I am fortunate to be able to have coffees, happy hours, phone calls and walks with some really smart people. Having spent the last 15+ years working in and around the startup world my network contains investors, founders and supporters of all kinds. I started this blog as a way for me to capture the learnings I have had so that others may benefit from it (and I don’t forget them). As I move forward with this blog I also want to give readers the opportunity to hear it right from the mouths of the smart people who teach me.
So, in the coming months I will be posting a variety voices in addition to mine. the format is simple, a small handful of questions to provide my friends, colleagues, mentors and others the opportunity to share directly with you. Sorry you will have to provide your own coffee.
Don’t worry there will be continue to be plenty of my own crazy ramblings Half Baked ideas and posts of me just thinking out loud. the goal of adding these additional voices is to make sure that they’re smart messages don’t get lost in translation. I thank in advance all of the people in my network that have and will be contributing. I’m grateful for all that I’ve learned from you and hopefully I’ve been able to give a little bit in return.
When I started this blog I set out with a single goal, to become the Rick Rubin of Startups. I wrote about why and even declared it on my page to hold myself accountable. Years later I am not sure where I stand in my quest but I do know that the goal remains the same. I have had the good fortune to be counselor, coach, partner, audience to some great entrepreneurs. Founders that have consistently inspired me and always challenged me to never just phone it in.
As I close in on my 5th year in New Orleans, I took some time to look back on the some of the many startups that have been kind enough to share their journey with me. They have varied in every conceivable dimension; sector, experience, stage, and viability, just to name a few. While they are all startups and they are all founders they are also all unique.
When I first moved down here I wondered how long it would take for me integrate into the startup ecosystem. While I had over a decade of experience working with early stage companies I wasn’t from here and people “ain’t been knowing me” from high school. But the community down here welcomed me with open arms, a trait I saw repeatedly as others came to town. At the time, ground zero for the ecosystem was the IP Building. With LaunchPad, Idea Village and most importantly Capdeville under one roof, it was easy to actually see the community growing. A special thanks to Tim Williamson, Chris Shultz and James Eustis for being such great hosts during those early days.
I take coffee, drinks, walking meetings every day with founders. It is a joy to listen to stories, share experiences and solve problems. You all have taught me so much. I am very grateful to learn from, collaborate with and call you friends. So in no particular order, and in no way complete, here is a list of some of you who have made my first five years here such a joy. I look forward to the next five. To those on this list, and to other founders whose wise paths I have yet to cross, if there is ever anything I can do to make your journey better, you know how to reach me. Namaste.
About once a week someone pitches me a new idea (to them) that is being done by another company. While I don’t believe that competition is bad (it’s the opposite) or that markets can’t support more than one entrant (most end up with at least 3) I do believe that the people pitching me do not really understand what they are copying.
Too frequently, me-too startups miss the point because they only see what is visible and only at a moment in time. I had a mentor who always said that you can’t tell which way a car is moving from a snapshot. And with startups it is all about trajectory not current location. Was Uber just a taxi alternative or Snapchat a photo sharing app? While at one time you could have easily described them as such, that was just what could been seen at the time.
Startups are never “done” they are always seeking new learnings in order to change, improve, refine the value they offer. And while the word “pivot” has long since fallen out of favor and in to parody it remains the inevitable result of paying attention to those learnings. As founders we must do the same.
A friend once told me that you have to start with who you want to be “be” not what you want to “do”. Startups are the same. So the next time you look at a startup and say ” I could “do” that, ask yourself what they could “be” and see if you still want want to pitch me.
It was over 2 years ago when I was asked to judge a pitch competition being held in a bar. Since all great ideas start out as bar napkin sketches I thought that it was a perfect setting. You can see my blog post about it here. It was so well received that the restaurant, SoBou, asked me to host a weekly Friday lunch. We gathered some special guests to tell us about their entrepreneurial journey and we shared a table with liked minded founders, supporters and friends.
And so it has gone for over 24 months. We skip a week or two to honor special holidays like Thanksgiving and Mardi Gras but for the most part it is now solidly locked in my weekly cadence. Over this time the table has grown, and a core of regulars has emerged as has a wonderful parade of drop-ins. Speakers have become regulars and regulars have become speakers. And many have become friends. It has truly been a honor to share the table with everyone that has come through.
SoBou offers free wifi and 25 cents martinis, not to mention some amazing food. I have called it the best co-working spot in the city. But it is the people that make spot. Our Friday lunches have become a place to share your week with others that understand the challenges of starting a business. War stories, advice and support are always in great supply.
A huge thank you to Ti Martin for encouraging us to do the lunch, Sam Fritz for being my partner in crime every week and the entire staff at SoBou who are the most gracious of hosts every week. If you are a founder in New Orleans, or even just visiting, you should swing by. I’ll bring a quarter to buy your first drink. Learn more here.
From the time we start taking field trips in school it is etched into our head. There is a whole genre of great movies considered “buddy flix”. And if you ever meet a person named “Buddy” I would wager you are predisposed to like them. At its core the buddy system consists of the recognition that two is better than one. At some point however, in a world where individual achievement is so celebrated, the value of having someone at your side can sometimes get lost. It shouldn’t be.
I have been a long time proponent of co-founders. Down here in New Orleans I have seen a lot of single founder startups. No disrespect to the talented founders here in the Crescent City but being a founder is hard. Without a buddy it is even harder. Having a co-founder gives you someone to be real with, someone to call you on your shit and someone to hold you accountable. This is not about mentorship or coaching this is quite simply a mirror whose reflection of yourself you trust.
