Five-tool Players

I loved Moneyball (the movie).  I also especially love sports analogies as they relate to technology and startups.  While well-blogged about (Fred WilsonDave McClureDharmesh Shah), I believe these analogies are representative of what it takes to create and build a successful startup.  While the premise of the book is to evaluate players based on data and metrics, I couldn’t help but tie back to the old school style of scouting in baseball to the current process we’re going through in selecting our cohort.

According to Wikipedia, in baseball, a five-tool player is one who excels at (1) hitting for average, (2) hitting for power, (3) baserunning skills and speed, (4) throwing ability, and (5) fielding abilities.  I believe the same can be said for entrepreneurs.

Sweetest Swing in Baseball

Hitting for Average : Selling to Customers

In Moneyball, Billy Beane and his sidekick focus their team (the Oakland A’s) on one thing – getting on base – because getting on base equates to scoring runs, which equates to wins.  In the startup world, scoring runs is the equivalent of getting cash, and this cash comes from customers.

Every entrepreneur needs to sell to customers.  They need to generate revenue aka cash.  It doesn’t matter if its enterprise customers, direct to consumer, professional services, white labeling, etc.  Ultimately, if the startup is successful, they will sell to customers (which could also mean acquiring users).  Effective hitters know where to hit the ball – pulling the ball, going opposite field, hitting gaps.  Effective entrepreneurs know the gaps in the market amongst their competition and capitalize.

Hitting for Power : Selling to Investors

Chicks dig the longball.  So how do you generate a huge amount of cash for your startup in one shot?  You sell to investors.  Entrepreneurs should also be able to successfully pitch VCs, angels, and other shareholders.  This gives their companies cash in normally larger amounts than when selling to customers.  It takes a special person to be able to raise from VCs.  It takes a lot of time, energy, and follow-through.

A note on specialists here.  In baseball, there are power hitters that specialize in hitting homeruns.  Traditionally, these are the most popular and most sought after players because they have a halo effect around them.  They fill seats, sell jerseys and advertising.  They are the top billers and they usually can do no wrong (unless they cheat).  In startups, this is also true because some franchises (VCs) want their own cleanup hitters at the top for the same halo effect.

Baserunning Skills & Speed : Hustle, Agility, and Speed

Running the bases in baseball is critical.  If you can’t run the bases effectively, you’ll hinder your ability to score runs.

In startups, it’s critical to have that hustle and agility.  This is all about opportunity maximization once the ball is in play.  This means stretching a single into a double (crosssell / upsell, bigger contracts), stealing when possible (customers from your competition), and generally reading your competition in real-time (intuition and nuances of selling to both customers and investors).

Throwing Ability : Teamwork

This relates to the internal aspects of a startup.  Can you lead and work within a team?  Can you hit the cutoff man e.g. delegate when is the right time to do so?.  This is about being affective with players on your own team to maximize the position you play.  The most effective early stage startups I’ve come across have a good team rapport and play to each others’ strengths.  Especially early when there is generally chaos, playing the position you’re best at (product, sales, marketing, customer services, QA, IT, etc.) and knowing your limits is critical.

Fielding Abilities : GTD

Every entrepreneur can get things done, and similarly every baseball player can catch a flyball or field a grounder.  But the gold glove entrepreneurs are the ones that excel at cranking things out and simply getting things done across a broad range of domains.  JFDI (thanks @msuster)!  To borrow an American football analogy, this is the blocking and tackling that is the unglamorous and often overlooked aspect of entrepreneurialism.


There are definitely other things that make a successful baseball player and entrepreneur – experience, drive, fire, luck, durability, clutch ability, personal circumstances.  Most things have to align for someone to be in the big leagues in baseball and technology.


Over the last year as a VC, I’ve seen a lot of entrepreneurs with different combinations of these tools.  Some were very effective at selling to customers, but just could not raise a round from VCs.  Their pitches were too technical, they got into the weeds too much.  They needed more sizzle.  They were great at selling to customers, hitting their singles and doubles.  But when it came to closing a round, they only had warning track power and process became that much more drawn out and painful.

On the flipside, there were companies where the only thing the CEO could do effectively was raise VC money.  This left their companies with a lot of cash in the bank and a high valuation.  Now they need to execute and build a product that would attract and acquire customers.  Stay off the roids and start bunting if you need.

We are currently scouting players for our franchise.  Are you a five-tool entrepreneur?  If so, APPLY and come see us at Sprouter today.  We’d love to help you develop into an MVP.

Founders & Funders An Update

I think Jevon and Jonas and Karthik are getting sick of running events with me. Before StartupEmpire back in 2008, I ended up in the Emergency Room at Toronto General for another look at my ticker. This week I ended up in the Emergency Room at Toronto General as we are planning Founders & Funders. I’m ok, I was both times but it does complicate the event planning and invitation process.

“Gentlemen, we can rebuild him. We have the technology. We have the capability to make the world’s first bionic man. Steve Austin will be that man. Better than he was before. Better…stronger…faster.” Wikipedia

So if you feel like you only got your invitation very recently, i.e., today. It’s my fault, I am sorry, I have been out of commission. It’s a reminder that you should do a startup before you need a body replacement.

Founders & Funders

Here is the update on Founders & Funders. It has been almost 2 years since we ran the last Founders & Funders (thanks for noticing William ;-). We are 7 days from the event and we have 35 remaining spots. Unlike past events, we are over inviting and over selling the event, i.e., first come first served. So if you got an invite but were waiting that might be a bad plan…

How to get an invitation?

