Brad Feld

Tag: mentor

Earlier this year Amy and I, along with a number of other local friends, supported the rollout of a new organization in Longmont called Entrepreneurship for All (EforAll).

EforAll is a nonprofit organization that partners with communities nationwide to help under-resourced individuals pursue their dream of starting a business. They believe everyone should have the opportunity, resources, and support they need to successfully start their business. Its programs include a free, full-year Business Accelerator that utilizes a cohort model and includes intensive business training and mentorship as well as quarterly community pitch contests.

Since I first wrote about their launch, EforAll Longmont has hosted two pitch contests featuring over 50 entrepreneurs. To get a feel for the activity, take a look at the article about Lorne Jenkins after he won the top prize at one of the pitch competitions.

EforAll Longmont is accepting applications for its first Accelerator program which will start in early January. To help these entrepreneurs, EforAll is looking for experienced professionals across a wide range of industries to serve as mentors for these entrepreneurs. I’ve written extensively about the importance of effective mentorship and one of the things that I love the most about EforAll is their mentorship model.

After spending time with a few EforAll entrepreneurs, I came away excited by their ideas and aspirations. What they need now are mentors who can serve as their champion, coach, and support network as they navigate the challenges of starting their own business.

If you are an entrepreneur or business leader living near Longmont, Colorado, especially in an adjacent town like Boulder, and you are interested in becoming a mentor for EforAll, please reach out to Harris Rollinger, the Executive Director of EforAll Longmont or volunteer online to become a mentor.


This is the final post (18) of the Techstars Mentor Manifesto. As with item 17, Jay Batson, a long-time Techstars Boston mentor, nudged me several times to finish this up and wrote a draft from his perspective. Following is item #18 of the Techstars Mentor Manifesto, in Jay’s words.

During one of the Techstars Boston cohorts where I’ve been Mentor-in-Residence, I worked with a 20-something CEO founder (code named Mary) who, shortly after raising a seed round of several million dollars, hired a high-powered exec, granting a significant equity option. This new hire was a commercial hustler (code named Scott), moving quickly and broadly to try to secure customers and partners, including some of the tech industry’s largest companies.

Mary had never managed somebody a decade senior to her and was struggling to manage Scott. Further, Scott tended to work autonomously, sometimes doing things outside his remit that was not well-communicated to Mary. As a result, Mary was worried about how this looked to her board. A massive sense of imposter syndrome started creeping in, especially since Mary felt investors had bet on her, yet Scott was having a notable impact, for better and worse, on the strategy and success of the business.

Mary was concerned that the investors thought she wasn’t being effective. A fear was brewing in the pit of her stomach and she worried that everything was going to come apart.

Pause for a moment. Recall the last time you had a consuming passion. Remember how it felt. Think about that incredibly exciting idea that grabbed you and took over your mind, time, priorities, and emotions. Remember how excited you were as you imagined all the threads of what could be, and how your heart beat faster and your adrenaline surged.

And then … you had an existential crisis. A moment when you feared that this awesome future might come crashing down because of a particular situation or the actions of one person. Your heart beat faster again, but this time out of worry, anxiety, and fear.

I want you to replay your joy and fears again for a moment. Having empathy requires you to feel what the other person is going through. To put yourselves in their shoes and feel their fear. And to not immediately try to fix it. Remembering your own hopes and fears will help you have empathy. And this is critical as a mentor because startups are extremely hard.

In the situation above, I could relate to Mary feeling imposter syndrome. My first venture-backed company was not a big exit, and neither I nor my investors fared well. So I felt some imposter syndrome when founding my second venture-backed company (which, happily, has done well.)

So what Mary needed from me as a mentor was to talk to a neutral third-party who understood how technology companies worked and who had felt the expectations placed on a founding CEO. She needed to talk openly about how she was feeling to someone not on her board or exec team, and to whom she could be fully and safely transparent.

Doing that first allowed us to get around to eventually discussing ways to handle the situation. I reminded Mary that first and foremost, Techstars mentors are here to coach her on how to manage athletes like Scott, so she should relax and look for help. She had time to handle the situation if Scott was indeed a problem, as his option grants had a one-year cliff and he was only a couple of months in. So, instead of feeling anxious and pressured into reacting, I encouraged Mary to focus on helping Scott be successful and assess things again in a quarter.

Several years later, after the company, led by Mary, was acquired and had a very successful outcome, she told me that the most memorable and important thing I did for her at that moment was to simply sit, listen, and relate to the feeling she was having. I hadn’t immediately replied with a solution to her problem. Instead, I started with empathy.

As a mentor, be aware when to suspend, or defer, your advice or judgment. The entrepreneur you are mentoring may not be in a head space to hear your solution. Mentoring is often an emotional rather than a functional or intellectual role. Take a breath and be empathetic, instead than jumping in to solve the problem. And never forget that startups are hard.

