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.

Financing Round Nomenclature Revisited

When I started investing in startups a long time ago, the labeling of financing rounds was as simple as the Sesame Street alphabet song – A is for Abbey, B is for Bert, C is for Cookie Monster; ok, you get it. The rounds were named for the purpose of identifying shareholder rights in a particular class of stock. The names weren’t used as a tool to avoid pigeonholing a startup into a particular stage of growth the way they are today.

The labeling of financing rounds has become silly: Seed. Pre-Seed. Early Seed. Gap. I’ve even seen a round classified as “Genesis” recently. To compound things, if you ask a dozen entrepreneurs or investors what each of these rounds mean, I guarantee you’ll get a dozen different answers.

I’ve come up with an idea to simplify this practice and ran it by a few friends. They all liked the logic and simplicity, so I’m throwing it out there. I propose that we start labeling rounds by the size & post-money valuation of the financing. Here’s a hypothetical financing history of a company using this method:

$500K/20% Discount Note round.
$750K/6.5M round.
$3.2M/17.8 round.
So on and so forth.

Using this process, when I look at the cap table as an investor, it tells me in an instant just about everything I need to know about a company’s financing history and eliminates all the nonsense about trying to properly name a financing round.

Whaddya think?

A Beautiful Continuum

The first time I met Natty Zola was in the old Techstars bunker back in the summer of 2009. He and his co-founder Nate Abbott had recently started a company called Everlater and were going through the Boulder Techstars program. They told me their story about chucking their Wall Street jobs, traveling around the world together and moving back home to Boulder (where they’d been best friends since kindergarten) to start Everlater.

The origin story of Everlater (anagram for Traveler) was that Nate and Natty grew frustrated during their travels that there really wasn’t a good platform to share travel experiences in real time with friends and family back home. They taught themselves how to code, built an elegant site which encapsulated areas for journaling, photos, maps etc., and started building the company.

I knew during our first meeting that I wanted to invest. Their enthusiasm was infectious and Natty & Nate were learning machines. The experience of being involved in building Everlater with these two is one of the truly memorable and gratifying chapters of my career. Ultimately, AOL acquired the company and Nate & Natty took on senior product roles at Mapquest. Here’s a fantastic short video of their journey from inception to acquisition.

Two years ago, we were looking for a new Managing Director of our Techstars Boulder program and Natty immediately jumped to mind. He’d been through the gauntlet as an entrepreneur, spent a few years at a large tech company working on product, was born and raised in Boulder and most importantly, he’s an incredible human being with a huge empathy gene. It was the perfect choice and we couldn’t be more thrilled to have Natty running the Techstars program at our original location.

We encourage all of our Managing Directors to become board members or observers at some of the companies that graduate from their classes. As fate would have it, Pana (an incredible on-demand mobile travel agent) went through one of Natty’s classes and recently Natty joined their board of directors. His experience in the travel industry is the perfect fit and Natty’s now in the ideal position to mentor founder Devon Tivona. Where the continuum comes full circle is that Devon was a summer intern at Everlater.

At the 2005 Stanford commencement speech, Steve Jobs said something that’s become my favorite quote of all time.

“You can’t connect the dots looking forward you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something: your gut, destiny, life, karma, whatever. Because believing that the dots will connect down the road will give you the confidence to follow your heart, even when it leads you off the well worn path.”

When Nate called Natty back in 2008, urging him to quit his high-paying Wall Street job and come join him on the adventure of a lifetime, little did they know where it would take them, but something in their gut told them to trust the universe and just do it. Nate’s gone on to become the Product Manager of Airbnb’s recently announced Trips and together, he and Natty can now look back and connect the dots that brought them to this point in their lives.

Hacking Reference Checking

We all acknowledge the critical nature of thorough reference checking as it relates to hiring or investing in someone. However, given that most people are reticent to offer a negative reference, most of us struggle with extracting the type of valuable feedback we’re seeking in order to make better decisions.