“Fortune favors the connected entrepreneur.” @jcal7 #trueuniversity via @hnshah

We’re looking for “interesting” founders. Often this means people that we’ve met at other events, as Founders & Funders are relatively small social gatherings. That doesn’t mean it is just our friends, as I’ve been often accused. But it is entrepreneurs that we’ve met, that are building interesting companies, that have interesting traction. Get someone that we think is awesome to refer you. It’s a social hack (just like me).

Connect with other founders

Daniel Debow

We have also decided to include a brief fireside chat with Daniel Debow at this dinner. We rarely do this sort of thing at a Founders and Funders but 2011 was such a great year we thought it would be fun to look back on the ups and downs of Rypple through the years and how they got to their eventual exit, some of which was written about in Forbes this week.

What’s the point?

Jonas, Jevon and I are founders. We are not an event company. We are not a media company. We have been trying to write content on StartupNorth that is relevant to us as founders. Whether we are raising money, connecting with other where we live, finding talent, or growing a business. We generally charge very close to the cost of the ticket, i.e., there are some slight over head costs but we are not collecting salaries or generating revenues. This is an unfortunate hobby. But I know there are world-class founders and companies across Canada and while there are government supported organizations and purported lobby groups, we are just a bunch of founders trying to do the things that we find useful in building our companies.

Founders & Funders is a social event. It is designed to connect with the people writing cheques and making investments on a social level. To talk about startups and technologies and business models without the constraints of a pitch. Will there be pitches, definitely (How do you know when an entrepreneur is dead? They stop pitching). The goal is to have a highly edited dinner party with “interesting founders” and get them out of their usual pitch oriented conversation with VCs.

Whether this works or not is questionable, but it does bring together founders and funders in a social context.

What’s Your Personality Type? Insights for Lean Entrepreneurs

Editor’s note: This is a cross post from Flow Ventures written by Raymond Luk (LinkedIn, @rayluk). Follow him on Twitter @rayluk. This post was originally published on February 1, 2012 on Flow Ventures.

The ancient Greek aphorism “Know thyself” is very relevant to entrepreneurs. Most founders don’t give much thought to how their own personality type influences how well they run their startup. Remember, your reality distortion field distorts yourself too.

The good news is that for the first time since I’ve been building companies, entrepreneurs share a common framework for guiding their startups: the Lean startup. Sure, some people don’t use the right vocabulary and misunderstand Lean. But I find that Lean thinking has permeated the entrepreneurial community, so much so that some founders are following the principles without knowing the term “lean startup” at all.

The bad news is that there’s still a huge gap between the understanding of lean startups and the practice. It’s frustrating to see and I think one reason is founders don’t take into account how their own personalities influence the process. I haven’t seen anyone ask: “How is my own personality getting in the way of being lean?

To help answer that question, I’ve created a list of the top 5 personality archetypes I come across, as well as some things to watch out for if you recognize yourself in one (or more than one) of them:

  • “Smartypants”– You’re very knowledgeable and you want people to know it. You love complexity. You believe that superior intellect and knowledge will close the sale, investment etc.
    • Watch out: you’ll ignore the simple solution (which is often the best one) in favour of something more impressive. You’ll discount what customers say because they aren’t smart enough. You’ll be attracted to innovation vs execution.
  • “Intelligent Architect”– Most engineers have this personality type. You like to build machines and you like it when they work as planned. You like the design phase of projects because there are no customers in the design phase…
    • Watch out: you’re going to be very uncomfortable when your startup is trying to find a business model vs building a product. You can’t architect a solution when you don’t know what the problem is yet. Pivots will drive you crazy because there’s nothing wrong with the code.
  • “The Advocate”– Most sales people (and almost all entrepreneurs) are strong when it comes to selling their vision or advocating what they believe in. In a meeting, especially a brainstorm, you talk rather than listen.
    • Watch out: when you’re trying to find product-market fit, you’d better hone your shutting up skills. You can’t hear your customers’ voices when you’re still talking. You already know your own position, it’s time to listen to others.
  • “The Dreamer”– I saw a pitch deck recently for a hyper-local startup. Great deck, nice screenshots, but within 5 minutes the entrepreneur admitted he probably would never use the product, nor did he think anyone else would. It’s easy to envision success IF everyone used your product. It’s harder to make it so.
    • Watch out: you get excited about building an empire but you have a blind spot when it comes to actual customers and their problems. You’ll overestimate how well your product solves their problems.
  • “Mom and Pop”– One great thing about Lean startups is that founders are getting in close proximity to customers to validate their businesses. Most people start with people they know in their community. If you’re a natural hustler, you’ve probably walked down Main Street knocking on doors and signing up beta customers.
    • Watch out: You’ll hold as proof of your business the fact you signed up 10 restaurants in your neighbourhood. Instead of using (and possibly abusing) them to test your hypotheses, you’ll want to make them happy and get pulled in many directions. Be careful you don’t lose sight of the goal. You’re trying to build a scalable business, not a local consulting company.

Spend a bit of time thinking about who you are. Better yet, ask the people around you and make sure there are no sharp objects close by. There’s no value judgment here. There are no “good” or “bad” personality types. But the sooner you recognize your own personality type(s) the sooner you can get out of your own way.

nosce te ipsum

Editor’s note: This is a cross post from Flow Ventures written by Raymond Luk (LinkedIn, @rayluk). Follow him on Twitter @rayluk. This post was originally published on February 1, 2012 on Flow Ventures.