Bet on The Jockey and Not the Horse

When people ask me how I invest in startups, I share the most important part of my strategy: bet on the jockey, and not the horse.

I first heard this analogy about 5 years ago from Michael Loeb, an incredibly successful entrepreneur, who shared this advice while graciously hosting a weekend trip for myself and other entrepreneurs. Nearly every seed investor says something similar – that the team matters more than the product – but this analogy stuck with me for several reasons:

  • It captures how distinct the two entities can be, yet how powerful in the right combination.
  • It makes it obvious who is driving success. A great horse will go nowhere without a passionate, savvy and motivated jockey racing against the competition.

When I made the transition from angel investor to institutional VC as a partner at High Peaks, I reflected on my years as an angel and realized that any mistakes I made were because I had not fully internalized this advice. My new partner Brad Svrluga had a similar experience over the dozen years as a VC; as he puts it: “I’ve always understood the jockey-horse lesson, yet every single year I feel like I learn it again and understand more and more how true it is.” The lesson really screamed out at us both, when we recounted our wins and losses. Our biggest mistakes came from when we compromised this value or thought there were enough compelling reasons to ignore it; our greatest successes came from embracing it.

Taking this strategy to the extreme, Brad and I made some bets on jockeys before they even had horses. Our first example is Akshay Navle. When I was first introduced by an angel investor, I had no idea what to expect. I took the meeting out of courtesy and scheduled just 30 minutes – which turned into 2 hours. Akshay told me amazing stories about his work and life and experiences, from building the ecommerce site for B&H to the long winding road between his start up and Quidsi (the parent company of We got along well and I knew this guy was special – he had developed so many thriving and innovative businesses, yet he had a humility about him. He seemed like a young but talented jockey who expected his best race was still to come. We ended up working on a number of projects together, and last year, I brought him on at High Peaks as a Venture Partner.

Another favorite jockey is someone I met about a year ago when doing due diligence on a potential investment. I asked friends for contacts with experience in a specific industry, was introduced to Caleb Merkl, and was immediately blown away by how smart and insightful he is. We kept in touch and he later asked me for advice, since he wanted to be an entrepreneur but didn’t have a solid business idea yet. Like Akshay, Caleb seemed like a shooting star, so I convinced him to quit his job and become an Entrepreneur in Residence with us at High Peaks. That way he could learn from our approach and network, while developing his own business.

The plan worked well, and after about 6 months with us, Caleb teamed up with Akshay to develop a great idea and co-found a business together, with High Peaks as a seed investor. We may have lost an EIR and Venture Partner, but are more excited than ever because we get to be involved in this next journey. They are still in stealth, but we can’t wait to share more soon.

Brad and I love what we do because of this opportunity to work with great people.   We value great jockeys first and foremost (like Marc Lore of or Rahul Gandhi at MakeSpace), and this is the foundation for how we invest in people, not just companies, at High Peaks.

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High Peaks MBA Associates Program – Now accepting applicants!

High Peaks Venture Partners is an early stage venture capital firm based in New York City.  We are seeking current MBA students in New York to participate in our MBA Associates program.   The MBA Associates will be specifically working on two main initiatives. The first is the expansion of our Operating Partner Network and and Technical Advisor Network in which we connect our portfolio companies with potential operating and technical experts to leverage their expertise. The second is to work with our investment team in conducting industry research to help refine and inform one of the investment theses that guide our investment and portfolio support strategy.

In the expansion of our Operating Partner Network or our Technical Advisor Network:

  1. Identify leaders in the startup and tech community
  2. Discuss opportunities to join High Peaks’ Operating Partner Network
  3. Enter information in our CRM system
  4. Assist portfolio companies in learning best practices, getting market intel, and hiring via the use of our Operating Partner Network
  5. Networking is a huge part of what we do in Venture Capital and we think this is a great opportunity to start building a presence in the NYC tech scene

In the industry research project you will:

  1. Work with our investment team in identifying the appropriate topic and thesis
  2. Conduct interviews via our Operating Partner Network or Technical Advisor Network to gather data and insights
  3. Get intelligence and point of views from other others in the Venture Capital community
  4. Present your findings at the end of the program to the Partnership and all other participants in the program


  1. Strong business acumen. Ideal candidates are currently enrolled in a top tier MBA program. A strong interest in Ecommerce and SaaS really helps.   This is beyond knowing what SaaS stands for and/or having shopped on Amazon!
  2. You love networking and have a genuine interest in helping people, beyond just building a business. You need to be able to dig into people’s previous experience, motivations, and aspirations as well as develop an understanding of industry dynamics and can find the devil in the details.
  3. You work hard.  Hustle is your middle name.
  4. You are not an A—hole.  You might be a superstar genius but if people don’t always refer to you as a “really nice person” then you definitely don’t belong here.
  5. You figure sh*t out and can work independently.   We don’t need to hold your hand to figure out what you have to do next.