Many years ago, a mentor of mine shared a hack for reference checking that I still use today. For me, it still delivers more signal than any other method I’ve come across. Here’s how it works:

Dear Samantha,

I’ve discovered that you worked with Daniel Jones at DKR a few years ago. I’m evaluating an investment in Daniel’s new startup and I’d be grateful if you’d be willing to share some insight with me about your experience working with him. However to be respectful of your time, I’m only asking you to follow up and reply to this email if your experience with him was exceptional.

Thank you, Mark

We all want to hire or invest in exceptional people. Well, anyone who’s had a terrific experience working with someone will be happy to reply to an email like this, right? Mediocre or less though and they’d probably rather go to the dentist. As you can see, this method allows people to gracefully opt out of those uncomfortable calls while at the same time, delivering the signal you’re looking for. The most important aspect of this approach though is to send at least 10 emails like this, even more if possible. The more data points, the better.

I’m always thrilled when I get a bunch of responses with people telling me that they’d be more than happy to tell me how great someone is and how I’d be foolish not to work with them. On the other hand, a handful of non-responses is a sure sign that I’ve got some more diligence to do.

Give it a try and let me know how it goes. I’d also love to hear about any other methods people use to make better human capital decisions.

The Music Never Stopped

“Music is a moral law. It gives soul to the universe, wings to the mind, flight to the imagination, and charm and gaiety to life and to everything.” – Plato

Back in 2011, I walked into Topspin Media’s office for the first time and this bearded dude in a faded brown tee shirt popped out of his chair, and with a big smile stuck out his hand and said “Hey, I’m Bob, you must be Mark.” So began a special friendship which culminated in our announcement yesterday of Techstars Music and I couldn’t be more thrilled to welcome Bob Moczydlowsky to the Techstars family as Managing Director of this incredibly exciting new program.

So first thing’s first. Music as a business? Let’s face it, it’s been a difficult industry for startups to succeed in. Actually, it’s been brutal. I learned that as an investor in Topspin where Bob, Ian and an insanely passionate and talented group of people created a company that was genuinely disrupting how artists connect with their fans. Yet we lost money in that investment. Simply put, the dynamics of the industry have historically made it difficult for startups to scale.

So why are we placing a bet on a rock pile where so many pick axes have been broken? Well, let’s start with the fact that more people listen to music every day than log into Facebook. Music is unlike anything else, it’s the cultural scaffolding that unites people from all walks of life. It completely transcends socioeconomics and touches every human being in a deeply unique and personal way. However, from a business perspective, the music industry is underinvested in for good reason. Less than 2% of mobile ecosystem dollars goes to the music industry and yet the average mobile user consumes close to an hour of content every day. There’s opportunity there!

We recognize that it’s going to be hard, but for the first time in history, we’ve been able to bring some of the most important players in the ecosystem together to collaborate and we’re willing to take a stand and say hey, this is important and we’re going to do this. There’s new technologies and business models emerging, as well as new delivery & consumption paradigms which lead us to believe the industry is at a tipping point.

We’ve wanted to do a music accelerator for a long time, but believed that the key to doing it well would be a consortium model where the most important players in the ecosystem were deeply engaged. That’s a tall task given the historic dynamics in the industry and there’s only a few people that could pull something like that off. Bob’s one of them. He’s universally liked and respected in the industry and that’s rare. He’s also grinded away in startups himself so he has a deep and genuine empathy for founders – perhaps the single most crucial characteristic we look for in our Managing Directors. More than anything though, like all of us, Bob never stopped being a fan. Take a moment and watch his brilliant TED Talk, Think Like A Fan.

Most importantly, there’s no way we could possibly attempt this without the leadership and forward thinking of our partners in this endeavor. I’m blown away that Warner Music Group, Sony Music, QPrime Management, Silva Artist Management, Era of the Engineer, Harmonix Music Systems, SONOS & Bill Silva Entertainment all came together to partner with us. It’s really hard to get your head around the breadth and depth of mentorship & access these startups are going to get.

