Month: May 2018

  • Video Brain Dumps, Just Tell Me Where

    Writing is hard and takes a long time, but it’s worth it.

    I have found a lot of joy and satisfaction attempting to post 1-2 times per week since I launched this site in early March. My goal was sharing useful insights or things I’m passionate about that are hopefully relevant to my experience.

    I’ve gotten busy though and I’m finding it hard to hit the 2-plus-post-per-week mark with any regularity.

    Many times in working with founders or colleagues, I’m answering the same questions or solving similar problems, which in turn, spawn the idea for a useful post topic. But unfortunately, that post then becomes a much longer post or sits half-finished. There are a bunch of these I need to finish and publish.

    I was thinking about how to potentially scale the frequency of commentary on useful topics which can be leveraged by those looking to augment their playbooks on this site…. how do you alleviate the time overhead from the necessary structural perfection of the written word?

    Oh wait. Yeah. I have an idea I saw somewhere…

    So there is this thing called video and you can host it on YouTube for free. I bet that would work.

    Also, it’s always way more fun when I can answer a real questions vs post something I have a hunch will be useful to others.

    What are you working on and how can I help you? Hit me up. Best questions win.

    I’m most passionate and knowledgable on:

    • startups
    • brand building
    • consumer businesses
    • leadership
    • scaling
    • personal development
    • RevZilla-related or not
    • how, what or why topics

    I probably won’t yell a spastic intro, wear the blurple shirt or forget to breathe – that’s reserved for moto gear.

    Post a question via the comments, social media or contact me link in dropdown above. My hypothesis is that I can be more useful, more quickly, more frequently via a video response here and there. If it sucks we’ll take it down, stop or try something else. God bless the Internet.


  • Crypto Madness From the Cheap Seats

    I can’t tell you how many conversations I have had in the last six months about cryptocurrencies. It’s mainly Bitcoin, but these conversations are happening within my friend and family circles now. Yes Grandmom, it probably got the most out of hand with you over lunch. I‘m glad I talked you out of your day-trading plans before the December crash (and subsequent series of crashes).

    I do have a strong opinion about the topic, however. I believe that while the currencies themselves have garnered public attention, the underlying technologies have certainly not yet hit their stride.

    That said, here is a bit of personal texture I can share that has allowed me to land at a place of informed crypto opinion, although I would by no means call myself an insider or an expert.

    Crypto Past

    Crypto first hit my radar about 5 years ago via the VC blogosphere. It’s been a fun bottoms-up evolution through the eyes of progressive, early-stage VCs with their focus on the future.

    Late 2013, announced it would be the first retailer to support Bitcoin at checkout. That fall, we (RevZilla) entertained trying to join the race to plant the “first” flag for publicity’s sake, but ultimately stood down when ”the O” implemented in early 2014. The subsequent press and novelty were captured, leaving only the volatility of a new tender type for the next implementers. 

    About 18 months later in July ‘15, we experienced a legit DDoS attack. Right in the middle of our M&A rodeo, RevZilla went down. Not the time for the site to lose days of revenue and miss our projections, so cooler heads pointed to quickly paying a few thousand in BTC to ensure the site came back up and the threat was quickly eliminated. Even post Q1 ‘18 crypto correction, the few thousand in BTC we paid is still worth a few hundred thousand dollars, now.

    The Internet hostiles honored their promise. The site came back and we went back to the joys of ibankers and lawyers. One BTC stayed at around the $200-300 mark for a while, so I never really thought about that attack until things started going bananas in 2017. It would have been a hell of a silver lining if we would have bought some extra BTC in ‘15 and forgot about it for a few more years.

    A year later in June of 2016, I was out golfing with my buddy, a fellow tech founder, when I asked him where he acquired his Cuban cigars.

    He mentioned a few rogue sites would ship from Switzerland, had great reviews and only took Bitcoin at the time. So I opened a coinbase account and bought a few BTC at $590 to buy some cigars. With a coinbase account open, I also bought a handful of Ethereum and Litecoin, just to be a nerd.

