How to Manage World-Class Advisors, Investors, and Board Members

If you missed the event or just want a quick recap, read on for highlights from the discussion.

The event brought together world-class entrepreneurs and investors Jim Gray (CEO, G-Bar Limited Partnership; Co-Founder, OptionsXpress), Amanda Lannert (CEO, Jellyvision), Badal Shah (Co-Founder and CEO, TurboAppeal), Michael Small (CEO, gogo), and Kevin Willer (Partner, Chicago Ventures) to share their insights on attracting and managing advisors, investors and board members with panel moderator Pete Wilkins (Managing Director, Hyde Park Angels).

Key Takeaways

Whether you’re dealing with advisors, investors, or board members, a few principles remain the same. Honesty, understanding, and chemistry are vital to the success of the relationship, just like in all relationships. Moreover, the relationships don’t work unless you come into each one with clear goals for your business. The world’s best advisor can’t help you if you don’t know what you need help, and no amount of capital makes up for misalignment between an investor and you. Both themes came up again and again during the panel, starting with advisor relationships.


Finding advisors is not just about finding people with impressive backgrounds who you like. They have to add value to your business. Amanda Lannert made it simple by breaking out four categories of advisors: those who provide “strategic advice, access to capital, access to customers, and access to talent.” 

As an entrepreneur, you have to be laser-focused on seeking out the help you need, as opposed to listening to a jumble of different thoughts. Advice overload creates what Michael Small defined as “paralysis by advice,” and stressed that while “advisors are tremendously valuable, your decisions [are yours].” In other words, you should know what advice you need and find people who can truly give it to you, but still retain your own vision for the company.

While advisors are tremendously valuable, your decisions are still yours. Click To Tweet

Retaining your vision and making your own decisions doesn’t mean disregarding advice or tuning counterarguments out. That’s not productive for you or the advisor. As Jim Gray put it, “it’s not that they have to agree with everything I say, but I want to feel like I’m being heard. If they don’t want to be mentored, don’t get an advisor.”


One of the advantages of bringing on advisors early is that they may become investors, especially if you’ve maintain close relationships built in mutual understanding. However, there are risk to taking capital. In fact, nearly all of the panelists cautioned against taking on institutional capital unless absolutely necessary.

In particular, Kevin Willer highlighted, “If you don’t take capital, you hold onto your entire business. Bootstrap your companies if you can. Own them all.” Control and equity aren’t the only main factors you give up when you take capital. Amanda Lannert emphasized that “it’s very difficult to raise capital and get customers at the same time.” When you fundraise, you have to give up valuable time and energy you may need to grow your customer base, so you have to weigh the costs and benefits against one another.

However, if you need a first-mover advantage to succeed or an injection of capital just to keep up with sky-high demand, raising capital may be worth it. After all, said Badal Shah, “one percent of a couple hundred million is more than one hundred percent of zero.” Your investment decisions must hinge on what’s best for the company. If raising capital still makes sense for you, having advisors in place is a solid strategy for bringing on value-add investors who ultimately become value-add board members.

Board Members

Taking on investment means you need to prepare for a board of directors because as Pete Wilkins explained, “once you receive capital, most of your capital partners will want to be on your board.” Not all of your capital partners can or should be on your board; big boards lead to indecision and unwieldy meetings. Instead, you need to make sure that like your advisors, the investors you bring onto your board are value-add.

Nevertheless, just because they’ve invested capital and have deep expertise doesn’t mean you should simply cater to them. In fact, Amanda Lannert defined “one of the biggest mistakes entrepreneurs make [as] over-managing the board and placating the board.” While it’s important to remember that the board has a say in the direction of the company and ultimately determines who the CEO is, the company is still yours. You need to own your board meetings and manage your board effectively in order to ensure you’re acting in the best interests of the company.

One of the biggest mistakes entrepreneurs make is over-managing and placating the board. Click To Tweet

Amanda provided key steps for building good boards and managing meetings well. It breaks down into four key areas:

  • Keep your board small, three to five members is ideal
  • Leverage your advisors for help in managing your board members
  • Focus board member attention on strategy
  • In board meetings, own the agenda from start to finish

Michael Small and Pete Wilkins added to this list with their own key recommendations. Michael stressed that when “management and the board don’t understand their respective roles,” chaos ensues, so as the Founder and CEO, you need to reiterate your core responsibilities versus theirs. Pete Wilkins added that, “you can gain consensus [among your board members] by setting board expectations in board meetings.”

Photo by 1871/Gregory Rothstein