The Tao of Brad

Last week I was on a long mountain bike ride and wound up spending a few hours grinding away on a particular difficult situation one of the CEOs I work with was going through, when some advice Brad Feld gave me years ago popped into my head and I knew it was just what my friend needed to hear. I pulled off the trail, sat down in the dirt and called the CEO. As you’d expect, the idea was well received and I got a call the next day saying he’d already implemented it and how helpful it was.

It struck me how many often I’ve used something I’ve learned from Brad and I began to imagine how many times others have done the same; call it the Brad multiplier effect. I decided to reach out to folks I know who have benefited from a relationship with Brad and see what the most valuable insights they’ve gained from knowing him. What you’ll see here are the responses from a broad spectrum of entrepreneurs, CEOs, angel investors, venture capitalists and friends who’ve spent time with him. I can’t imagine how many more people have similar anecdotes and hope anyone who does will share them in the comments below. 

I’ll start with my own. Years ago, I was wrestling with a significant life decision that while incredibly important to me, didn’t have a sense of urgency attached to it. I reached out to Brad and the next time I saw him we went for a walk (another jewel I’ve learned from him; deep conversations seem to always have more value when away from desks, conference rooms, and other distractions). He listened carefully and when I was finished, he took a deep breath and said “You can’t process when you’re processing.” What he was telling me was that you can’t force a big decision and that the more you let go of it, the clearer it will become to you over time. Of course he was spot on and sure enough, when I stopped squeezing the decision, I ultimately arrived at (in hindsight) one of the best decisions I’ve made in my life. I’ve shared this wisdom with so many others over the years and it’s had as big an impact on them as it did for me.

Below, you’ll find all of the responses I received. Instead of giving attribution, I thought it would be more impactful if they were anonymous. Knowing Brad, he’ll have fun trying to connect the dots.


As an investor, I’ve learned from Brad that just as you can’t time the public markets, you can’t time the private markets either. I learned from him to invest the same amount of capital year in, year out, in roughly the same number of investments. Ignore the macros. Sometimes you’ll pay too much, sometimes you’ll get a deal and sometimes your investments will be priced fairly. If you do this over a couple of decades, it will all smooth out.

Don’t optimize on price. It never, ever pays off if you’re playing the long game.

Do or do not. There is no try.

I was talking with Brad about angel investing and he shared with me the importance of a portfolio approach and how anyone angel investing should plan for a minimum of 10 investments. “Take the money you have allocated to this asset class and divide by a number 10 or larger.  If you are not going to make at least 10 investments you should make zero.” I took it to heart, made 28 angel investments and have given that same advice dozens of times.

The long game is the only game worth playing

“Give First” — obvious? Yes, but you asked.  This is not something that he has ever said directly to me, but rather it has been my personal true north as it relates to giving first being one of life’s greatest journeys. Brad’s generosity of giving first is fundamental to his personal and professional ethos.  He gives first of himself as a friend, as a mentor, and with his wisdom. He gives first one the most special level philanthropically, not just in dollars, but with time and most tremendous impact.   Brad also gives first by “going first”— in one example, his openness of his own challenges makes him such a special friend in his empathy and understanding. Giving first has become a personal mantra — and it’s through Brad that I’ve fully understood that it’s not a business lesson nor a personal lesson, but a way of being that has created such a fulfilling life. This lesson has had the greatest impact on me in literally every aspect of my life.

Don’t ask me what I’d do. Do what you’d do.

To respond to everyone, no matter who it is or how big or small the ask is because you never know when you may encounter that person again. After 15+ years of working for Brad’s companies, I still don’t know how he does it!

The best advice and insights I’ve received from him came through his use of the Socratic method in our discussions. Two questions he asked me a long time ago still inform my journey in life: “Is this what you want to be doing 5 to 10 years from now?” and “Are you having fun?”

The best advice I have gotten is from simply watching him and I’m lucky to have had so much time with him.

While not advice, I think of the “Dairy Queen Lesson” a lot — one of my favorite things about Brad is how much emphasis he puts on meaningful time and deep dedication to his loved ones.  Meaningful doesn’t equate to big events, hallmark holidays, or occasions, but rather simply investing time with those who are the most important to us, even on the most simple level of sharing an ice cream.  The way he talks about his partnership with Amy and the tremendous respect and love he has for her.  This has helped shaped my own view of marriage and communication with my wife.  I call it the Dairy Queen lesson because of the photos of Brad and his dad through the years, each and always with tremendous smiles and ice cream 1, ice cream 2, and on even ice cream 3 in a day. Those smiles and that mutual love and admiration know no bounds.  This lesson has had a powerful impact on me and have informed my own approach to life as a husband, a father, and a son, a brother, and of course, a friend.

