Anthony Bucci

I’m a founder, CEO, brand builder, investor, tech geek, family man and juggernaut. I’m most known for RevZilla. Expect a bit of storytelling, inspiration and insight as my different roles and perspective continue to evolve. I won’t settle and neither should you.

  • Day-to-day productivity, people management, scaling teams and planning cycles are a huge part of a company’s journey from start up to grown up. They are also foundational within a person’s journey from green to experienced.

    One of the biggest challenges is for someone stay ahead of the company growth and complexity curve while continuing to optimize the outputs and outcomes of their purview? This applies to founders, CEOs, execs and all employees on some level in a growth environment.

    I always found this a satisfying and formidable challenge to tackle and it remains a frequent topic of conversation in my circles at all levels.

    Over the years I have compiled a suite of books, articles and personal anecdotes that serve as quick references on some of these topics. They can usually quickly level up someone’s thinking and tools, or at least highlight the breadth and logical outcomes of their potential decisions.

    If you don’t have your own list of useful links, I’d encourage anyone to start curating and collecting. Very easy to organize by topic. Invest the time now for the payoff of usefulness later.

    This week I saw one of the most useful articles in a long time on Hacker News from a CEO Coach / Operating Partner / VC named Matt Mochary. It was an downloadable e-Book centered on scaling yourself and your company for founders, but much of it could be very useful to all levels of staff.

    I have not made it through the entire e-book, but I have dug what I have seen so far. I’m thinking about adding my own commentary to the sidebar, where useful, and sharing it broadly with my network.

    Even after a quick pass, it’s clear Matt has 1) seen or lived a ton of companies from startup-to-grownup and 2) taken the time to organize and concisely record a playbook of tools, frameworks and things to think about.

    Regardless of your role or your company’s stage of life, there is a lot that many will find useful in here to level up their efficacy and impact.

    We all produce the best results when we tailor and refine our playbook to our situation, prefered style and tendencies. But when you are doing it for the first time, sometimes a cut-n-paste baseline is better than nothing and much of the cut-n-paste-ables from Matt, happen to be pretty good.

    I’m going to print this, bind it and stick it on the shelf right next to Dalio, Horowitz, Theil, Wickman and my other faves.

  • These days I meet with a ton of founders and execs who are trying to scale themselves and their contributions ahead of the increasing slope of their businesses’ growth. Personal productivity comes up often and it always resonates with me, as well.

    I’m sure I didn’t invent the following, it’s just my implementation and nomenclature of a time and productivity framework that became hugely impactful on my ability to get the right things done.

    It’s worth noting, that this type of approach will also benefit contributors at any level, not just senior people, managers or exec’s.

    I could have trimmed out some of the personal texture to save length, but my hope is that some of the nuance stays intact to highlight added positive and potentially negative ripple effects.

    Over the course of RevZilla, I became a productivity nerd, constantly testing, learning and optimizing my day, week and time along the way. In many cases I also had my Chief of Staff, Lee Anne, to help me refine and implement new strategies.

    The goal was to get the most out of the schedule while wasting as little time and effort as possible. Unfortunately, I didn’t realize that until I reached a point a few years in where I literally could not extend my day any earlier or later. Working smarter and prioritizing effectively became key.

    Also, being more productive is not just completing an array of more tasks during an efficient time window, but also ensuring that progress is made on the most important things.

    I could write a novel about my thoughts on the topic and completely detail my daily routine, but for this post I want to stay focused on what I think was the cornerstone of my productivity in its most evolved form: The High Velocity Focus Block.

    High Velocity / Low Velocity Work

    I used to use the terms High Velocity and Low Velocity to talk about the value of tasks. I stole this terminology from a blog that I read at some point that I could not find to link here. I also think this is probably stolen on some level from Agile metrics. Regardless, I thought of this nomenclature in the following ways:

    High Velocity work moves the business forward. It usually solves multiple problems at once or creates meaningful opportunity. It is the work that you, and only you, can and should do. For leadership and managers, this is what should be left after everything has been delegated appropriately. This most important work is also usually the hardest work that takes the most focused time and energy. This work is fully engaged high level problem solving, invention, strategy and planning. Many times, this work is the heaviest lift, as you are solving or creating things for the first time. If you are prioritizing well, this work is high leverage.