There will be a lot more information in the coming weeks. LA is the perfect place for us to do this and we’re seriously stoked to launch another program in one of the most important and fast-growing startup communities in the world. Techstars is absolutely #LongLA. For startup founders who would like more information about the program or how to apply, please contact [email protected].

Finally, if you’re wondering why there’s a big Stealie on top of this post, that’s simple. I’m a deadhead from way back and I’ve been waiting a long time to use one in a post. Seems like the perfect moment.

There’s a band out on the highway
They’re high-stepping into town
It’s a rainbow full of sound
It’s fireworks, calliopes and clowns
Everybody’s dancing…

This Is What The Apocalypse Looks Like?

Back in Q1, you couldn’t swing a dead cat without hitting someone advising startups that the world, as they knew it, was coming to an end. Venture dollars flowing to startups had decreased from $16B in Q3 ’15 to $12B in Q4 and VCs were telling anyone who would listen that nuclear winter was in sight and funding would be drying up. The media just ate it up. Take a look at just a tiny sample of headlines from early Q1.

apocalypse

Imagine my surprise when I opened PWC’s VC Q2 Money Tree report on Friday (ok, I’ll admit that I wasn’t surprised at all). Take a look at the chart from their report below. Not exactly the apocalypse everyone was predicting, right? To be fair, while dollars have increased again, the number of deals fell by about 5% (suggesting that larger dollars were going into some later stage companies).

Q2 16

I wrote a post about all this in February and my advice to founders remains the same as it always is. Raise more than you think you need. Price your rounds to avoid the pain of stacked notes. Watch your expenses. But whatever you do, don’t pay attention to what anybody’s saying about the macro because they’re all full of shit.

Will the funding environment get worse for startups? Yes, of course it will. Eventually. Bill Gurley’s been telling us we’re in a bubble for years now. He will undoubtedly eventually be right. But there’s also logic supporting the notion that an entire generation of globally important companies will be born and go public by the time he is. We’ve now had ten quarters in a row of over $10B of venture capital flowing into the system. Venture Capital firms raised more money in 2014 than ever before in history and then they raised even more in 2015! All of those firms have a mandate to put that capital to work which means VC dollars will continue to flow liberally to startups at least for the next 3-4 years.

My $.02? I think we’re in the greatest tech innovative cycle in history and capital will continue to be available to fuel it. Technology is solving more problems for more people in more ways around the globe than ever before. I see it when I travel to our 24 Techstars accelerator programs and the hundreds of events we put on for entrepreneurs around the world in over 130 countries. Barring a global economic collapse (which certainly does seem like better than a zero percent chance given the events of 2016 and the potential fallout from our Presidential election this November), I think we’ll continue to see a healthy environment for startups for years to come.

Finding Obsession in Iceland

A few weeks ago, I was fortunate to spend two weeks in Iceland, a country I’ve long wanted to visit. My trip began with Startup Iceland, the annual event run by my friend Bala Kamallakhara. It was a terrific few days, starting with the launch of Ultrahack on Sunday night. On Monday, we were treated to opening remarks by the outgoing President of Iceland, Ólafur Ragnar Grímsson who had been in office since 1996. He delivered an impactful talk about how technology has transformed society since he took office (while Bill Clinton was President). It was a real honor for me to meet a sitting President. Bala assembled some captivating speakers including Hjalmar Gislason, VP of Data at Qlik who shared his experiences scaling a startup to scaling a product for a NASDAQ company. We also heard from Magnus Bjornsson, Sr. Director of Development at Oracle which acquired Endeca, the startup where he headed up engineering. Among many others, I was really stoked to watch Techstars CTO Jud Valeski give a great talk on data and equally excited to have Techstars Managing Director Jenny Fielding join me and Bala for a fireside chat about the impact of the global accelerator movement. We all spent the next day at Reykjavík University working with a bunch of terrific startups.

Bala – the entrepreneur leading Iceland’s startup community

I left Reykjavík the next day in a 4WD with Jud to do some exploring in the sparsely populated north highlands. As we bounced around the dirt roads, we spent a lot of time talking about how inspiring it was to see another entrepreneur-led startup community unfolding. Bala has adopted Brad Feld‘s Startup Communities as his blueprint and it’s easy to spot the familiar pieces falling into place that will surely make Reykjavík a city that’s going to produce its share of important startups for years to come.

