Bobby Henebry

Chief Investment Officer at Elway Capital

Bobby Henebry, CFA is a passionate entrepreneur, leadership facilitator, and helper of people across cultures. He serves as President and Chief Investment Officer at Elway Capital, LLC, an investment firm based in Denver, CO. He is a globally recognized speaker, having presented to audiences in 20 countries on understanding blockchain and digital assets, which builds on his extensive experience in traditional investment advisory roles.

He previously served as a partner at DM Capital, an investment fund with a concentrated portfolio of listed equities. Bobby also spent 11 years at SeaBridge Investment Advisors as a partner, advising wealthy individuals and family offices on global allocations across asset classes.

Bobby earned a BSME (’03) and MBA (’06), both from Georgia Tech. He is a member of the Society of International Business Fellows (SIBF), and is very active in the Middle East Leadership Academy (MELA) and Central Eurasian Leadership Alliance (CELA). Bobby has mentored entrepreneurs in the Global Good Fund (GGF), Girl Power Talk, Georgia Tech Startup Exchange, and other communities. He has also served on numerous non-profit boards including SIBF, MELA, Urban Recipe, and the John Dau Foundation. Bobby has traveled to 55 countries. He loves music, and in 2017 founded the YouTube channel Chord Savvy, a music education platform.

What is your typical day, and how do you make it productive?

I have three types of days: office days, travel days, and leisure days. Office days usually are 8-12 hours starting with me typically at the office by 7:00 AM, and are filled with Zoom and telephone calls, emails, and getting different kinds of project work done (reviewing investments, organizing financials, operational tasks, etc.). While travel days are what I most enjoy because I get to connect more meaningfully with people and ideas, attend conferences, explore other cultures, expand my network, find opportunities, and occasionally speak to groups. In many cases, I also get to re-engage with people whom I already know, which helps me compound relationships and trust further. Starting early, staying engaged with a “get stuff done” attitude, and working late help me get the most out of both office and travel days. Leisure days come in various forms but generally involve sleeping in, meals with family and friends, playing music, catching up on the personal projects I have not made time for, and recharging to be able to get back to my busy-schedule days.

How do you bring ideas to life?

To bring an idea to life, you just have to do it. Don’t struggle with perfection, don’t get hung up by your ego, and don’t take it personally if it fails. Technically, leaving an idea inside of you is a form of failure because the idea doesn’t exist outside of the world. Share an idea or draft deliverable with three people, and if they say bad things about it that’s fine. If they say wonderful things about it, that’s also fine. In any case, test each idea in a market of other opinions. And as you test more ideas, you get more information, and you can then make a decision on which idea you want to pursue further. Testing ideas with other people brings them to life while providing more insights for you to make better-informed decisions. Ideas thrive outside the world, so don’t keep them captive inside your head.

What’s one trend that excites you?

One trend that excites me is blockchain and crypto. I’ve been in this space since 2016 when I started mining ETH at home, and I continue to have a strong interest in much (but not all) of the ecosystem. I know that it’s not for everyone, but I think it’s a fascinating area at the convergence of some of the most talented people with huge financial resources to use these newly available tools to solve very interesting problems. There is a lot of hype in the space too, so distilling it down to what I think is realistic and practical is part of the challenge and opportunity, at least in my opinion.

What is one habit that helps you be productive?

When I meet someone new, I connect with them on LinkedIn and I send them a short note that says something like ‘hey, great to meet you at the XYZ conference’ or ‘hey, I really enjoyed our meal together’ or ‘I’m so glad that X introduced me to you.’ The reason I document that info is that five years from now, I may come across that person again, and I want there to be a record of why and how we originally connected. That habit helps me advance the relationships further, and/or check with our common connection for additional insights on the person and what they are building.

What advice would you give your younger self?

The advice I would give the younger version of me is ‘Don’t let perfection get in the way of good enough.’ That’s why whenever I’m on the go and I come up with a business concept, song idea, or article outline in my head, I try to write it down in bullet points or record myself on my phone as soon as possible, even if it is disorganized. I just want to capture the essence of the idea, and then share a paragraph or one-pager with someone who can give me feedback as soon as possible. I used to not track or share ideas because of the perfection trap. I kept them safely in my mind where no one could critique or pick them apart until I spent a LOT of time making them perfect (or so I thought). I just figured I would get around to developing each idea later, and I either forgot the idea or got busy with other things… For example, my YouTube channel Chord Savvy sat on a piece of paper for a few years before I finally just built the thing! And I lost lots of opportunity for growth while I waited… My “perfect” behavior limited the possibilities for collaboration, new insights, and simply bringing ideas to life.