    High velocity work is the work that you and the business can’t afford not to get done.

    Unfortunately, Low Velocity work exists, as well. It is the mortal enemy of the completion of high velocity work – and it’s everywhere and constantly attacking you.

    Your office environment is probably a sea of urgent-unimportant interruptions or lesser tasks like email that are easy to complete and satisfy your lizard brain’s need to check the box. You know they don’t really move anything forward significantly but they are all around you and at times can trick you into feeling productive. Other culprits include group meetings with no outcome, quick discussions, random people dropping in, lunch or coffee meetings and other things that are not worth your time but feel good. They can easily siphon whole days (weeks?) away if you let them. Once RevZilla hit the 10-15 FTE mark and beyond, it increasingly felt this way for me until I did something about it.

    I watched myself, cofounders and colleagues struggle with the same frayed edge and frustration. Many times, there was a feeling of working all day on other people’s stuff (operations) only to stay late or click back on when everyone left to get to the things that were actually needed. For me, in many cases it was also sporadically coming in early to “catch up” while routinely giving up my weekends to push the business forward.

    High Velocity Focus Block / DND

    My eventual solve for the misprioritization of productivity was the High Velocity Focus Block, or what my Chief of Staff Lee Anne and I called Do No Disturb, marked off as “DND” on the calendar.

    Every day from 6am to 9:30am I prioritized a 3+ hour block of uninterrupted time when I was the freshest to work on the most important, hardest and valuable elements of my universe.

    I found it so valuable, in fact, I would get up at 4:45am daily to be in by 6, just to maximize my allotment of unadulterated time. This from a guy who scheduled all college classes MWF so I could sleep until 2:30pm on Tuesday and Thursday.

    It literally changed my work life, productivity level and it had a major effect on my focus and demeanor just by way of lessening the constant anxiety of feeling like I was always trying to rush through daily things to get back to the most important stuff. I now knew when the next guaranteed block of time for my focus work was. I could be more focused with everyone else because I had put myself and the business first and then scheduled everything else around it.

    I found that I would get so much done in my Focus Block that it didn’t bug me if after my first meeting started at 9:30am the rest of my day was filled with supporting other people’s agendas, internal and external meetings, smaller less important or urgent tasks, email and other low velocity box checking. I viewed it as a bonus if I got back to the big stuff at all.

    I did my best to schedule the rest of my day on a descending scale of things I participated in versus drove myself and tasks that were less important or less difficult to complete. We all get mentally and physically tired. Why put myself in a position where something that needed “A effort” would require a second wind that I may or may not actually have at that moment in that day? If I was driving it, I usually would schedule it right after my DND, typically before lunch, and if it was going to be a multi-hour affair I would sometimes infringe on my Focus Block, to guarantee that my team and I were all fresh and focused.

    It’s worth noting that my ideal goal as the CEO of a properly scaled org was to delegate all ops and get to come to work and decide where to apply myself, focus or tap in. In nine years that never happened.

    We were always growing too fast, things were always changing too much, I was also the defacto CMO until my transition out and there was always at least one or two other exec seats open. All that created a need for regular cycles and contribution to the day-to-day on my part. My daily regimen was my weapon against my actual reality versus my idealistic goal.

    It’s also worth noting that you can make the “well I’m a night owl” argument. I was, too, early on. I started as a late-night guy earlier in my career and into RevZilla’s first few years. I gradually started my day earlier as time went on. While I do think early is a easy choice for many, my argument here is not for early, it’s just for active prioritization of a person’s freshest time blocks.

    The High Velocity Focus Block can be at any point in someone’s day and people’s rhythms can be different. The goal is the regimentation and anchoring of the time block to allow you to prioritize and make progress on the right things and let the rest of the day take the impact of having to hit the moving targets.