Jay Batson has been the founder of four companies, including two venture-backed startups, with some big success and disappointing failure. His biggest success is as founding CEO of Acquia, now an 800+ person company with offices around the globe. In 2012, Jay invented the “Mentor-in-Residence” role at Techstars. MIR’s spend near-full-time at Techstars during each cohort to help as extensively as possible with companies and help other Mentors be good at it. Jay has embraced this responsibility for every Boston cohort since then. He’s an LP in several Techstars funds and a direct investor in a selection of Techstars companies.


I wrote 16 posts detailing each item of the Techstars Mentor Manifesto. However, there were 18 items and, for some reason, I never got around to writing the final two.

Jay Batson, a long-time Techstars Boston mentor, nudged me several times to finish this up. I kept saying “I’ll get to it” but never did. So, he did it for me, with the added motivation of getting it up prior to the kickoff to this year’s Boston program. Following is item #17 of the Techstars Mentor Manifesto, in Jay’s words.

This item on the list might sound very similar to #4, “Be Direct. Tell the Truth, However Hard.” But, it’s different. This item (#17) has to do with you, not the companies.

You have been asked to be a mentor at Techstars because you’ve been successful as an entrepreneur and/or a leader. The managing director for your cohort trusts that you’ll help the founders. And those founders are betting – with stock in their company – that you’ll be good for them.

Because of your expertise, you are likely to quickly spot areas in their businesses that need work urgently.

Because you’ve read all the posts here about the Techstars Mentor Manifesto, you dutifully start by being socratic and digging into the fundamental thing that is broken. You are direct, telling the hard truth that you are deeply concerned about some area.

But at some point, you sense the entrepreneur isn’t simply following your lead. They aren’t changing some element of their business to align with your direction. So, you are more direct. You push harder and more forcefully because you think it’s important. But the entrepreneur continues to “not get it”.

And, just like that, you’re irritated. You shut down, you quickly end the meeting, or you push even harder. After the meeting, you vent to the Techstars managing director that this company is in real trouble because the founders aren’t paying attention to this element you find important.

We’ve now reached the point of this post: Never Be Destructive.

The moment you go beyond trying to get your point across to the entrepreneur and do something outside that moment that is less-than-supportive, you’ve stopped being a mentor. You are now simply a judge. Or, worse, a detriment to the company.

You have let your desire to succeed as a mentor become paramount. Your actions can easily shift from being helpful as a mentor to being hurtful to the entrepreneur.

If you let this state persist, your frustration will leak outside the safe space of Techstars. It might be something you say to an investor; which means you’ve now affected the company’s ability to raise capital. If you vent to another founder, you either hurt your own reputation or the mentee’s reputation. At worst, you may end up affecting their relationships with potential partners or future hiring candidates.

Being a Techstars mentor does not mean being 100% dedicated to being a successful mentor. It means being 100% dedicated to helping founders build great companies.

So, be robust if you have to in making sure they hear what you’re trying to make them aware of.

But when you leave the room, make sure you flip the switch and remain 100% dedicated to making them successful, whether or not you think they heard what you had to say.

Jay Batson has been the founder of four companies, including two venture-backed startups, with some big success and disappointing failure. His biggest success is as founding CEO of Acquia, now an 800+ person company with offices around the globe. In 2012, Jay invented the “Mentor-in-Residence” role at Techstars. MIR’s spend near-full-time at Techstars during each cohort to help as extensively as possible with companies and help other Mentors be good at it. Jay has embraced this responsibility for every Boston cohort since then. He’s an LP in several Techstars funds and a direct investor in a selection of Techstars companies.


I’ve been working on my next book, #GiveFirst, again. There’s a lot in it about the Techstars Mentor Manifesto and how to be an effective mentor.

Yesterday, I got a note from Jay Batson, longtime Techstars Boston mentor and now the Mentor-in-Residence for the program, asking if I had ever compiled the lists I posts I wrote about the Techstars Mentor Manifesto.

I hadn’t. He had conveniently done it in a Google doc so it was easy for me to list out the posts with links. They follow.

1/18: Be Socratic

2/18: Expect nothing in return

3/18: Be Authentic – Practice What You Preach

4/18: Be Direct. Tell the Truth, However Hard.

5/18: Listen, too

6/18: The Best Mentor Relationships Eventually Become Two Way

7/18: Be Responsive

8/18: Adopt At Least One Company Every Single Year. Experience Counts.

9/18: Clearly Separate Opinion From Fact

10/18: Hold Information In Confidence

11/18: Clearly Commit to Mentor, or Do Not. Either Is Fine

12/18: Know What You Don’t Know. Say “I Don’t Know” when you don’t know.