I finished my time in Iceland by fulfilling a dream to spend a week side-by-side with my friend Chris Burkard, who many believe to be the most inspiring outdoor / adventure photographer in the world. If you’re unfamiliar with Chris, check out his Instagram feed or better yet, take a few minutes and watch his incredible TED Talk and you’ll see why he’s motivated so many millions of people to spend more time outdoors. We spent a week with a small group of passionate photographers exploring the remote Westfjords. The highlight for me was an absolutely epic hike from 6pm to 6am in the Hornstrandir nature preserve on the northern tip of Iceland, where I captured this shot of Chris somewhere around 1am.

Chris

While the week was truly remarkable and I learned so much, the most inspiring moments of my time with him occurred on the drive back to Reykjavík at the end of the trip. Instead of taking the 30 minute flight we had booked or a 6 hour drive on the highway, Chris decided we should drive through the most remote single lane and dirt roads in search of more great frames to shoot. We jumped in a Defender with his assistant Ryan in Ísafjörður and set out on a 24 hour adventure which crystallized for me why Chris has reached the pinnacle of his field.

For context, remember that none of us had slept for more than a few hours each day for the previous week as we were in the arctic circle and the sun never dipped below the horizon while we explored the remote fjords by sailboat. We’d set out on hikes over the fingers of the fjords each “night” and Captain Siggi would pick us the following morning. We’d hike for miles and miles, stopping to take advantage of the golden light created by the sun sitting on the horizon from about 9pm to 3am.

So despite (or perhaps as a result of) some pretty intense sleep deprivation, Chris decided that we had 30 hours left in Iceland and we were going to milk it right up until we stepped on the plane. We filled up with gas and coffee and took off in search of great features to shoot that Chris had been researching. I learned how Chris leaves little to chance. He does a bunch of research about the places he visits and stores the coordinates of everything he wants to photograph in his phone. The weather turned cold and damp and armed with a series of GPS coordinates and a map, we drove for over 24 hours, stopping only for beautiful photography opportunities or to warm our bones in remote hot springs.

My biggest takeaway from that journey with Chris was how completely obsessed he is with his work. Despite the fact that we had just spent a full week shooting and talking about photography incessantly, he was in the zone the entire drive. 24 hours without any sleep! While the weather worsened and it got colder and colder, he never lost his enthusiasm. We’d reach our coordinates, pull over and he’d photograph something from every angle. After a while, I’d find myself heading back to the truck to warm up and Chris would be out there with cold wet fingers trying to capture the perfect shot. After a storied career, 25 trips to Iceland and millions of photographs taken, he’d get back in the rig and with the enthusiasm of a kid at Christmas talk about contrast, and light and what Iceland means to him.

Chris during our 24 hour adventure

Gazing out the window on the flight home, I couldn’t stop thinking about how similar Chris is to the most spectacular founders I’ve ever worked with. People like Isaac Saldana of Sendgrid, or Ian and Adam of Sphero or Brad Schell of @Last Software who turned their obsessions into some of the most important companies in their respective categories. I’ve had a front seat in watching how my partner David Cohen has seen his obsession with helping entrepreneurs emerge into the worldwide movement of #givefirst which is redefining how mentors and companies interact with startups. Whenever I’m asked what the common characteristics of the best entrepreneurs I’ve ever been around are, I always begin with the obsessions which drove them.