    Take into account what the cultural norms of the org, your team and the other execs are when choosing your regular time slot. Your changes will impact them and potentially set an example.  Also, if you are not the CEO, your ability to stave off interruptions from your manager and have them hopefully leave you alone needs to be a consideration. Hard to ignore a knock-knock from the big boss at your door if your time happens to coincide with their desired window to pop-in.

    Implementing a High Velocity Focus Block

    Whether you are a founder, CEO, executive manager or even individual contributor, there are simple elements to this framework which can really bring a ton of value. Here are some basic steps for how one might go about utilizing this in their own daily routine:

    1. Make / Find the Time – Commit to finding or creating at least a 2-hour (preferably 3-hour) block that you will place at some point in every day that will not change. You may have to adjust your schedule (it’s worth it). You need at least 2 hours because many of the hardest and most important problems need 30-60 minutes just to allow you to fully immerse and catch your brain back up with all the relevant details of where you left off. I called this “booting up.” Many times you are just hitting that magical “flow” state at the hour mark, and when you get there and realize you only have 1 hour left after you’ve fully spun up, it will leave you wanting more.
    2. Pick a Regular Time Slot – You goal is to find your peak mental, emotional and physical energy to maximize productivity. Think about when you are freshest and most excited about solving the hardest stuff. (“Finding your peak” comes from a great productivity article I read years ago here.) Many Coders talk about late nights, many managers, execs or people with families I know use the early morning, but it can be really any time of the day. You just need to know that you can stick to it, schedule around it daily and that other people (boss, team, peers, clients, etc.) will respect your desire to disappear or at least do their best to leave you alone.
    3. Schedule, Commit, Communicate – Place your focus block on your calendar daily and commit to scheduling around it. Communicate to others what you are doing and why, if they ask or need to know. If you are not using the calendar with stringency and fidelity at this point, I encourage you to begin taking it seriously and respect it, as it can be a cornerstone of defining where your time goes. If you don’t, others won’t, either. Depending on your place in the org, an AA or EA is huge for helping with this. Scheduling is such a time suck overall. More on offloading low velocity and scheduling at a later date.
    4. Your Manager – If adding the Focus Block to your day is going to interfere with time that you are usually casually reachable by your boss, make sure you at least inform them of what you are doing. I’d potentially frame it as “trying something new to boost productivity”  and ask for a blessing. Give yourself some breathing room and see if you can get some buy in, versus painting it as you are fully committed to this exact approach out of the gates. You may find your self tweaking it as you go. Positioning as “Trying” it sets the stage for adjustment downstream. Much of this goes for your peers, as well.
    5. Your Reports – I always say great management and leadership is just like great parenting. It’s not about “do what I say, not what I do,” it’s about modeling what you want to see from them. Part of coaching people up is giving them a role model, exemplar or playbook to aspire to. The best way to get them to raise the bar is to demonstrate how you’ve raised your own. Being disciplined about a regimen that puts the hardest, most valuable stuff at the center will speak volumes about what you deem important and what you value. If your team’s normal schedule will be affected, start with a “I’m trying something new so this is why our team’s schedule is changing.” Don’t be afraid to communicate, share or even evangelize what’s working in the hopes they will adopt a path toward more efficient productivity that no doubt aligns with all of your and the company’s interests.

    Using The High Velocity Focus Block

    Post implementation, here are my rules for getting the most out of the 2-3-hour daily focus block.