Be intellectually honest with yourself.

So much. However the one that sticks out is right before I became CEO of (xxxxx). I was struggling with maybe it was time to move out of Boulder. I just had my second failure as a CEO and I felt like I needed radical change – and he said “You can move, but that isn’t going to fix your issues – they are inside of you and they will travel with you wherever you go. Stay where you are, get super involved with Techstars and become the most engaged mentor ever and maybe something good will happen when you give more.” Of course I don’t recall his exact words and this is more like my recollection of an entire conversation is summed up in that one quote – but the essence is the same. So far it’s turned out pretty good 🙂

Strangely the best piece of advice I ever got from Brad didn’t actually come from him telling me something.  It came from watching him.  Brad’s willingness to help people without ever expecting anything in return really impacted the way that I think about giving my time to people I don’t know.

I owe my morning routine to advice I got from Brad and it’s had a major impact on me. I’ve found having a routine for getting yourself out of bed is a key part of being able to wake up early. Other wisdom he’s shared with me that I value include establishing a cadence to your life (weekly, quarterly, yearly) and his matrix on cultural fit.

Spend your time with A players if you want to become an A player. Watch them, study them, learn from them.

Doing something for myself on a regular basis. Not my company. Not my wife. Not my kids. Do something that nourishes me or I’ll be useless to everyone else. Took that to heart. Changed my life.  

That’s a hard one Mark – so much good advice from Brad over the years. The best may be something he actually said to someone else, which was the way to best help your community is to do what you’re awesome at (he was responding to someone asking him: “what can I do for you?”).

The good thing about venture capital is you can only lose 1x your money!

So much of the advice that I get from Brad is situation specific. I can’t say that I actually recall him ever giving broad advice vs highly specific advice. One generalization that I will make that I’ve noticed him do often though – when someone will come to him and ask about a tough decision where they are torn between various paths for all these intricate and complex reasons, he’ll cut through the fog and ask some incredibly simple question like “what do you actually want to do?” and then the rest of the discussion is about what if you just did that. He naturally challenges the assumption that these sorts of decisions have to feel heavy, and that’s been a valuable perspective for me to absorb.

To believe in myself.

Hmmmm. I think it’s the concept of taking care of yourself and being healthy; being true to yourself, as well. He’s always been a great supporter of doing what’s best for me even when it’s wicked hard.

Back when I was leaving (xxxxx), I barely knew him, but he took the time to go back and forth with me over email to help me think through some of the things in front of me and I think that email exchange was a big reason I didn’t go do another big corporate exec job. He talked with me about an offer I had at (xxxxx) to move to (xxxxx) and run (xxxxx) and their (xxxxx) business and how I’d spend my time dealing with their legacy tech and fixing old shit that other people broke and how depressing that probably would be, which really resonated with me.  It was the last time I ever considered any sort of bigco exec role.  We talked about viewing opportunities on a disruptive scale. I ended up choosing the “middle path” with that decision and joined (xxxxx), eschewing xxxxx which was on the more disruptive path. Of course, I ultimately joined (xxxxx) to be on the much more disruptive path 🙂

Guilt is a worthless feeling.

The importance of unplugging and being present.  In a fast-paced and sometimes frenetic world, the lesson of unplugging for a digital Sabbath, for time off the grid, and for time with family has been advice Brad has imparted on me.  In one instance, I shared with Brad that I was using social media more than I had wanted to, that I didn’t feel good about it, and I then riffed on a million excuses of why I still did it when I didn’t feel good about being “always on.”  Brad simply said, “why don’t you just stop? Take a break from it for a few months — honestly, what’s going to happen?”  Simple, to the point, and spot on.  The bigger lesson here was being present for our loved ones and for ourselves.  To enjoy life’s special moments. He was right. Stepping away helped me gain an entirely new perspective about letting technology be a tool and not a master.

Don’t get in over your head.  Figure out what you don’t know, and find someone that knows. Don’t fuck it up. Do the thing you love. The simple ones are my favorite.