It’s trite to try and articulate how challenging it is to rise to the top of any pursuit, whether it’s photography, sports, music or building a startup. Only those who have a healthy obsession make it to the top. That’s why more than anything else, I personally look for entrepreneurs who have a serious obsession about solving a problem. There’s so many obstacles to success that if you’re doing it for any reasons other than a very real obsession, the difficult periods will likely derail you. Passion’s not enough. Discover your passion and do it on weekends. If there’s a big enough problem that you’re truly obsessed with solving (I like to define obsession as the thing that makes you forget to eat and poop), give me a call and let’s talk about the startup you should be working on…

Some Gray Haired Insights For New Investors

There’s been a flurry of posts so far in this new year advising startups how to deal with what certainly appears to be the beginning of an inevitable market correction (based upon your point of view, feel free to substitute your flavor of panicked adjectives for “correction”). It seems that every VC who blogs is warning that winter is coming and cautioning CEOs to store their acorns and cut back on their burn rates. All good advice.

I haven’t read much though about how to prepare for this if I’m a relatively new investor in startups. There’s a whole new breed of investors (both angel and new VCs) who have been actively investing in startups since 2010 (when we emerged from the last major recession) who have never been through a downturn as an investor. I’m writing this specifically for their benefit as I’ve been around long enough now that I’ve experienced multiple full economic cycles as an investor and started my career working on Wall Street during the crash of 1987. I’ve got a few more gray hairs today than I did then and I know some of these insights would have helped me better weather those.

To begin with, what does the trajectory look like? At the outset, term sheet valuations start contracting up and down the venture capital food chain and then they start drying up from the growth investors (except for the most compelling opportunities) as they decide to sit on their hands for a while and figure out how bad things really are. Most of the early-stage investors are still investing at this point as by nature, they’re generally a more optimistic group. I think it’s fair to say that we’re somewhere in the middle of this stage today. If the downward momentum continues, startups begin losing lower tier customers and missing their numbers. After the early stage investors start seeing this across their portfolio, they too get spooked and begin to and begin to slow their investment pace. The slide continues and soon portfolio companies are losing some of their best customers. This is when even the most optimistic investors start putting their wallets away for new investments and start asking themselves “what do our reserves look like?”

A few more months pass and eventually, large corporations begin laying off thousands of people at a time. Each time investors step on the treadmill at their health clubs, they’re greeted with flat screens showing clips describing another massive layoff. That’s when folks realize that shit’s gotten real and fear sets in. Not only are very few new venture investments getting done, but the partners at VC firms are now spending the bulk of their time working with their portfolio companies figuring out how far back to yank on the expense lever. Eventually things get bad enough that one of the top venture firms decides that we’re on the path to hell and there’s no turning back. That’s what happened on October 10, 2008 when Sequoia published this infamous deck. Pay particular attention starting on slide 41. At this point, vc partner meetings are spent discussing among themselves which of their portfolio companies they should allocate dwindling reserves to (“live”) or not (“die”).

Admittedly, nothing I’ve shared yet is particularly enlightening or helpful. Anyone who’s lived through it is probably nodding their head in agreement. Here’s where some valuable insight for new investors can be gleaned. Did we continue on the road to hell after Sequoia pronounced that we were at the gates? No, of course not. In fact, it was only three weeks later on Halloween 2008 that we reached the market bottom in the NASDAQ.

ripgood

Anyone reading this who’s remotely familiar with the public markets has learned that it’s impossible to time market tops and bottoms, but you’ll be amazed at how many smart and sophisticated private investors were so spooked by Sequoia’s pronouncement, that they didn’t invest in any new companies for a very long time afterwards. I’ve even heard conspiracy theories that Sequoia intentionally sensationalized the deck to clear out investors so that they had to pick of the litter for a while. Unfortunately, those investors who throttled back missed the best pricing of startups in the last fifteen years. Even more importantly from my perspective, the “wantrepreneurs” had all gone home and none other than the most steadfast, determined entrepreneurs were starting companies at that time. In other words, the founders we as investors all dream of working with were the only ones starting companies! What I’ve learned through experience is that the very best entrepreneurs don’t pay much attention to the gloom and doom everyone else is paralyzed by. They see a pain point, they envision a solution, and they set out to execute against it. Sure, how they go about it changes, but they generally ignore what’s going on at the macro level. Finally, because they’re solving real problems, they let customers finance their early growth.