    1. Become Unreachable and Invisible – Make yourself invisible and shut out the world. Shut your email. DND your phones. Kill messenger. Put your headphones on. Close your blinds / door / etc. Tell your assistant, secretary or EA, if you have one, to gatekeep like a champion while making a list of needs from those who attempted to drop by. Be sure to have your EA also ask for a sense of time urgency for each item / issue. You don’t exist unless something is literally on fire (which you can define). Train people this is the case. Explain why, if they ask. There is a huge cost to interruptions breaking flow. There is an even larger cost to actually context switching to quickly speak with someone, pick up a call or come out of the weeds on your current focus. To immerse again you will need some sort of mini “boot up.”
    2. Warm Up Task – Low Velocity of any kind in this block is the enemy, but I always found a 5-minute “warm up task” like answering an email or hitting something tiny, easy and quick makes it much easier to get momentum for tackling something larger and gets your synapses firing. Since I used a single TODO list, which housed low and high velocity followups, it was quick and easy to pick one thing. Be sure the warm up task doesn’t turn into 3 or else you just ate 15 precious minutes you could find later. This is the “Make your bed” principle from the General McRaven UT Commencement Speech in action. Some people don’t need this step. Skip it if you can.
    3. The List – Everyone has their own system, but somewhere, easily accessible and with good hygiene, have the list of the most important High Velocity items with quick links to where to find the work. I used Workflowy and many times linked to Google Docs. Your brain is for processing, not for storage. Write down at least the most important stuff concisely and cleanly and keep it prioritized. Don’t waste time deciding what to do. Look at your list, reorder quickly if absolutely needed and dive in. Reordering things is low velocity. Try to do this step late in the day before for both high and low velocity list items. Usually, 5 minutes is enough to tweak a clean list.
    4. High Velocity Work – The core of this entire structure. Use as much of this time as humanly possible to work on the most important and heaviest lift(s). Many times it will only be one thing. Outside of the warm up – no Low Velocity allowed. I found myself minimizing distractions and fully immersing, not coming up for air. I know others who baked in a coffee or bathroom break at the 45- or 60-minute mark. I was always concerned that if I prairie dogged up, those who needed answers from me would pounce, causing me to context switch and challenge my state of “flow.”
    5. Bookend – Take the last 15 minutes to come up for air and leave yourself a clean edge to come back to, at worst case, the next day. Put notes in the header, leave yourself gDoc comments, make a mini todo list at the top, update your main TODO list. Anything you can do to make it easy and immediate to pick up where you left off reduces the “boot up” period for the next block.
    6. Optional – EA Daily Rundown – Side note if you have an EA or AA, I found a ton of value in doing a daily 15-minute run down with my Chief of Staff / EA Lee Anne before my post focus block schedule started. I used the last 15 minutes of my focus block and started my “bookend” phase at the 3 hour mark vs 3:15 mark. I would bring her up to speed on progress I made and what I needed and she would help ident’ notables on the upcoming schedule and anything low velocity but notable that came in while I was heads down. For that to work, your support team obviously needs to come to start prepping while you are sequestered.

    Ripple Effects

    It’s worth noting that many people use any extra morning time upon arrival to check email, catch up on low velocity back log and “prep” for their day. I used to be in the same boat. My hack for this became email catch up block in the afternoon and before I left for the day. I also did 10-20 mins in the early, early morning after I woke up and before I got into the office. I also would batch some email and low velocity catch up on the weekend when I was home and it was harder to be fully focused.

    If you leave the low velocity unattended for too long, you will become a bottle neck and other people will start burning until they are important enough to move up your list. The “let it burn until it matters” method is laden with the managerial debt of eroding morale and toasted social capital. Avoid the negative ripple effect of becoming a uber-productive black hole that does not respond to others regularly.

    I did eventually evolve into working with a full time EA to take on all scheduling and to help filter and prioritize all velocities of tasks. It was super high leverage but that is a whole other post for another time. My point is that whatever your Focus Block is displacing in your current routine will have to be rerouted into less pristine time or potentially delegated, if you are able. Be aware of it. Plan for it. Again, no black holes.

    As a final side note, as I was putting this together, I was made aware of a productivity book called Essentialism which highlights an approach called “Top Goal,” I believe. I have not read it, but apparently the book is solid, covers a lot more than just this aspect, but the framework very similar.

    This is not surprising at all. Lots of talented people fighting the same daily battle are going to arrive at very similar solutions that are mostly just named or ordered differently. Mine was the High Velocity Focus Block, coded as DND on my calendar.