Timing and other details

  1. MBA Associate program is from Sept 2014 through early January 2015.
  2. MBA Associates will be working primarily out of the office as you are expected to mostly be networking and gathering data from the field.

Email me your resume or LinkedIn Profile link at:

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“We are all smart, Jeremy.”

CIA Director: What do you think of the girl? Jeremy: I think she's fucking smart. CIA Director: We're all smart, Jeremy.

CIA Director: What do you think of the girl?
Jeremy: I think she’s fucking smart.
CIA Director: We’re all smart, Jeremy.

It has been interesting to be on the other side of the table as the Venture Capitalist versus being an entrepreneur especially when it comes to evaluating the entrepreneur themselves.  I got a kick out of the fact that in our investment committee meetings that the most frequent response to the question “What do you think of the entrepreneur” would be “She/he is smart.”.  After seeing Zero Dark Thirty, I realized that it really is a crappy comment because it lacks any insights on the entrepreneur.  “We’re all f-cking smart” is now our immediate response when someone comments that the entrepreneur is smart.

So if everyone is smart, what else should we be looking for to determine if the entrepreneur will be successful?  As part of our evaluation process, we usually ask the following questions about the entrepreneur:

1. How much experience do they have that is relevant to the business?  Experience is a big deal.  Why?  Because you make less mistakes and mistakes equals cash burn.  Whether it is experience as a previous entrepreneur or in functional expertise or industry expertise, we consider that major pluses as we evaluate the potential success of that entrepreneur.

2. Is the entrepreneur coachable?  We don’t believe you should do whatever we say.  In fact, we don’t think you should do most things we suggest.  However, we think great entrepreneurs are always striving to be better and looking to solve problems.  Often when we bring up issues or questions, the entrepreneur may get very defensive or argue a counter position right away.  The best entrepreneurs are those that listen and take time to process the suggestion or question raised and are not afraid to say they were wrong or “I am going to look into that.”.  As investors, we want to help and if we feel like we are constantly being deflected instead of being treated as a partner, it usually doesn’t end up well.

3. Would you work for them?  This may be the most important trait of them all – the entrepreneur’s ability to hire.  There are three main responsibilities as CEO.  The first, you need to set the Company Vision.  Second, you need to make sure there is money in the bank.   Third, you need to Hire and Retain great talent.  When we evaluate the entrepreneur, we know that the Company is not a one man show.  Its success is based on the people that work there and being able to recruit A talent is a necessity.  Our test is to just ask ourselves “Would I work for them?”.  When you find great entrepreneurs, they have a level of magnetism that compels you to the point where you can envision working for them.  It’s based on charisma, sense of trust and a feeling that the person is a shooting star and you want to grab the tail of that comet and go along for the ride.  When you see that, you know that the person will be able to build great teams.

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Hire Uncomfortably!

When I started Community Connect Inc., I was 23 years old and my only job after graduating college was working at Merrill Lynch as an Investment Banking Analyst for 2 years.  I had never managed someone yet in my career and therefore never learned how to hire well.  I was recently reading the annual shareholders’ letters by Jeff Bezos and in the letter reviewing 1998 he writes the following:

During our hiring meetings, we ask people to consider three questions before making a decision:

Will you admire this person? If you think about the people you’ve admired in your life, they are probably people you’ve been able to learn from or take an example from. For myself, I’ve always tried hard to work only with people I admire, and I encourage folks here to be just as demanding. Life is definitely too short to do otherwise.

Will this person raise the average level of effectiveness of the group they’re entering? We want to fight entropy. The bar has to continuously go up. I ask people to visualize the company 5 years from now. At that point, each of us should look around and say, “The standards are so high now — boy, I’m glad I got in when I did!”

Along what dimension might this person be a superstar? Many people have unique skills, interests, and perspectives that enrich the work environment for all of us. It’s often something that’s not even related to their jobs. One person here is a National Spelling Bee champion (1978, I believe). I suspect it doesn’t help her in her everyday work, but it does make working here more fun if you can occasionally snag her in the hall with a quick challenge: “onomatopoeia!”

When I reflect on how I hired, I focused much more on  the question “Can this person do this job well?”.   However, I tended to hire people that didn’t intimidate me.  Meaning I avoided hiring people that were so smart, talented and knowledgeable that there was not much I can do to teach or instruct them on.  As a first time CEO and manager for that matter, I avoided those type of hires because I wanted to feel like I had full control.   It was like being a first time pro basketball head coach and then having Michael Jordan on your team.  Do you think being a first time head coach and coaching Michael Jordan would be a bit uncomfortable?  Definitely.  This insecurity pushes us to hire comfortably instead of what would be truly best for you as a manager or for the company.

