In Episode 17, I chat with Alison about her business and leadership learnings from her deep experience founding, advising, and investing in businesses. We discuss topics like presenting and selling yourself, making tough decisions, and productive patience.


Alison is a strategic management consultant, serial entrepreneur, investor, and lecturer with expertise in building businesses. She has written various papers focused on entrepreneurship and growth strategies, she sits on the board of private equity funds and some early stage ventures, and frequently guest lectures at top universities. She has a podcast called “The Unapologetic Capitalist” and is currently finishing her first book by the same name, which will highlight the thrill of the entrepreneurial ride and offers frameworks to build long-term value for your venture.

How she became The Unapologetic Capitalist

  • During lectures she would introduce herself as an “unapologetic capitalist” and found some students had a negative reaction – the word “capitalism” has become cringe-worthy
  • Explained that her perspective is about building long-term sustainable value
  • Didn’t know her career would take her here, but always intended to have options that would allow her to create long-term value

Always know your exit goal. If you don’t know what that is, how do you even know you’re going in the right direction?”

  • Started as a strategic management consultant. Started a few ventures after business school
  • Still does a lot – very entrepreneurial, advises companies, invest, lecture. Gives her relevant, recent perspective.

Presenting and selling yourself

  • Most people don’t like talking about this – it doesn’t feel great to put yourself out there, to feel vulnerable
  • It’s a misnomer that vulnerable = weakness.

I really believe that vulnerability actually shows a significant amount of strength.

  • 20 years ago it was considered tacky to “toot your own horn” – meant your work didn’t speak for itself. Today it’s a point of basic validity to have yourself out there.
  • Unapologetic Capitalist episode on this is about how to tell your own story.

The most important thing is that you’re very comfortable with the simple truth of your own story.

  • Must also come to acceptance as to why you need to do this – the way you’re presenting and selling yourself is the optimal way for you to create value in your job, in your brand, for your product, etc.
  • Also think about the “who” – the audience to whom you’re telling your story. Attributes you emphasize will vary by audience.

Buy into the WHY you need to do it and understand the perspective of WHO you’re selling to.

  • Younger people tend to be insecure about the lack of years of experience, tendency to overcompensate in trying to appear confident. Need to be ok with where you are in the career and show you are open to perspectives to those around you. Communicate your story in a relatable way.
  • Listen to her show on Selling and Presenting Yourself.

The smartest people I know say things in the simplest terms.

Leaders vs Managers

  • Two distinct functions, must work well together.
  • A leader drives the vision of the venture. A manager helps implement the steps along the way to support that vision.

Women don’t have more challenges in being a leader… but in today’s society women have less latitude to fail than men do.

  • People can be both leaders and managers and be more strategic or more tactical as needed.
  • Some managers try to become leaders and fail. Not everyone can be a leader, it’s very difficult.
  • Listen to her show on The Different Roles of Leaders and Managers

I think leadership can be inspired. I don’t think it can be taught per se… but I also believe it can come from almost anywhere.

What to do when it all falls apart

  • Negative topics like dealing with conflict, things falling apart, fear of failure etc. are very real things but hard to talk about with peers, because you don’t want to seem vulnerable, or face negative consequences of sharing those fears.
  • Podcasts dealing with this topic are the most popular
  • Problems also revolve around relationship going bad – someone needing to be terminated, deal falling through, etc.
  • These are almost more common than the successes, but people don’t talk about them. People want to hear about success.
  • “Take time to grieve” – Need to take some time to vent before you can pick yourself up.

Need to have a healthy way to grieve about [failures] without guilt, without thinking you have to think positively all the time. You don’t!

  • For clients she advises, often her key job is to provide an outlet when they are exacerbated. Deliverables might look like a business plan or a deal, but the “penalty-free venting” is invaluable.
  • Exceptional leaders can be frank with their teams about how things might not go as planned, but communicate that the team can rely on them.
  • In the end, it’s not that everything always works out, which makes you a good leader. It’s that you were consistently reliable, in good times and bad.
  • Listen to her show on What to Do When it All Falls Apart.

Making tough decisions

  • Most decisions are difficult.
  • Tough decisions often involve ending relationships (employee, partner) or even winding down a company
  • You’re having to admit to a profound failure. Failure feels awful.

Try to check your fear and ego at the door.

  • Must prioritize the long-term value you’re trying to create over individual needs (wanting to be liked, feel good, etc.)
  • Good leaders take responsibility while bad leaders place blame or make excuses.
  • Listen to her show on Making Tough Decisions

Your good intentions do not alleviate you from the responsibility of the outcome of your decisions.

Productive Patience

  • Sometimes patience is productive.
  • Early stage companies have a very hard time with this. Lots of pressure to make things happen immediately.
  • Also see this a lot with mergers and acquisitions – sometimes you have to be willing to let certain options play out.
  • Sometimes you just need to hold on tight and “whiteknuckle it” to get through the rough patch and to allow things to play out.
  • Not asking you to neglect your garden – that’s complacency.
  • Listen her show on Driving Results with Productive Patience