Tell us something you believe almost nobody agrees with you.

I’ll clarify with an example: Let’s say you’re driving a car, and you’re in the left-hand lane at a traffic light about to turn left. There are five cars behind you, and then somebody starts walking across the street when your traffic light turns green. The pedestrian is breaking the rules, and risks blocking a group of cars from turning. Most people, if in the first car, will wait and let that pedestrian cross because they believe that’s polite to the person walking (presumably in a hurry). Obviously, if the person is directly in front of your car, you can’t do anything. But many times, pedestrians in this scenario are just beginning to step off the curb a few lanes away from you, and the lead car waits a few seconds until the pedestrian is in front of them instead of asserting their right of way (and basically telling the pedestrian to walk back a step and wait their turn). In my opinion, why wait to be polite to one person who is not following the rules when you’re actually being rude to the five people behind you who have patiently followed the rules (even if they might also be in a hurry)?

Let’s extend that example to an organization. When I see one person out of alignment with norms and values of an organization, especially when in a leadership position, and I hear other people grumbling and “honking their horns” about it, I will begin advocating for the group. But there is a strange human tendency to ignore the group and focus on the needs of an individual. We support what is in front of us, and ignore what is behind us or hidden from direct line of sight. In an extreme case, this is how authoritarian structures are formed. Consistent, selfish behavior by a strong personality that ignores group norms combined with an unwillingness by the group to come together and make the uncomfortable response (even if “right”). We often focus on one person or leader instead of the group. Excuses are made to justify them, and groups are afraid to call out some individuals because no one wants to be the squeaky wheel. Stepping up is hard; change is hard. And groups tend to take the easy non-confrontational route instead of addressing issues head-on.

What is the one thing you repeatedly do and recommend everyone else do?

Have integrity about your commitments. If a meeting is supposed to start at nine, be there on time (preferably early). If a meeting is supposed to end at ten, leave at ten if you have other commitments. If you say you want to reconnect with someone over coffee or dinner, put it on your calendar immediately. Get into action in order to convert intention into formal commitments. If you are uncertain about specific timing, then put a placeholder reminder like “ping John today” on your calendar during a day you know you will have downtime to catch up, so you won’t forget the intention to connect with someone on some topic of interest. Always bring commitments down to reality by putting them on your calendar, and be accountable for the time you have allocated to others in order to get the most out of each day while honoring their time as well.

When you feel overwhelmed or unfocused, what do you do?

When I feel overwhelmed, I start working on a simple task I have resisted (cleaning my desk or car), and I then do more tasks one at a time to build momentum. Simply start something. Or I sometimes start with the hardest task at hand so when it’s done, it’s easier to move forward with everything else. Additionally, sometimes when I’m overwhelmed and can’t start, I know I need a break. So I shut everything off, chill outside on my patio, play my guitar, go on a walk, and/or watch a movie without being hard on myself. Sometimes you just need a little kindness from yourself.

When I feel unfocused, I often pull together a scattered collection of sticky notes, to-do lists, and a work diary with tasks I am yet to complete. I then go through them one-by-one and put things in order on a new sheet of paper or sticky note. It is a simple task that is a step towards decluttering the multitude of tasks in my mind, and it refocuses me on activities I want to engage. Other times, I simply clean up my house or my office to bring order to chaos, and that gets me back into a good energy space of getting things done! I can then build on that momentum and focus.

What is one strategy that has helped you grow your business or advance in your career?

I would say to be open to unexpected possibilities and put yourself in new and uncomfortable situations where you can find new ideas and people. But don’t always do it randomly. Think about your bigger picture or the structure of what you’re doing for your life and happiness. Attend events and go to spaces that are aligned with what you want to accomplish (even if you feel a bit scared). Eventually, new relationships and insights will move you toward the vision of what you want to accomplish, as new possibilities begin to unfold before you.

What is one failure in your career, how did you overcome it, and what lessons did you take away from it?