The first time I hired uncomfortably was when I hired Court Cunningham as COO of Community Connect.  Court had more experience than me and is both an amazing strategic thinker and operator.  Court later went on to run Yodle which has been a very successful local marketing services company based here in NY.  Having Court around elevated my game because he pushed me in ways that I had not been pushed in the 8 years prior running the business.  I learned a valuable lesson at that point.  If you are not hiring uncomfortably, you are probably not hiring well.

I have a friend that was recently promoted to manage a team at a large media company.  She recently hired someone senior at her team and she said that she was intimidated by him because she said “he can probably do the job better than me”.  I told her hiring uncomfortably was a demonstration that she was hiring well which is one of the most important attributes in being a great manager.  As an investor, I see this hesitancy happen all the time with first time entrepreneurs.  To be a great entrepreneur, you need to embrace hiring uncomfortably and push your managers to do the same.  By doing so, you will constantly raise the bar and create an environment of excellence.

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To Be a Great Start Up, Set Up Your Core Values Early!

So you launch your start up and you are more than busy ever in your life with tasks such as delivering an MVP, establishing product market fit and speaking to potential investors.  The last thing that you are thinking about is putting together your Company’s Core Values.  Core Values are essentially a formalized description of your company’s culture.  What’s the rush in doing them now?  Aren’t they for big corporations?  Like Tony Hsieh of Zappos has reflected, putting together Core Values should be done at the beginning.  They are the guiding principles on how you plan to run your business.  How you and your co-founders work together, who you hire and how you treat your customers are all based on your Core Values.  You need to make sure it is clear what they are and are adhered to.  It was not something we did at Community Connect until 5 or 6 years after we started the company.  Not only did we do them too late but in really reflecting on it, we didn’t do a lot of things right in putting them together.  In working with start ups, I have a couple guiding principles in putting together Core Values:

1. They need to be incredibly important.  The rule here is that you need to be able to hire and fire based on your Core Values regardless of performance.  So for example, you may have an incredible mobile app developer which finding is like finding a unicorn.  However, if she/he doesn’t live up to any of your Core Values you need to fire that person right away.   Is that hard?  It should be.  That’s how big of a deal these Values are.

2. They need to inspire.  Be careful here.  You need to make sure  that they don’t get watered down and sound incredibly generic and corporate like “Teamwork”, “Integrity” and “Excellence” .  Zzzzzzz…..oh sorry, I fell asleep just writing them out.    Your values need to inspire and ideally feel different.  Think about what makes a cult a cult.  It is a group of people that is inspired by certain values or beliefs which they feel are different from how others think.  If you can get to a cult like level……you just crushed it with inspiration!

3. Ideally 3.  No more than 5.  Look.  Good Christians can’t even remember all ten commandments.  They do remember a few of them like “Thou shall not kill” and that was probably more important than “Remember the Sabbath day”.   So limit them to the few that most people can remember.  If people can’t remember then what is the point of having them!

4. Run Your Company on Them.  Always ask yourself in your hiring process and employee feedback or performance reviews whether or not the person lives up to your Core Values.  If you are not sure, make sure you find out.  Having just one person at your company who doesn’t live up to your Core Values will completely compromise your company culture.   This is a real discipline and needs to be driven by example from the top.  Bom Kim who is the founder and CEO of Coupang is the best entrepreneur I have ever worked with.  One of the key reasons why is that he is so disciplined at adhering to the Core Values.  I have talked to him about certain people that I thought were smart and talented and he would not have them in his company because he won’t risk compromising the culture at Coupang.  If your employees are making a Harlem Shake video (in Korea by the way) and feel compelled to put up signs of the company’s core values……I think that is a sign that you did a really good job.

When joining High Peaks Venture Partners, I realized that Core Values for the firm were never established.  Brad and I agreed that we need to have them in place as the basis of how we run the firm.  We did it with the entire team collaboratively and since then have used it incredibly often as we reflect on the direction that we want to take High Peaks.  Here are our Core Values:

1. No A–holes

2. Be the First Call

3. Do the Work

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The Things We Think and Do Not Say

Who had I become? Just another shark in business casual wear? Two days later after yet another demo day from yet another accelerator, a breakthrough. Breakdown? Breakthrough. I couldn’t escape one simple thought: I hated myself. No, no, no, here’s what it was: I hated my place in the world. I had so much to say and no one to listen. And then it happened. It was the oddest, most unexpected thing. I began writing what they call a mission statement. Not a memo, a mission statement. You know, a suggestion for the future of our company. A night like this doesn’t come along very often. I seized it. What started out as one page became twenty-five. Suddenly, I was my father’s son again. I was remembering the simple pleasures of working at a start up, how I ended up here after hating investment banking, the way you feel when someone tells you that they love what you built. The way we are meant to feel when creating something new and adding value to the world. With so many deals, we had forgotten what was important.

