Tip #2: Find and engage great mentors.

Here’s the second of my series of posts on my top twelve startup tips from Techstars this summer. It’s about finding and engaging great mentors.

Most first-time entrepreneurs that I know only seek out mentors for their companies when they decide they want funding. They do it because they have to, as part of the process of attempting to raise money. To further the process, they begin to listen to and react to the thoughts of investors as a way of gaining favor. I think that this is very much the wrong way to think about mentorship.

Great mentors need to be weaved into the fabric of any startup from the beginning. Most people already have one or two mentors in their lives. Many don’t even know who their mentors are or have been until they reflect upon this for a moment. Often, I think that’s a good sign and indicates a positive mentoring relationship. For many, it’s their fathers, their best friends, a past boss, or perhaps a college professor. Stop for a moment and ponder the impact that these people have had on your life so far.

You need that same kind of impact on your business. It should be obvious.

How do you find potentially great mentors?

First, you make it a priority. Think about your own network. Who has vastly more life or startup experience than you do? Start there.

If you need to extend the net, the next step is to work your network. Start learning about local companies that you respect and consider seeking out their founders or key executives. A neat way of approaching them initially is to explain that you admire the business that they started, and would love to hear the story of how it was built in hopes of making your own startup successful. Do your research – know the basics of the story and prepare some questions in advance. Often founders of successful companies are actively engaged in the startup community anyway, and love thinking about other startups and meeting energetic founders that remind them of a younger version of themselves. Don’t just pick a mentor because of how they look on paper. Read their blog if they have one, and study the things they’ve done in their lives and in their careers. A great mentor for you is not necessarily a great mentor for everyone.

What makes a great mentor?

Ultimately, great mentors see something in you, and help you reach your potential. They don’t always do this with direct advice. Often, they do it with introductions, resources, or through the process of thinking out loud with you. Your best mentors will become friends and permanent fixtures in your life.

Approaching potential mentors

People make the natural but routinely incorrect assumption that great mentors would simply be too busy to help them. Ask anyone who has sought meetings with successful entrepreneurs in Colorado – I think you’ll find that when you approach people in our community you’ll find an amazing number of open doors. Most people just never knock on them out of fear of rejection. This is very silly. Imagine how good it must feel to be asked for advice from a smart, dedicated, and motivated founder like you. Keep in mind that you have something to give back too.

Engaging potential mentors

There is one final trick to getting the most from relationships with mentors. It’s not enough to find great mentors, ask a few questions, and move on. You have to engage them. By definition, they’re not a mentor until they’re actively engaged.

This sounds simple, but almost everyone screws it up. Engagement is not accomplishing by sending an occasional email updating the person on what you’re doing or the major news every once in a while. It’s not built by offering to take someone to lunch. It’s built over a long period of time with small, regular, interesting, and thought-provoking communication. In my opinion, the best way to do this early on is by email as it maximally respects the time of the mentor that you are engaging.

A great example

I want to give you a great example of how to do this. David and Heather Duey get this. They have emailed me dozens of times over the course of the last 9 months asking questions about their startup, Georneys. I’m connected to them only in a couple of ways. First, they’re from Tallahassee, Florida and I grew up in Florida and am a big Seminoles fan (yes, let the mockery begin). Heather and David knew that from reading my personal blog. Second, they’re doing a startup, and I love startups. That’s it – I had never even met them until after a remote mentoring relationship had developed. They first contacted me after applying for Techstars. When they didn’t get in this summer, they continued the dialog. They frequently emailed me with well thought out questions that allowed me to spend just a few minutes to get them some feedback on their business. Over time, they began to email me more complex or deep questions about their business. Now they’re coming to Defrag and planning to move to Boulder to be in a more entrepreneurial community. I know them personally now – and I like speaking to them about their business. They probably don’t know it, but there’s two way learning going on. For example, I’m a regular reader of both of their blogs and through them I’ve come to better understand some of the trials and tribulations of co-founding a company with a spouse (not that I plan to try that!).

Building the relationship

Once you have established a relationship, the key becomes regular engagement. While keeping the early relationship low-impact on the person you are getting guidance from is important, you can certainly step it up over time. The ideal scenario is to involve them directly in the strategy associated with the development of your business, your product, or you as a person. For example, you can engage the mentor by soliciting direct feedback on an early prototype of your product. Even if you get a trickle of feedback from them, you have the key ingredients of engagement. Think about their points, make at least one change or improvement that you agree with (there must be one!), and reply with an email succinctly detailing what you’ve done about each point. It’s OK (probably even good) to disagree with some of the points when appropriate – just efficiently explain why. In your response email, it’s key to ask them to give you more feedback now that you have made those changes. Keep the loop going in this way and you’ll develop a positive conversation with the mentor, improve the product, and build a relationship. This mentor will begin to associate you as with the concepts of strong follow up, willingness to be coached, logic and critical thinking, and most of all forward motion. What I’m describing is a process that allows you to build a remote mentoring relationship that is low impact for the mentor, but that ultimate leads you (if you’re good) to a point where asking for a meeting will likely result in success. From there, you can really get to know the person and continue this positive feedback loop.

Mentorship evolved

Brad Feld (who is certainly one of my mentors) wrote a terrific post about mentorship some time ago that has a special spot in the quick-access RAM of my brain. He said:

“…one thing stands out: the rare, but brilliant moment when the relationship shifts, the distinction between mentor and mentee dissolves, and you become “co-mentors”. Even if you aren’t “peers,” the learning becomes bi-directional. Everyone in a mentoring relationship should strive for this equilibrium, because it is here where the greatest learning occurs.”

I have some mentors that I’ve reached this stage with. David Brown was my co-founder at my first company, and was always someone that I consistently learned from. I think our relationship has reached equilibrium, and I hope that he learns as much from my knowledge and experience as I do from his. I haven’t worked with him on a daily basis in years now, but we still bounce important things off each other on a regular basis. We’re working in different worlds now, but are fascinated by what goes on in each.

The fruits of meaningful engagement with great mentors

At Techstars, when I look back at the companies who are seeing early success I see high levels of mentor engagement in all cases. They didn’t just take meetings with the mentors that we dropped in their laps. They engaged many of them that they respected in ongoing, meaningful, and independent conversation. They took advice for what it’s meant to be – something to think about. They reacted to the advice not just in the pursuit of pleasing the mentor, but in the pursuit of building value while being intellectually honest with themselves. They communicated regularly and effectively with their chosen mentors, involving them in the hard thinking that was necessary to build their companies. They regularly solicited feedback as they built their product, incorporating some of it and continuing the positive feedback loop with their mentors. They gave their mentors positive experiences with their passion, ability, product, and company on a very regular basis. The result was predictable. Those mentors were among the first to stick their hands up to participate in funding the company and continuing to stay active with it.


Great founders intuitively understand the importance and role of mentors. They seek them out for the right reasons and engage them on an ongoing basis. I think the presence of great mentors who are actively engaged (not just listing their names on the advisory board) around an early stage company is a strong indicator of future success.

file under: Blog, Startups