Background
When my startup was growing like crazy and I felt like we had product-market fit, for the first time in my career I tried to mentor some startup founders. In 2012 I reached out to a half-dozen founder/CEOs with a simple offer...

If you agree to meet with me for coffee every month and tell me everything, I'll advise you.

And I never asked any of these founders for any form of compensation.

My startup was well-known in town and I began to have a reputation as a helpful person to local founders, so I was able to begin to work with a few good founders.

Those relationships have since turned-out to be some of the best in my career, but I was struck in the beginning (and continue to be surprised today) at how difficult it is to mentor founders.

Why's It So Difficult?
Two years ago I wrote a blog post about this topic, but here's a few things that are non-obvious for people just starting to casually mentor founders...

1) Founders want to cut their own path. Think of the people you've known who didn't go to college so they could tour around the country until their rock band hit it big. Or the people living in east coast cities in the late eighteen hundreds who headed out west to stake their claim. Or friends who leave their steady jobs to launch a local restaurant. Startup founders are very similar in that the passion/vision/mission/itch of the goal is worth the (very bad) odds of success.

Because this is a group of people who (in the beginning) aren't being primarily guided by logic, mentoring can be tough.

2) The fog of war. A very accurate definition of a "startup" could be "an organization where you have to get outsized results from less-than-adequate resources." This means that every founder is constantly moving from thing to thing trying to make something out of nothing. So one day the goal is to hire a new developer, then next day the goal is to move into a new office space and the following day the goal is to get money from a new investor.

Because of moving priorities, mentoring can be tough.

3) That feeling that only founders know. While it might seem like the founder is super confident, things are going really well and the path is clear, each of these is only true about one day per month.

Founders (especially good ones) are great at making outsiders believe that everything is fantastic. The rest of the time the founder wakes up with a feeling that's difficult to understand unless you've been there.

Imagine a day where something bad happens to you. Maybe you crash your car on the way into work...and it's your fault. And on this particular day you have something important to present at work. Then imagine that on your Uber ride into work (after the crash) you get a call that your significant other just had to go to the emergency room.

This is close to the feeling that founders have. The feeling that things are bad. Then more bad stuff happens. And this will likely keep happening with no end in sight. And it's all your fault because you started all this. This is the feeling most founders have pretty much constantly until the business gets some traction.

Because of these constant, non-obvious from the outside, real or perceived existential threats, mentoring can be tough.

4) What you know might be wrong. There's another facet of mentoring that is tricky. Let's say you are the President of a 100-person real estate development firm. Or the VP of Marketing for a Fortune 500 company with an MBA. Much of what you've learned along your path is geared towards organizations at scale. Hiring best practices. Navigating successfully across departments. Strategic planning. These types of activities either aren't important at all for 3-person startups or the way they are handled are entirely different from big organizations.

Because many lessons learned are different based on the phase of the organization, mentoring can be tough.

So How Do You Navigate All This?
Just like successful rock bands, successful explorers and successful local restaurants, successful startups make our lives much better, so supporting their creators is important.

But what's the best way?

For anyone wanting to mentor startups I'd recommend doing five things...

1) Find the best founders. There's this term in the startup investing world called "deal flow." Ask a VC about what's most important to their business and the first thing they'll say is deal flow...how do they see the best founders and startups?

I'd encourage mentors to think in the same way. If you want to spend some time helping a founder, make sure this founder is coming from the best channels, so you know your time and effort are going to support the best founders possible.

So find people who are very connected to local startups and have them help you identify the best founders to support.

2) Put yourself into a bucket. I think about mentors in three buckets.

• Successful founder. These are people who have been on the journey before and created something meaningful. It doesn't matter if the company went public, raised millions of dollars or was bought for millions of dollars. What matters most is that this person burned the boats, convinced good people to work with them and built something that customers loved. The distance between this outcome and daydreaming about a startup idea is immense...if you've done those three things then you are a successful founder in my book.

• Investor. One commonality across 99.9% high-growth startups is that they need capital to grow. Because of this, investors into startups are very important to each founder's journey. Plus investors typically meet with lots of founders, so their instincts are good (even if they never started something themselves).

• Tactical support. The third important way you can help founders if you aren't a founder or an investor is to help them with tactical issues. If you are a lawyer, you can help with legal issues. If you are a finance person, you can help them with modeling. Or if you are an operations person, then you can help them there. The key point here is not to try and be an expert at everything the startup is facing. You might have friends who have raised capital for their startups, but be careful with giving capital raising advice if you haven't done it before. As much as possible, try to stay in your lane of expertise and make sure the founder is clear about it. I'd also encourage tactical mentors to learn how their area of expertise (eg financial modeling) is different between their current job and a 3-person startup. Learning the differences here is a great opportunity for you to learn because at one time your organization was 3 people and (trust me) the financial model wasn't as mature as it is today (and it didn't need to be)!

3) Identify your superpower. Whether you are a founder, investor or someone more tactical, I'd encourage all mentors to identify their three main "superpowers." These are things that you love doing and are naturally good at. Things that you'd do for free all day long if you could. Because these talents come so naturally to you, you'll enjoy every minute that you are teaching founders about these topics.

Identifying your superpowers also helps people in the startup ecosystem connect you to founders that need help in your areas of expertise.

Off the top of my head, my superpowers might be (a) how to get into a startup accelerator, (b) how to find good graphic designers and (c) consumer engagement. Even thought I'm a founder, these are topics that I have a deep understanding of and love talking about.

4) Don't ask or expect anything in return in the beginning. Maybe the single characteristic that attracts me to startups the most is the fact that all that matters is results. Say whatever you want about your big vision. Get the best advisors on the planet. Raise millions of dollars from top-tier VCs. None of this matters if customers aren't loving your product. Due to this clear & simple fact, anything that produces real results is super clear to everyone involved in a startup. And anyone providing true value will be rewarded eventually. So fight any instinct that you might have to expect compensation for your mentorship in the beginning. At Techstars we call this philosophy #givefirst and it's a fundamental part of the Techstars culture.

5) Be patient. Before you begin please know that this won't be one or two meetings and then your work will be done. I wouldn't start a founder mentoring relationship unless you are committed to many meetings over many months. And if the startup takes off, the relationship could even go for years. My most successful founder mentor relationship is now seven years old. And I just had breakfast with the founder a few days ago.

I tweeted more thoughts on this topic here.

One Last Thing
I hope none of this discourages anyone from helping startup founders. The relationships that I've built over the years as I've seen founders grow are almost as satisfying as seeing my own startup grow.

And this tweet describes the Techstars Mentor Manifesto pretty well if anyone wants to read more about it. Thanks @JeremyShure.

If this post resonates with you please forward it to one mentor (or should-be mentor) that you believe in. You'd be surprised at the ripple effects this will have.

Create great startups and help great founders!

#givefirst