    Weeks later, the Swiss site started taking Visa, which was super easy, so the purchased crypto then sat forgotten on Coinbase, where it still sits today (not so forgotten).

    Crypto Recent

    Next, fast forward to the spring of 2017 when things were already a hot speculative mess in the crypto world. A close friend’s son had bird-dogged us the opportunity to deploy capital to the first crypto hedge fund, called Polychain, which has early access to ICOs and load balances its risk profile across multiple (aka “poly”) coins over time.

    I got in around the end of Q2, knowing that the early investors that got in 3-6 months previous had had quite the ride. For frame of ref, BTC was at $2500 when we closed, but had been about 900 bucks just six months prior.

    In December of 2017, I thought Crypto Kitties was hilarious so I spent some ETH to buy and breed a stable of overpriced and hilarious crypto collectibles (Tomagotchi cats that you can sire). I then gave them to the people I cared most about and usually buy normal holiday gifts for, at the end of 2017.

    You can see my current  stable here, along with cats I gifted here, here and here. I’ve already “cooled” on this and the only real joy of ownership came from personally naming the cats and trolling my friends with them. Still no crypto utility besides laughter and the joy of speculating (gambling?). #responsibleinvesting

    However, it was telling to see how the ETH network struggled under the load when Crypto Kitties were at their peak, highlighting potential early scalability issues with blockchain tech. Even more interesting that Union Square / Fred Wilson has formally invested in the digital pets in Q1 of ‘18. Would love to know how that round was valued…

    Lastly, in the first quarter of this year the opportunity to follow on into a new early-stage venture extension of the crypto hedge fund became available. While the risk profile and return math on VC funds are  distributed logarithmically, it’s still very exciting to have potential access to greenfield opportunities on a new digital protocol layer. This represents a contrast to most internet investing in the last two decades, which has been done at the application layer. Obviously I’m hoping performance will be more congruent to the VC funds of 2004 and beyond vs 1996-2000, but there is a good chance we’re all still too early.

    I’m certainly curious to see when the tokens will stabilize over time as an asset class and how regulatory measures will continue to affect things, including the tax implications instituted in the new 2018 tax bill. For the foreseeable future, I’d imagine, it will certainly carry an early-stage risk profile. Again, I’m long on the sector so, at present I’m not expecting much in the near term.

    Crypto Future

    So all in, I have some texture on this and have an opinion (guess) on where it’s going. Keep in mind there are way more savvy analysts out there covering it way more closely than I. You can read about all of this ad nauseum. Just Google it. Here are my answers to the common questions that have frequently come my way.  

    • Do you think BTC and other large cap cryptos (ETH, LTC) are toast after this last correction / crash? No, but define toast. With the speculative nature of this and the fact that so many non US markets are driving it – and people are hoarding it like gold – I would not be surprised if we see levels flirt back up over 10k BTC for periods, but I can’t see another q4 run up like last year. The masses have wised up – or got hosed – at this point. Disclaimer: I’m not giving investment advice here, I’m just a dude guessing at the future along with everyone else. Don’t go buy crypto assets with any money you can’t afford to lose!
    • How are people valuing crypto to command such prices? They are not, even at some of today’s lesser levels. It’s completely speculative at this stage with very few use cases, and limited utility. There are a lot of use cases out there for tokens and blockchain technology, but unfortunately the landscape is early and they have yet to emerge or be scalable. The current value is mostly driven by demand (emotion).
    • Where do you see the value in crypto? I see it in the ability to fund projects and solve use cases that typically have major regulatory, cross-border, transparency and fidelity issues. For the tokens themselves, some stabilization has to occur before they could be considered a bankable tender or store of value.
    • Do you think Bitcoin is here to stay? No. I think Bitcoin and a chunk of this first wave are going to be the Webvans and eToys of this phase of the internet. They will garner attention, bring crypto into the public awareness (as they have done), generate the bubble we’re seeing and eventually crash and go away. The very early adopters and insiders will have made money and sadly the middle- to late-moving general public is going to take a bath on this for the most part. We have seen a chunk of this already, starting in late December 2017. Of course this didn’t affect your cousin’s friend, who everyone knows paid for his house and wedding by day trading crypto for the last 12 months. Does anyone remember 1997-2000 in tech? Yeah, it’s probably gonna be some of that again.
    • What will happen after that? The current influx of capital into the crypto landscape will continue to accelerate awareness, infrastructure growth, adoption and hopefully the maturation of real utility in the token economy. This should be coupled with applications of crypto signature, blockchain or tokens which create value that benefits not only investors, but hopefully humankind. The biggest and most transformative companies in this space are probably still living on the back of a napkin or in a dorm room somewhere, waiting to emerge.
    • What are you actively doing with crypto right now? In short, I’m just watching, learning and digesting, curious to see more applications evolve. I’m also trying to be very selective and pragmatic about placing any additional bets. Like many, fighting the urge to speculate.