Nobody stays here by faking reality in any manner whatsoever.

Gosh.  I feel like in so many ways he is another father figure for me. Our interactions over the years have been laden with advice and perspective that I have completely woven into my life. The introduction of the Socratic method into my life is probably the most significant impact he has had. It has changed how I process the world and how I interact with others. He has really shown me how my black/white tendencies can get in the way. Living with buffer around the edges makes things so much better. If you think you can sell something at $10 per unit, yet someone is offering 9.5, stop and think about whether or not a bunch more effort is worth the 0.5; 99% of the time it isn’t, and it’s ego that’s driving you to do silly things just to get exactly what you want. I find his advice is hidden… it rarely comes out as “advice.”

Give first with no expectation for anything in return. Good things always happen.

I have to pick just one? Brad and I went for a walk years ago. I asked him for advice/feedback on trusting myself as an investor. The gist of the advice was “figure out if you even like being an investor before you worry about your performance as one.”

“You would really enjoy mentoring at Techstars.” Brad gave me this advice during the first time we spent time together, on a walk with smoothies through Boulder Creek Park, many years ago.  This suggestion has changed my life in some of the most powerful ways possible. Many programs of mentorship later, I’m so lucky to be part of the Techstars family; from the people, to the companies, to the incredible friendships across the board. For that suggestion, I will be forever grateful to Brad, who plugged me into the Techstars ecosystem.

He told me I was lonely and didn’t seem to realize it. First time it occurred to me that you could be married and lonely.

I actually don’t think it’s anything specific he says but rather how he thinks about the world. He can look at situations intellectually, acknowledging the emotional charge, but not impacted by it. And he can tackle difficult subjects in non-confrontational ways. That’s pure art. He can, more rapidly than anyone I ever met, identify a situation’s biggest asset and also biggest liability, and reorient a path forward around its asset and minimize the liability.  I’ve seen him do this so many times in so many different situations in under 10 minutes. It’s mind blowing. He comes from a place of love and acceptance and generosity. Which is huge given the demands on his time and resources.  He’s probably the least religious person I know who most successfully embodies the teachings of most religions. He’s a philosopher stuck in a VC’s body. He is always asking why, about everything, helping to easily identify what’s important and what’s not. He’s curious about the world, and the space he puts between stimulus and reaction is what enables this curiosity and philosophy. It’s powerful and something I try hard (and often fail at) emulating. He inherently trusts people, which cause them to trust him, which leads to the attainment of their individual highest potential self.  Brad trusts the PERSON, not the outcome. So because he gives them that power of “I’ve got your back” they try risky things, and when combined with his ability to identify the assets and minimize liabilities rapidly, he and a founder is often a winning team. He lives his values. Most people I know speak their value, but act so differently. The hypocrisy has made me so negative on so many levels. But Brad is a breath of fresh air there and gives me faith that people in positions of influence, leadership, and wealth can and do act in the best interests of others. To sum it up, from my perspective, he has transcended the elusive barrier between knowledge and wisdom. I know a lot of smart people. Brad might be the only wise one I know. Wise, but still human. This email was fun to write and think about. If he ever decided to run for office or start a religion, or even start a country, I’d drop everything and support him. And I’m not the groupie type.








What To Look For

One of the questions I’m frequently asked by entrepreneurs is “what is the most important skill set to look for in recruiting and adding board members for my company?” I’ve watched this debated by my colleagues as well – operational, sales or finance expertise, product knowledge, a vast network and CEO coaching skills are among a host of attributes consistently discussed.

All of these are important characteristics to look for when adding people to your board and you should recruit based upon gaps in skill sets in the makeup of the board. I believe though that none of them are as important as finding someone who has exhibited a history of using good judgment. Good judgment is comprised of many things – honesty, character, integrity and thoughtfulness all come to mind. But good judgment is all of those things in action. Consistent good judgment is acquired over time. Will Rogers once said “good judgment comes from experience, and a lot of that comes from bad judgment.” Truer words have never been spoken.

Not too long ago, a board member who I’ve worked side-by-side with for years exhibited particularly poor judgment that has had significant negative ramifications for the company. He acted in a self-serving manner and placed his own interests ahead of the company. It’s very important to note that he didn’t do this maliciously. He cares deeply about the company and genuinely wants it to be a great success. Nevertheless he didn’t think through the consequences of his actions and subsequently hurt the company and wound up being forced to tender his resignation from the board.