A great example of this is Isaac Saldana, the founder of SendGrid which he started in November 2008, just weeks after “RIP Good Times” was published, at the very bottom of the trough when things looked their bleakest. Isaac knew deep down that he had figured out a solution to an important enterprise problem and he didn’t wait for the lifeguards to say it was safe to get back in the water to start his company. He left his job and founded SendGrid when everybody else was running for cover. Today, Sendgrid is arguably the most important email infrastructure company in the world.

I remember a series of conversations I had with Brad Feld in 2008 about his perspective on investing through various parts of economic cycles. Brad was (and is) resolute in his belief that creating outsized returns in the venture industry demands ignoring the macro environment as it relates to investment pace. I vividly recall those conversations which helped give me the courage to lead financings in companies like SendGrid, Purch and Cradlepoint in 2009 when most venture investors were sitting on the sidelines. All three of those companies are worth hundreds of millions of dollars today.

Are we entering a minor correction? A downturn? A sustained recession? Truth is, no one really knows. One immutable truth of investing though, is that you can’t time the markets, be they public or private. What’s the biggest lesson to be learned here? Invest the same amount of capital at the same pace, year in, year out. That means don’t get greedy when prices are low, and don’t sit on the sidelines when prices are high. Investing in startups sits on the riskiest edge of the investment scale. By investing the same amount of capital in the same number of companies year in and year out, you prevent yourself from being whipsawed and having too much money invested at market tops and not enough money at the bottom.

One last piece of advice for those who have only been investing in startups since 2010. If this slide continues, it’s not going to be fun. It simply sucks coming to work every day for months or even a couple of years and deal with shitty news. Whatever you do, remember to keep this one thing in mind though. Never forget that you’ve got a portfolio of investments and that despite the degree of carnage, many are going to survive and ultimately thrive again. Now put yourself in a startup CEO’s shoes. They’ve got one egg and no basket. They’re all scared and other than the most experienced, they really don’t know what to do. You may not know either, but having somebody else in the foxhole goes a long way. Practice empathy. Spend more time with the CEOs you’ve backed and do everything you can to make their lives easier. You’ll both survive the winter and emerge with a bond that lasts a lifetime, well beyond the inevitable thaw.

Act Like You’ve Been There Before…

Recently, I saw someone share a tweet from a young, aspiring VC who posed a GIF on Twitter depicting an irreverent character in an effort to share his frustration that investors aren’t keen to invest in first time managers. My first reaction was to chuckle as it was indeed pretty funny. My second reaction was to think, “kid, you don’t get it yet and you probably need a mentor.”

There are two short takeaways for entrepreneurs from this. First, that young VC was partially right; LPs don’t invest in first time managers, that is until until they do (they just don’t do it very often). There’s been thousands of venture firms created over the last fifty years and I’ll bet there’s been a hundred started in the last two years. Somebody’s gotta be funding those first time managers, right? Create a compelling enough opportunity and someone’s going to invest.

The second takeaway is very simple. Every single LP I know tracks new and emerging managers on social media. What do you think happened to this young VC’s stock when they saw that post? Think they said to themselves “hmm, here’s someone I want to track?” Nope, me either. I’m sure some LPs probably stopped following him then and there. Always remember that all investors (angels, VCs & LPs) use social media to try and get a better feel for people they’re interested in potentially investing in and if you don’t think they’re they’re paying attention to what you’re posting in your various streams, you’re not just naive, you’re dumb.

Founders, rest assured that investors are paying attention to your social behavior. Don’t put anything out there that you wouldn’t feel comfortable saying to them in a meeting. Social media represents an incredible tool to allow people to get to know you better. Use it wisely. One of the top LPs in the country recently told me that he seeks to invest in people “who are better versions of himself.” Investors want to invest in others that they trust and believe will be good stewards of their money. As the immortal Vince Lombardi one said, “When you get in the end zone, act like you’ve been there before.”

Who Benefits From Your Success?