      More specifically:

      • I’m sitting on my coinbase account from the cigars, seeing if it gets stupid again in 2018 or I cash out at some point on the ride down. Major haircut in last 3 months. Easy come, easy go…
      • I’m curious to see how my Polychain hedge fund and venture fund bets perform and what I can learn from following their approach from a pure economic sense. I don’t consider it an alternative investment like other traditional hedge funds. I look at it as an early-stage direct investment and accept an appropriate earlier stage risk profile (i.e. I’m aware it could go to zero).
      • I’m rooting for the next wave of above board crypto entrepreneurs and their ability to be transformative in their spaces. I have some close friends applying crypto technology to digital advertising at a company called Amino Payments in Philadelphia. I’m happy to support them with time, capital or connectivity where I can. It’s also fun to live vicariously through them here and there. #goteamcyan
      • I did calculate the risk profile of giving my wife a special Crypto Kitty for our 10th wedding anniversary last month, but chickened out.  I need to monetize or offload these damn things. What better utility than more gifting! I’ll probably keep Captain Lou, though. An homage to pro wrestling’s golden era…

    Overall crypto is has been fun to watch, fun to learn, fun to speculate and certainly fun to imagine the possibilities of the medium to long term. Tokens are the protocol layer. The mature applications have yet to show up. Imagine if you could have invested in TCP/IP (internet protocol) in the mid 90s? Way early. Amazing upside…. But I would caution that anyone should expect that speculative or early bets will also have the requisite and associated risks.

    So remember kids, the Bitcoin in the red dress may leave the party with you, but I promise it’s not going to marry you. We’ve seen this play out before in the 2000 tech bubble and again in the 2008 real estate collapse. The damn internets are certainly condensing the hype/fund/bust cycles, so place your bets wisely and don’t get caught up – or do dip an toe in, and get ready to #HODL along with everyone else.

    …and yes I know Warren Buffet doesn’t like crypto investments, but he didn’t like investing in the internet for a long time as well.

  • How to Get the Most From Your Executive Coach

    Recently, I posted a podcast with my third executive coach from my RevZilla tenure. During one of the parts of our discussion (which will end up being 3 podcasts), he asked about my experience utilizing executive coaching as a whole.

    I dove deep into the weeds on how I thought about external coaches and the tremendous value I gained over the course of my three coaching relationships beginning in 2013.

    I also noted that executive coaches, or “grey hair that can’t fire you”, became a tremendous asset not just for me but also for some other execs on our team.

    After that conversation, I wanted to formally crystalize my thoughts on finding and getting the most out of the external executive coaching relationship.  I am asked about this topic a fair amount and have a bulleted email that became the basis for this post. I hope any leader, regardless of their stage in the start-up to grown-up lifecycle, will find value in my experiences.

    The Relationship

    I’ve always been amazed at how quickly a person, including myself, can level up their thinking with access to an experienced ear who’s trusted enough to hear the darkest secrets or biggest concerns. Most times those things are just not meant to be shared with spouses, board members, co-founders or friends. Those people have a vested interest in your company or personal success and they will end up being affected by the stress you are sharing or worse feeling the need to somehow act on the new information.