    So while there is some nuance to implementing, the framework is actually pretty simple when you look at it through the lens of “make sure you actually work on the most important stuff every day”. The hardest part, however, is committing to the time and then actually having the discipline to use it for truly High Velocity. Like anything else, it’s all about how well you can execute. I was never perfect at it, but I strove to be as consistent as I could be.

    All in, making daily progress on that which is most important will absolutely create a sense of foundational satisfaction for your day. You also will move the business forward, potentially reduce your weekend or off-hour catch ups, lessen your stress and model a killer example for those around you.

    There is really no downside. Argue with me.

  • Summer Reading List

    My kids are on summer break and I’m traveling a ton. Continuing to write has been impacted for last sixty days, no doubt. But in the absence of regular writing I have been offsetting it by reading. A lot.

    For whatever reason, rarely do I read fiction, if ever. I typically read for the purpose of learning something new. I find this especially true with biographies. People patterns show up again and again and I’m always trying to stand on the shoulders of any relevant experience I can find.

    I’ve also found that for the first time in my life, I’m in more than one book concurrently. A far cry from even 10-15 years ago, where other than short form internet or magazine, I would say I didn’t read books at all. What a missed opportunity.

    Here’s what’s on my recent list:

    • Give and Take by Adam Grant – In progress. Speaking to the nature of people who “Give, Take and Match” in all of their relationships. Seems like it’s headed for the thesis that “nice guys (givers) finish first” so long as they are not in a toxic “taker” environment. Originals by Adam Grant was great. Digging this one so far, but a slower read than I was expecting. I think Brock gave me this. Thanks Brock!
    • Poorly Made in China by Paul Midler – In progress. Fascinating behind-the-scenes look at what it’s actually like to manufacture in China. It spans the manufacturing rise in the 20th century to now and how the norm is potentially changing with China’s change in global stature. Interesting view into collective Chinese culture as a whole. On my list for a while. Finally getting to it.
    • A Higher Loyalty: Truth Lies and Leadership by James Comey – Recently finished. After the reality show car wreck which was Fire and Fury, I wanted to see the perspective from the other side. Broader and more interesting than I was expecting, following Comey’s full career in the public and private sectors. Everything from working for Giuliani to the prosecuting the mob. Obviously speaks in detail about the Clinton emails and his dance with The Donald. Quick read. And if you’re wondering where I fall, I think the current administration is a joke and hurting this country. A vote in that direction is completely indefensible at this point….
    • Tiger Woods by Jeff Benedict – Recently finished – Oh for Christ’s sake, if 25% of this book is accurate… Testament to the fact that kids are not born screwed up or jerks, their parents do it to them. This story is as interesting as it is sad. The greatest golfer who ever lived never had a shot at normal or even reasonable from the time he was a toddler, and there was nothing he could do about it. I had never read any of the other Tiger books, but apparently this has a fair amount of retelling from other sources. Quick read.
    • Hillbilly Elegy by J.D. Vance – Recently finished. Follows the arc of a family and their community from rural Kentucky Appalachia roots to a migration Ohio’s rust belt in search of upward mobility, only to be met with the eventual rust belt manufacturing decline and its impact and reinforcement of the poverty cycle. Very sobering societal commentary through the eyes of a man who grew up there and eventually escaped the odds. Quick read.

    Branson and McCain books up next, along with Factfulness, Thinking Fast and Slow and the The Innovators by Isaacson.

    Side note, I still buy actual books. I find that I enjoy it less and retain less when I’m not actually flipping the pages with my feet up. I have hoarder tendencies, yes, but I when I look at the book up on the shelf in my office I can recount my takeaways from it pretty well. I do this often. Out of sight, out of mind for the e-books, I guess.

    Also none of these are affiliate links :-p

    #leadersarereaders #neversettle

  • 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.

    #thiswasonlyamatteroftime

  • 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, Overstock.com 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.

  • 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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