Since I assumed the role of CEO of VL Group eighteen months ago I have essentially been a solo founder, the very thing I have advocated against. Here is how I am coping.
Step 1: Find One
One way to do this is to look for the “no one understands me” expression as you talk to others at those painful networking events. Glance around the Meetup you are at and nod at the exhausted person at the other end of the bar. Other founders are a great source of buddies but not the only one. IMHO the criteria for this role is only what was listed above, not a mirror image of yourself, so look at who is around you right now. Here is a helpful test. If you were to explain a problem you were facing and their response would be greeted by a voice in head that says, “you don’t get it” that is not your buddy.
Step 2: Weigh Yourself In Public
Once you have found one the next step is to make sure that not only can they give you real feedback on what you do but also that they are empowered to give you shit for what you don’t do. One easy trick to get the most out of your mirror is to give them a list of questions to ask you when you meet. Have them ask you about the things that are important to you. WeightWatcher’s differentiator for the longest time was the peer weigh-ins. The peer accountability was the key to results and it is the same with me. My buddy asks me a series of quick question when we talk. Mine are about how I am taking care of myself, what I am reading, and if I am writing (yes, are you reading this?). These are things that I said were important to me and having to answer these questions out loud won’t let me forget it.
Step3: Be One!
The role of buddy is and important one and in the spirit of paying it forward you should be one. The best way to understand the value added by having one is to find a friend, hold them accountable and applaud when they achieve their goals.
“Victory has a hundred fathers and defeat is an orphan.”
When I saw the article from Technical.ly today on the “reinvention” of Delaware I was at first buoyed with pride for my one-time address. That quickly faded as I realized how the founding story has been reinvented as well. I was especially struck by the fact that at least one of the authors knows better, much better.
As background, I starting working in Delaware starting in late 2001 following the dot com bust and moved to Wilmington in 2006. I worked with the people in the article and attended some of the events. I also pitched them to help out startups early on and helped introduce Technical.ly to some of them. This preamble is to say that I was there. I also want to say that I am not invalidating that there were many forces at play to make it all come together. What I am saying is that if you think the recipe for success for your startup ecosystem doesn’t include crazy, disrespected, marginalized, non-establishment, non-authorized characters YOU ARE WRONG.
A polarizing outsider whose investment often limited others’ participation. But when there was no investment capital in the state who formed the first home grown fund? Established in 1995, the Delaware Innovation Fund was the state’s first venture-capital firm. Freschman started the fund at the request of Delaware’s then governor, Thomas R. Carper. Combined with Early Stage East, his annual conference, it was a spark. David and I butted heads more than once. He style was direct and he always played bigger than he was. Characteristics I have come to respect. His legacy, and I hope the attitude, continues on in Delaware, in the person of Pedro Moore. Probably considered not as qualified by most, but isn’t that where the best surprises come from.
GO SEE FOR YOURSELF
I covered a whole lot of other examples, two plus years ago, when I wrote my founding story for Delaware’s startup scene. You may see some names there they you haven’t heard of. That is my point. Add to it the amazing supportive culture that allows people to create powerful podcasts, social change programs and a feeling that its OK to ask for help and you have a taste of it. But know it is just a taste. Go see for yourself. See the founders, innovators and others that are there…after all the rest have commuted out of town. And buy a T-shirt from Spaceboy because I am done giving them out.
I have a saying, “the lifespan of a mentor’s advice is the same as milk.” In a world that is moving as fast as as ours is, what worked last year is highly unlikely to work this one. It is only those who constantly seek to have new experiences who can have lasting value to those that they advise.
Time on the Bench
I have been fortunate enough to hang around the startup world for two(?) bubbles and close to two decades. I have been the person writing checks, helping others get checks and working with founders fix problems that checks don’t. I have spent countless hours on in coffee shops, bars, conference rooms and airplanes talking to founders and offering whatever perspective, experience and advice that I could. I have no illusions about the wisdom that I “dropped”. All I can hope is that it was a net positive.
For the last 14 months I have gotten myself back into the ring. Yes, I know I shifted my sports metaphor, but I really don’t care and if you think that growing a company is not similar to getting punched in the face then you haven’t done it. As CEO for VL Group I have become the very leader that I have been advising; passionate, idealistic, visionary, action-focused…and stupid. Really.
One of my most recommended authors is Ryan Holiday. His two books, The Obstacle is the Way and The Ego is the Enemy, are now on my annual re-read list. In Obstacle he outlines three core pillars; perspective, action and will. As mentors we often focus on the steps that our mentees need to take (action) or how they should be prepared for a marathon not a sprint (will). Sometimes we forget that our very perspective is different from theirs. This is a benefit but also a curse. It is easy to suggest cutting features from a MVP when you hold no emotional attachment to them. It is fine to suggest a team change when you haven’t spent weekends working with someone to make the company come to life.
As mentors we should really all work to remember the perspective of the founder. Like an Instagram filer it is is easy to remember our times as founders and business leaders in a more beautiful way. Building a business isn’t easy and it isn’t pretty. Remember firing a friend, being embarrassed in your community or having your mortgage company call? Now talk to a founder about why they didn’t have time to build a pitch deck or build a financial model.
I am fortunate to have known the pool which I chose to jump into the deep end of. Many don’t. Being a player (not in the rap “you go playa” sense, just in the continuing sports metaphor sense) has reminded me how I can be a better coach. Perspective, the founder’s, can almost always be a better place to start than from yours.