Since I started mentoring at Techstars back in 2007, I’ve sat and talked with hundreds of founders trying to raise seed rounds and I’m often left scratching my head at the lack of strategic thought that goes into figuring out who to pitch. Most founders defer to attacking a list of known investors with little or no thought given as to what motivates those investors, what excites them and what sectors they understand. They wind up competing with every other startup in their community trying to raise capital at the same time. I learned a long time ago that trying to raise capital from people who A) understand the industry you’re trying to disrupt, B) benefit at some level from your success or C) at least have some emotional connection to you is far easier than pitching investor after investor that you first have to educate about your market and somehow must create some trust and common ground in a compressed time period.

I started learning these lessons when I became a stockbroker in the early 90s. After a month or two of training at company headquarters on Wall Street, us rookies were expected to hit the phones and start “cold calling” 10 to 12 hours a day, every day, to get meetings with strangers and convince them to let us manage their money. It didn’t take me long to figure out that I needed something to differentiate myself or this was going to be a short-lived career (which it actually was as I moved into venture investing in 1995 but I digress). I was living in Boston and decided to buy the heavy bound books from my university and my fraternity consisting of the names, addresses and phone numbers of every alumni, sorted by state. I sat down with a highlighter and highlighted every single name of an alumni within a hundred mile radius of Boston. I developed my own script leaning heavily on that one sliver of a connection and lo and behold, my appointments grew by orders of magnitude. Then, when I sat down face-to-face with them, I spent as much time as I needed to build a connection revolving around our school or our fraternity. It was only after I felt that connection did I allow myself to start talking about stocks, bonds, and wealth management. You would be floored at how many successful people began giving this kid a chance to begin managing a portion or all of their wealth because I created an emotional connection with them.

Let’s get back to fundraising. First, who should you pitch? When I started raising capital in 2000 for our first fund ($25 million) at Highway 12 Ventures, I began with the usual institutional suspects. It only took me a few meetings to figure out that we were not what they were looking for and I quickly shifted gears based upon the lessons I learned above. I had just moved to Idaho and as you might imagine, there weren’t many alumni from my east coast roots living there. So much for that strategy. I switched gears and thought, “who would benefit from Highway 12 Ventures’ success?” I started meeting with people from local institutions and business owners who would benefit from having a more vibrant startup community, and painted a picture of how beneficial our success would be for them. Once again, a dramatic increase in the quality and the success of the meetings.

These lessons are easily applied to raising money for your startup. Selling software to make doctor’s lives easier or create greater efficiencies in hospitals? Pitch doctors, not people who made their money in real estate. Is it easy to get meetings with doctors? Probably not. But I’d sure as shit figure it out if I was in that position. Got the next great solution for enterprise HR? I assure you, there’s hundreds if not thousands of senior HR execs who could write a check for $50k. Easy to find them? Nope. But I promise you that with some effort, you can. It’s never been easier to have a conversation with somebody that you’d like to. Tools like LinkedIn, Conspire and hi def video didn’t exist when I was raising money earlier in my career. With a little bit of creative thought and a good deal of effort, any founder can talk to many potential investors who understand the problem you’re trying to solve with your startup and/or would benefit from its success. You’ll be amazed at the difference in the tenor of your meetings. Founders put such Herculean efforts into building remarkable and unique products yet so many of them attack fundraising with little or no strategy. If your startup is genuinely solving an important problem, I promise you that there are many people out there willing to invest in that problem being solved. Start thinking creatively about how to find those folks and get in front of them.

Lastly (and in my opinion and most importantly), There are many so many perceived reasons why people invest in startups, but it really comes down to one thing. Emotions. Even folks like Brad Feld and Fred Wilson only invest when they find a quality in a founder that touches them deeply. Something personally meaningful. In order for your story to resonate with someone, you have to touch their heart before their head. If there’s one thing to remember when sitting down with a potential investor for the first time it’s these words from Maya Angelou – “I’ve learned that people will forget what you said, people will forget what you did, but people will never forget how you made them feel.” After 20+ years of raising capital and helping people raise money for their startups, I still believe this is the single most important ingredient to successful fundraising. In fact, it’s so integral to that it deserves its own post. Stay tuned…