When I first heard the Jim Rohn quote, “You are the average of the five people you spend the most time with” it really made me stop and think. I had already hired highly competent people at work, but what was the state of my entourage outside of work?

Once I got serious about building Little Pim, I realized I needed to put myself into situations — work, social, and a bit of both — that would help me find people who would both cheer me on and challenge my thinking in new ways.

I needed to find peers and business people who were a few steps ahead of me and would help me grow in the areas where I needed help, such as managing and growing my staff, long-term strategic planning, fundraising and introductions to possible investors.

You probably already know that one of your most important jobs as CEO is to be a fountain of optimism and inspiration for your team. You must do what I call “hold the vision” for where your company is headed no matter how many twists and turns it takes to get there, so it’s critical to surround yourself with positive people who will help you stay in that mindset and help you grow. This might require taking an honest inventory of who you spend time with now.

Summit conversationsI noticed that when I did that inventory there were some people I just didn’t think helped me be that positive “vision holder.” I still spend time with my friends who like to point out all the things that could go wrong with my business, but got onto more of a twice-a-year-for-coffee schedule, and I steered away from talking about the company when with them. Then there were people in my life who were either too risk-averse themselves to be able to support me in taking the risks I needed to take to grow my business, or they just emphasized the risks in an unhelpful way.

One way to find new people who will support you and help you stay in that optimistic zone is to form an “Accountability” group or partnership with a person or people doing ambitious things. These groups are 2-5 people who meet regularly in person or via video conferencing, set monthly goals and make sure that they are each staying on track. These kinds of groups have proven invaluable in helping people get further, faster, and feel more supported while they tackle new challenges.

As you build your business and go outside of your comfort zone to learn new skills, you will need your “peeps” to have your back. What are some ways that different people in your life are helping – or hindering you on your entrepreneurial path? Who helps you stay positive and on track? Is it family? Friends? Is it checking in with peers or mentors?

Helping women get that support is one of the reasons I created the online group coaching program Million Dollar Women Masterclass. It offers a community of women going big as well as my teaching, access to successful female founders who have #BeenThereDoneThat and top mentors and coaches who can help get you to a million.  The next round of Masterclass starts May 17th and has limited space.

To book a FREE 45-minute Accelerate Session with me, and see if Masterclass is right for you, sign up here now before they’re gone. And take a moment to take a little social inventory right now, and restock on more positive, supportive and maybe just-slightly-ahead-of-you people in your life!

Stay brave,





3 thoughts on “Finding the Right Entrepreneurial Entourage

  1. Excellent advice, and so important.
    When I first started, I realized that I could NOT listen to many of my friends – who were not in my target market OR who have a much lower risk tolerance than I do.

    It’s great to find others who have done what you are doing and understand the highs and lows.

  2. Really appreciate your comment, Helena. You make an excellent point about the importance of understanding yourself (risk aversion, etc.) when it comes to hearing others’ advice. Thanks!

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