    It’s also important to note that working with a coach is a different dynamic than informal advisory or mentoring relationships. I have been lucky to have many experienced friends and mentors in my life who offered me invaluable time, advice and friendship over the years. I could always rely on them to be there for me. They still are, as I am for them. But while I certainly consider my friends part of my personal advisory board of life, I would never want to risk a friendship by implementing a somewhat rigid and transactional structure around our interactions. Why risk removing the joy from the relationship? It’s the same reason I would not want to bring a close friend into a formal board role as a fiduciary and vice versa. Those relationships are not meant to be transactional.

    My decision to find and formalize an executive coaching relationship arose from the following needs as I attempted to scale the business and myself as a first-timer.

    I wanted to pay someone to:

    • Professionally focus on me via a defined scope of time and responsiveness
    • Be part of my regular weekly cadence (usually 1-hour call or Skype) as well as on-call via phone or email
    • Take a deep dive on my materials and company when needed
    • Come meet with my team in person or via Skype if needed
    • Actively listen to the worst of it and help me problem-solve or find clarity
    • Always give me their unvarnished opinion, even when it hurt
    • Receive assigned to-dos from me
    • Be accountable to me for delivering their agreed-upon scope of work

    If you were questioning before why I did not want to have one of my friends in this role, I hope it’s become more clear. You undoubtedly bond with people who care enough to offer tough love, but there is always a high risk that once the nature of the relationship changes to work, you can’t go back. Again, it’s the same risk as hiring friends or family in other instances.

    Inputs and Outputs

    Amalgamated over my experiences with the three coaches, here is what I learned about what a great coach offers and should feel like:

    • Has direct personal experience in things you want to learn (technical, leadership, management, etc.)
    • Earns your trust quickly
    • Is a excellent and active listener
    • Asks great questions and mines for root causes
    • Listens dramatically more than talks
    • Plays a great devil’s advocate
    • Encourages you to do things, but does not demand things or create more work for you
    • Forces you to crystalize your thinking
    • Enjoys talking to you
    • Should be selective in who they work with and really qualify you as much as you qualify them
    • Genuinely cares about you, your life and work
    • Feels like someone you’d probably still keep in touch with even when your formal (paid) relationship is over
    • Are well connected and will connect you with other like-minded leaders they know
    • Will inevitably run out of playbook, stories, experience to share

    The last bullet is notable because in each instance it led me to scale back my communication frequency from weekly to ad hoc with the individual. I found myself leaning out when I felt like the regular time I had scheduled could be better spent on other productive tasks or avenues for learning. In hindsight, this was my indicator to look for the next coach and playbook that I wanted to bolt onto my skillset and add to my support structure.

    My Coaches

    My first coach and I connected in 2013 when I was trying to figure out what it meant to be CEO of a company in fast growth mode. I continued to utilize coaches through the end of my operational tenure with some breaks in between. Here is the rundown:

    Coach 1 – 18-month duration – I tapped him for CEO coaching, CEO playbook evolution and absorbed it voraciously as he had decades of chief exec experience. He was super-smart and had seen a ton of life. He was not local and we have only met in person once or twice. He also helped my co-founders and I negotiate with a potential strategic acquirer that we ended up turning down 2013 (and again in 2015). I was a first-time CEO and wanted to learn by “renting his experience” (His words. He had so many great one liners).

    We don’t talk that much now, post working together, but I still have a strong respect for what he brought to the table. I found him by reaching out to him via his blog after reading him and following him for some time. I first became aware of him regularly participating in the comments section of a VC blog I follow. As a former successful multi-time CEO, he is coaching for the joy of sharing and in my opinion, living vicariously through current operators (which we all do post ops). Coaching was not his full time focus. He was not expensive for what I received. Considering the business was paying him, it was basically free compared to nearly any other investment which was adding any real or immediate value for my senior team. We sunset our formal cadence when I felt I needed to address other parts of my playbook, mainly marketing.