I’m sad to say that I saw this coming. It wasn’t the first time this director had exhibited poor judgment. A handful of times over the last couple of years he acted without really thinking, only the consequences weren’t as serious. Nonetheless, I saw a pattern emerging and predicted an ending like this to other board members. The hard part is that this director was well-liked by everyone, myself included. I always enjoyed his company and he’s one of the brightest people I know. He helped the company on numerous occasions and went out of his way to do so. Nevertheless his poor judgment resulted in a lousy outcome and caused a great deal of heartache and pain for everyone involved and it could have been avoided if the board collectively acknowledged his pattern of judgment and acted earlier than later.

This isn’t the first time I’ve seen directors have a significant negative impact on a company, not by a long shot. Directors have far more influence on the success (or failure) of a company than most people think. They comprise a small group of people who ultimately control the destiny of a company.  They are responsible for keeping, hiring or firing the CEO and other C-level executives, approving the budget, raising any material capital (equity and/or debt) or issuing more shares, approving employee options, and many other important decisions. Having people who consistently use poor judgment on your board can have dire consequences. On the other hand having high-character, thoughtful directors can result in massive upside for you.

In my experience, most entrepreneurs give far too little thought as to whom they invite to serve on their boards. They see a big name and they light up thinking about the instant credibility that board member brings and all the connections he or she will make for them. Ask anyone who has served on many boards and they’ll tell you that often the bigger the name, the less work you get and the bigger the headaches. I’ve seen many board members added with very little diligence done and I assure you that’s a recipe for disaster. Most founders I’ve worked with do a great job of diligence before hiring C-level executives, few do the same amount of work before adding a board member.

So what is good judgment and how do you spot it? It’s a little bit like Justice Potter’s famous quote, “I can’t explain it but I know it when I see it.” How do you find out if a potential board member has good judgment? You invest time in getting to know people who have worked closely with them before. Talk to as many people as you can. Ask them about that person’s decision making. How does he make decisions? Is he thoughtful? It’s easier than ever (LinkedIn) to reach people who have worked with someone. I urge founders to put the same time into diligence on prospective board members as they do other key hires.

Startup CEO – The Loneliest Job

I’ve long believed that being the CEO of a startup can be one of the loneliest jobs in the world. For the first couple of years of a startup’s life (usually before a seasoned and senior management team is assembled, the CEO is looked upon as the captain of a ship in hurricane waters. Despite the constant onslaught of swells threatening to capsize the boat and send the crew to their watery graves, the CEO must remain stoic and reassure everyone on board that he’ll get them through the storm. Only in a startup, there’s not one storm, but one after another after another.

More often than not though, the CEO has as many doubts and fears as the rest of the team – only he can’t show it – the crew is looking to him for reassurance and comfort. Perhaps the CEO has a spouse or best friend that he can talk to when he’s troubled, but even they usually lack enough context or experience to really be helpful and even if they do, he knows they’re biased in their unwavering support.

Recently, I received an email (along with another board member) from the CEO of a company that I’m on the board of. The very first sentence of the email said “I’m gonna vent – it’s easier than a super composed email or waiting for the perfect time to talk and probably more true to my emotions.” Then, for a few paragraphs, he vented – not with anger – just an emotional discourse on an issue that plagues many startup CEOs. He closed the email with “This is the source of my angst right now. Rant over. Take your time responding – this is chronic, not acute. I’m looking for deep thoughts vs. quick answers.”

So what happened? The three of us brainstormed a bit about the issue and committed to working on it together, and then we went back to work. End of story. No backchannel between me and the other board member, no raised eyebrows, just admiration from both of us for a CEO that has the maturity and wisdom to reach out to his board members in trying to solve a challenging problem.

I think there’s something important to be learned here. First and foremost, this CEO has invested significant time and energy into developing a deep and trusting relationship with myself and the other board member to the point where he feels comfortable sharing all the warts of the business with us. In other words, he trusts that we know how the sausage is made.

In return for his trust and openness, he gets a couple of experienced confidants to share the challenges of growing his startup with, without fear of reproach or recrimination. In fairness, this degree of candidness might not work in every situation.  My advice for startup CEOs is to simply try moving in this direction. Your degree of success and subsequent satisfaction will be predicated on having board members (even just one) that are capable of parsing the difference between typical startup challenges and an ineffective CEO.