When I was 36, I was a partner at a wealth management firm that I’d been at for nearly 11 years. I was very frustrated at the time because of the lack of clarity on the future of the firm, and I didn’t feel like I could change the culture or get the firm to grow the way the broad team wanted. They were all great people in the firm! We just had different and uncoordinated views on what was next, and it took me time to realize that I needed to open up my eyes to broader possibilities. I had also simply outgrown the potential that the firm offered to me professionally, and it was time for me to embark upon a new adventure. So I did the uncomfortable thing, and I quit my job and spent a year-and-a-half traveling the world to 30+ countries. And through my travels, I discovered all sorts of possibilities and great entrepreneurial jobs that were a better fit for me.

I learned two lessons once I broke free from my old life. First, sometimes you’ve got to trust your gut, and if you can’t change your organization, then change yourself to find opportunities and happiness elsewhere. Secondly, I learned that I could walk away from a prestigious role and make way less money but way more happiness in life, and that is liberating information for the rest of my life!

What is one business idea you’re willing to give away to our readers?

I believe everyone has a business idea that they want to do but are afraid that other people might steal it. To that generally irrational fear, I say the value isn’t as much in the idea as it is in the execution. Sure patents and trademarks are valuable, but most ideas don’t work on their own and many businesses don’t need that kind of I.P. (intellectual property). They need constant drive, input from others, investment, attention, and connection to thrive. So the business idea I’m willing to share is to inspire YOU to let go of your business idea, share it, test it, prototype it, and let people challenge it. That’s how you make it come true.

What is one piece of software that helps you be productive? How do you use it?

Among all the latest software and technologies out there, my favorite remains spreadsheets. That’s because deep down I believe that it’s not the software that gets the work done, it’s actually me. And spreadsheets are one of the greatest tools to get things in order for me to remain efficient. I am a nerd at heart!

What is the best $100 you recently spent?

We have been expecting a baby, and Jessica loves massages. However, massages for pregnant women are difficult to line up and more expensive because of the medical risk. So, I gave her my credit card and said ‘put the massage on me.’ I don’t know how many she received, and it would probably cost way more than $100, but that’s a worthwhile investment in her health and happiness for our child.

Do you have a favorite book or podcast from which you’ve received much value?

The book that changed my life the most is “The Greatest Salesman in the World” by Og Mandino. It’s a short book with just over 100 pages of content, but it takes 300 days to read. That’s right! 300 days… The story is about an incredibly successful Arab merchant who shares his wisdom in the form of 10 short scrolls with his young protégé, who is eager to access the key to his mentor’s vast success. But the scrolls are about more than business. They are really fundamental principles on how to live a more engaged, fulfilling, and meaningful life ultimately. Each scroll contains wisdom that you are invited to read three times a day for 30 days. So, by doing these 900 readings over 300 days (10 scrolls * 30 days * 3 readings/day), the book prescribes an accountability guide to putting powerful ideas into action, thereby enabling the reader to reprogram their habits, and experience further success in life.

What’s a movie or series you recently enjoyed and why?

I recently watched Stranger Things, and I loved the series. Deep down I am a nerd and a passionate musician! I am also a HUGE Metallica fan, which is the main reason I finally decided to watch the show… My band played “Master of Puppets” at our most recent Halloween party, and our guitarist dressed up as Eddie Munson, which left me intrigued about the connection between a character from the show and a super-awesome song I have spent many years performing. So I began watching the series only to then wait impatiently for the song “Master Puppet” to be honored. Any time a Metallica lyric happened to overlap with dialogue from the show I got super excited. But I had to continue to be patient… Funny enough, the song “Master of Puppets” didn’t get played until the last episode of the last season (4) that aired, BUT it was well worth the wait! Looking back at the series, I loved the nerdy creativity, use of music from the period of the show, brilliant young actors, and how the series was filmed mostly in my home state of Georgia, which is a source of pride for all locals.

Key learnings:

  • Don’t let perfection get in the way of “good enough” because “good enough” lets you prototype faster into actionable ideas instead of staying stuck in theory!
  • Get out of your comfort zone and be open to unexpected possibilities and relationships that can totally change your mindset and life.
  • Trust your gut, and if you can’t change the organization, change yourself and your role.
  • Have integrity about your commitments that can accelerate you into new relationships and insights. Intentional action matters.
  • Advocating for the group is a more difficult leadership challenge than most realize, and how you advocate is often more important than what you advocate.