    Coach 2 – 14-month duration – I found him primarily for a CMO coach/ exec coach as I was feeling better about my evolving framework and approach to CEO. I wanted a seasoned Marketing Exec to help with team, process, strategy. I also wanted someone to help me understand all I didn’t know about brand, marketing and customers. I am a self-taught marketer and I wanted fundamentals and more expansive brand / marketing thought to build taller and faster on an already solid brand foundation. I also wanted another experienced confidant to talk me off the ledge here and there. I pinged my network and was introduced to him by an acquaintance who had worked with him at one time.

    He is an amazing human, former CMO, and new to coaching as he had recently left a CMO gig and had some time to kill. We originally spoke informally via Skype and he knew I was looking for help, but he was non-committal post intro from our mutual friend. We both clicked and after a few Skypes he offered to spend time with me weekly, not knowing when he would be going back to a full-time role. Our formal coaching and weekly calls ended when he took his first CEO role. We had become good friends and I ultimately brought him on our collective company board post Comoto deal. He helped us tremendously and spent time with others on my team. His cost structure was dictated by him and was real for him as an individual but insignificant in comparison to other people related company costs.

    Coach 3 – 18-month duration – He was a CEO / exec coach for me pre and post RevZilla / Cyclegear / Comoto rollup in 2016. Certainly a great exec coach, but our relationship was less operationally focused than coach 1 or 2. He was a more sounding board, devils advocate and shrink. A chief executive debugger if you will. He helped me most during my difficult decision-making process to leave day-to-day operations in 2017. I sourced him through my network of operators and VCs via an email denoting I was looking for a new backstop.

    He found me in “war time” when the things I needed were more specialized, relating to M&A, deal and private equity dynamics. I had leveled up a ton from “CEO 101” I’d done with my first coach years earlier, but I do believe Coach 3 would have been an excellent resource if I’d still needed that playbook. He was a great listener and sounding board. He is a former CFO and professional CEO coaching is his primary business. It was a higher cost investment for the company relative to my other two coaches, but he only had a few clients and the stakes for the seat I sat in were even higher at the point we connected. Still a relatively low investment for the company compared to other salary and related expenses. Our formal relationship ended when I moved on from operations.

    Putting It All Together

    In sourcing my coaches, I used my network, shamelessly contacted people who I thought I could learn from via wherever I could find them and set a low level of formal expectation initially to try to open a dialog and draw them in. Be scrappy, be up front, show commitment and be humble. You’d be surprised how many people out there may be open to helping. Remember, in most cases, helping someone else solve a real problem makes both people feel great.

    Since 2013, I have found it invaluable to have regular access to a person who had no vested interest other than seeing me happy and helping me improve – no strings attached. That is a powerful thing. These people played an important part in my success, as well as the success of the company.

    Reflecting on all of it, my keys to success of the coaching relationship are as follows:

    • Their experience has to be credible, deep and relevant to your stage of personal and company development
    • The interactions need to be regular enough (weekly?) so that they really know you and know what’s going on at your company
    • You need to be able to trust them
    • It’s about improving your decision making, not about them making decisions for you
    • You need to remove your ego so you can tell them what is really keeping you up at night, sometimes embarrassing yourself in the process. It’s uncomfortable. Get over it.
    • You have to really want to improve yourself; don’t waste your time or money if you think you are done learning

    Also, don’t hesitate to help your people find their own support outside the office and pay for it if you can afford to. If they can get better without increasing your managerial time overhead, that is an obvious win. What are the extra hours of your time coaching them worth, compared to paying their coach’s monthly rate? To be clear I’m not recommending you fully offload your managerial duty, just augment it.

    I would encourage any founder, CEO or executive to “find some grey hair who can’t fire you” (another magical coach 1 ‘ism), commit to the process and marvel in your ability to accelerate your efficacy and sleep better at night.

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