I wrote and wrote and wrote and wrote and I’m not even a writer. I was remembering even the words of the original NY angel investor, my mentor, the late great Dickie Fox who said: ‘The key to this business is personal relationships.’ Suddenly, it was all pretty clear. The answer was fewer portfolio companies. Smaller funds. More attention. Caring for them, caring for ourselves and the industry, too. Just starting our lives, really. Hey – I’ll be the first to admit, what I was writing was somewhat touchy feely. I didn’t care. I have lost the ability to bullshit. It was the me I’d always wanted to be. I posted it in the middle of the night and tweeted about it, facebook shared it and even instragammed the post. I even photoshopped an image that looked like the cover of  The Catcher in the Rye. I entitled it ‘The Things We Think and Do Not Say: The Future of Our Business.’…Everybody could see it…I was 39. I had started my life.

The truth about the Venture Capital industry……it is broken.  There, I said it.  For those of you think VCs make a lot of money…..think again.  Almost all VCs really don’t make that much money because the performance has been lousy.  Don’t believe me?  Look at this post by Fred Wilson.  Venture Capital has been a shit asset class.  Why is this?  It’s pretty simple.  Venture Capital provides little more than money.  Start ups are begun primarily by first time entrepreneurs who face immense challenges and need tons of help and frankly VCs really don’t offer it.  I was asking a well known entrepreneur turned VC what he thinks.  He said that “VCs go at their jobs like they are chasing pu**y”.  All they care about is getting the next hot deal.  I knew this.  I raised $20 million for my company that I started and couldn’t believe at 23 years old I raised all this money and left to figure out what to do all by myself.  I would be lucky if I spoke to my VCs for more than 5 hours a year.  And when I did, they weren’t thinking about me after.  They were out chasing the next deal.  As a fellow entrepreneur once said to me  “The CEO job of a start up is the loneliest job in the world.”  Why are entrepreneurs not demanding more help?  Why are VCs not insisting on being more helpful? We only have ourselves to blame.  We have come to accept this behavior and our industry will crater beneath our feet.

I want to change this.


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Venture Capital Apprenticeship Opportunity

*Update – we received an amazing but overwhelming response.  We are no longer taking any applicants.  Thank you.*

High Peaks Venture Partners is an early stage venture capital firm based in New York City.  We are seeking Associates to work  at minimum 20 hours per week to work along side Partner, Ben Sun.  This is a 4 month apprenticeship.  Ben is a serial entrepreneur having started his first company, Community Connect (published, and  which had a successful exit in 2008.   Since then Ben has invested and/or helped start a number of companies including CoupangHowAboutWeYipitKontagentFundedBuyThinkNearPlum DistrictJump Ramp Games, DerbyJackpot, BounceExchange and Noom.  Ben has recently joined High Peaks as a Partner with a focus on leading investments in the E-commerce sector.  Recent investments include Fashion Project and Greats.

So what are you going to do:

  1. Sit in Company pitch and due diligence sessions and take copious notes.
  2. Participate in the discussion of our assessment of those investment opportunities
  3. Help gather follow up market information, competitive data and other due diligence items
  4. Enter information in our CRM system
  5. Help with Deal write ups for the Partner meeting reviews
  6. Assist portfolio companies – hiring, networking, researching best practices, getting market intel, etc.
  7. Learn a ton!
  8. Network like crazy!

What you get out of it

  1. A great learning experience.  Ben takes mentorship very seriously and will make sure that this is an incredibly rewarding experience if you put in the effort!
  2. Help with pursuing a career in venture capital or working at a great start up
  3. Sorry this is not paid but will definitely help you seek other opportunities across our network of other VCs and Start Up Companies when your internship with us is over.


  1. Strong business acumen.  Ideal candidates come from an investment banking, business consulting or operating background.  A strong interest in E-commerce really helps.   This is beyond having an Amazon Prime account!
  2. You love being in the trenches.  Need to be able to dig in to a business and understand industry dynamics and can find the devil in the details.
  3. You work hard.  Hustle is your middle name.
  4. You are not an A—hole.  You might be a superstar genius but if people don’t always refer to you as a “really nice person” then you definitely don’t belong here.
  5. You figure sh*t out and can work independently.   We don’t need to hold your hand to figure out what you have to do next.

Timing and other details

  1. Need to hire ASAP.  Will last at minimum until the end of the year.
  2. Need to come in one full day per week.  These are days designated for company pitch sessions to the firm.  Our office is at Charlton and Varick in West Soho.

Email me your resume or LinkedIn Profile link at

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