets between set initiatives, and setting money aside for opportunistic investing. That money set aside can help fund exciting, new opportunities, but building a business case to get access to it can be painful. Too much structure creates bureaucracy, and too little structure creates churn. Jason said that he usually sees too little structure in startups that have grown really big, really fast.

I Imagine You’re Pretty Hard To Manage

Jason and I probably laughed the hardest when I brought up that entrepreneurs are notoriously difficult to manage. (Funny stories for another time.) Jason noted that entrepreneurs can benefit a lot from good managers. Managers that are leaders, who don’t micromanage but instead guide and mentor. Jason said that it’s important to establish expectations and ground rules. Weekly check-ins are important because entrepreneurs can get off track chasing shiny new objects very quickly. It’s a balance of providing enough structure, without stifling the entrepreneur.

Ideas Over Egos

Lastly we talked about trying to sell in your ideas. This was probably Jason’s most interesting comment. Entrepreneurs, turned intrepreneurs have to be able to give up some of their ego. They have to face the people pushing back on their ideas, put themselves in their shoes and understand what it is that they’re afraid of. They need to understand what’s going to motivate those people. What’s going to make them look good, what in your plan is going to drive their metrics, and what part of your idea can they own. You have to believe that the idea is more important than you getting all the credit. I personally think this is one of the hardest parts for entrepreneurs, besides maybe learning to deal with bureaucracy.

I had a great conversation with Jason, like I do every time we get a chance to talk. You should follow him on Twitter, and if you’re doing social media for your company, check out his book, No Bullshit Social Media: The All-Business, No-Hype Guide to Social Media Marketing.

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Tac Anderson
A Contrarian’s Guide

Entrepreneur turned serial intrapreneur / Contrarian / Phenomenologist / http://tacanderson.com/