13/18: Guide, Don’t Control

14/18: Accept and Communicate With Other Mentors That Get Involved

15/18: Be Optimistic

16/18: Provide Specific Actionable Advice

17/18: Be Challenging/Robust but Never Destructive

18/18: Have Empathy. Remember That Startups Are Hard

Jay also reminded me that I hadn’t written posts on #17 and #18. They are now on my list to do. Thanks, Jay!

2/6/18: Jay wrote 17/18: Be Challenging/Robust but Never Destructive which is now posted.

2/7/18: Jay wrote 18/18: Have Empathy. Remember That Startups Are Hard which is now posted.


There’s a tenuous balance between telling someone what to do and giving advice. It’s especially difficult as a mentor, especially if you’ve previously been a CEO and are used to being “the decider.”

As a mentor, you aren’t the decider. The CEO you are mentoring is the decider.

This dynamic is also true for many board / CEO relationships, where the board wants the CEO to make the ultimate decision. As I’ve often said, my goal as a VC is only to make one decision about a company – whether or not I support the CEO. If I do, I work for the CEO. If I don’t, it’s my job to do something about the CEO.

While this is nice in theory, it’s difficult in practice. One of my strengths is that I tell a lot of stories. One of my weaknesses is that, according to my wife Amy, my stories go on 20% too long (she is correct.) Here’s an example.

I’m at a board meeting. The CEO, which I love working with, is trying to figure out what to do about a particularly thorny issue. I tell a story. He reacts with a little more data. I tell another story. Another board member asks a question. I tell another story. This one goes on a bit too long.

The CEO looks directly at me and says, very firmly, “Will you just tell me the fucking answer for once?”

I tell him the answer.

He was looking for specific, actionable advice. I was telling him stories. If he spent enough time processing the stories, he might be able to come up with the right answer. Or, since they are stories, he might draw the wrong inference and decide to do something different from where the stories were leading him. This CEO was aware of that and, in real time was having trouble processing the point of the stories in his context.

Fortunately, this CEO was self-aware enough to ask for specific, actionable advice in a moment where he needed it.


Two mentors in one of the Techstars programs were both people who I knew well. They hated each other as a result of being co-founders of companies that had been bitter rivals.

Each company was successful, but their paths ended up being very different. These two co-founders hadn’t interacted with each other, but the CEOs of each of their companies had some rough interactions. As a result, each of these co-founders thought the other was an evil person.

Each of the co-founders was technical, extremely smart, and capable. Not surprisingly, they gravitated toward mentoring the same companies.

After a few very awkward moments, I encouraged the two co-founders to let their pasts be history and to move on. I knew them each pretty well and expected they’d like each other and get along if they had an opportunity to reset things. Being mentors to the same company gave them this opportunity.

It turned out that they loved working together. At some point, the co-founders talked about their past. They had never actually met, and each realized that their emotions were a function of the hostile relationship between the CEOs. Since they were channeling these emotions, they realized this was a self-limiting perspective.

They became friends. In a few cases, they’ve been mentors for the same company. It’s been a great example of moving beyond whatever your past is and accepting each other as a mentor in a new shared context.


Last month I took two weeks completely off the grid. As part of it, I spent some time working on my next book, Give First. As part of that, I finished up the sections on Deconstructing the Techstars Mentor Manifesto. While I wrote a draft of this post over a month ago, It felt appropriate to publish this, and the next few Mentor Manifesto posts, after a wave of Techstars Demo Days that just happened.

#15 is “Be Optimistic.” It sounds simple, but it can be incredibly difficult.

As a mentor, your job is not to solve a founder’s problem. It’s to help. It’s to listen. It’s to provide feedback and data from your experience.

You can do this from many different perspectives. However, given the stress on a founder, it’s best to do this from an optimistic frame of reference.

Here’s an example of the challenge. You are a mentor to Maria, who is struggling with her co-founder Stephan, who has become unpredictable, inconsistent, and subdued. Maria feels alone, both on a day to day basis as well as in dealing with Stephan (there are only two founders in this case.)

As a mentor, you had a difficult co-founder experience in your last company. While the dynamics were different, it ended poorly with your co-founder leaving the company. While you haven’t spoken since you split up, your business was successful and acquired for a life-changing sum of money for each of you.

Your co-founder struggle is one that didn’t work out between you and your co-founder but was ultimately financially rewarding for each of you. You carry around this conflict in your head. On the one hand, you are pessimistic about where things between Maria and Stephan will end up. On the other, you know that even if their relationship fails, the company can still be a success.

You also learned a lot from your experience with your co-founder. Each of you made mistakes in approaching things during your conflict period. This hurt both of you and negatively impacted the company for a while. Your struggle with each other was public, and it ruined several other relationships with people who felt like they needed to choose sides.

Being optimistic in this context is difficult. But it can be done. Start from a positive frame of reference. Talk openly with Maria about the things that you and your co-founder did wrong as you tried to address your conflict. Be clear about how things could have turned out differently. Be introspective in your discussion and speak from experience, instead of giving advice. Remember to reinforce that even though your relationship with your co-founder ended up failing, your business was successful.

Let Maria have her experience as she tries to resolve things with Stephan. Try to be a positive influence in the mix to encourage her to do the work involved, even if they end up parting ways.


It’s been a while since I wrote a post deconstructing the Techstars Mentor Manifesto. The last one I wrote was number 12 of 18: Know What You Don’t Know. Say I Don’t Know When You Don’t Know. Since I’m now working on the first draft of my next book #GiveFirst (or maybe it’ll be called Give First, or GiveFirst – I haven’t decided yet) it’s time to get my shit together and write the last six posts.

Throughout Techstars, we tell the founders that “it’s your company.” The implication of this is that they make the decisions about what to do. Everything they hear from mentors is just data.

A lot of mentors are successful CEOs. As CEOs, they are used to being in control. However, in the context of being a mentor, they don’t control anything. The best they can do is be a guide.

Interestingly, the best investors understand this. One of the lines my partners at Foundry Group use regular is that we only want to make one decision about a company – whether or not we support the CEO. If we support the CEO, we work for her. If we don’t support the CEO, we need to do something about this, which doesn’t necessarily mean fire the CEO.

In the context of being a mentor, you still get to make one decision, but it’s a different one. You get to decide whether or not you want to keep being a mentor. Assuming you do, your job is to support the founders, no matter what.

Ponder the following situation. The company has three founders. While one of them is CEO, it’s not clear that the right founder is the CEO. In addition, two of the founders (the CEO/founder and one other founder) are struggling with the third founder.

It would be easy to size up the situation and tell the founders what to do. But that’s not your job as a mentor. Instead, your job is to guide them to an understanding of the situation. The best mentors will invest time in each founder, keeping an open mind about what the fundamental problems are. You’ll surface the issues, guiding the founders to understand that there are real issues, what they are, help them talk about them, and help them work through them to a resolution or a better situation.

You won’t try to solve the problems. That’s not your job as a mentor. But you will be a guide. At some point, it will be appropriate, as a guide, to say what you would do if you found yourself in a similar situation. But, as a great guide, you won’t force this outcome, nor will you be judgmental if the founders go down a different path.

Remember – you get to make one decision – whether or not you want to keep being a mentor.


Techstars Boulder Demo Day is this week. It always marks the true end of summer for me and it’s a reminder that I stalled out on my Techstars Mentor Manifesto series of blog posts.

The last one I wrote was #11: Clearly Commit To Mentor Or Do Not. Either Is Fine. It’s an important life rule – either commit or don’t commit – but choose! Mentor Manifesto #12 is also a good life rule: Know What You Don’t Know. Say I Don’t Know When You Don’t Know.

We all know Mr. Smartest Guy In The Room. I find him insufferable and have nicknamed him Mr. Smartypants. Unfortunately, there are a lot of Mr. Smartypants in my world as he inhabits the bodies of some entrepreneurs and the souls of a lot of investors. Regardless of who he manifests himself in, he’s still tiresome and when there are two of him in the room, watch out.

The best mentors are not Mr. Smartypants. While a great mentor knows a lot and has had plenty of experiences, she’s always learning. The best mentor/mentee relationships are peer relationships, where the mentor learns as much from the mentee as she teaches the mentee. There’s no room in this relationship for Mr. Smartypants.

I know a lot about some things. And I know very little, or nothing about a lot more things. My business and technology experience is deep in software, where even the hardware companies we are investors in (Fitbit, Sphero, Makerbot, Glowforge, littleBits, and some others) are what we like to refer to as “software wrapped in plastic.” At the essence of it all is software and that’s what I know best.

But I don’t know all software. And I especially don’t know vertical markets. We’ve consciously stayed horizontal in our investing, being much more interested in our themes which apply to many different vertical markets. But ask me about a vertical market, whether it be entertainment, real estate, insurance, auto, food, energy, or financial services and I’ll often approach it with a beginners mind.

In some cases I think something generic will apply to a vertical market. But when asked about something structural, even though I’ve had lots of different experiences, read a zillion magazine articles over the years, and might have some opinions, as a mentor I’m quick to say I Don’t Know, unless I’m confident that I do.

When I find myself in an “I Don’t Know” situation as a mentor, I immediately start trying to figure out who I can refer the entrepreneur to who might know something about the situation. And, just because I don’t know doesn’t mean I’m not curious about finding out more. I’ll often stay engaged and hear what the mentor has to say, just so I get the benefit of having more data in my head to play around with in the future.

I say “I don’t know” or some version of it at least daily. How often do you say it?