Rare Finds: Looking for Jagged Resumes

I love building teams. Whether it’s helping friends at a startup find the key players that they need to grow or hiring people for my own team, one book I recently read entitled “The Rare Find” takes a contrarian approach to hiring that I wanted to share a few lessons learned. It was recommended by a long-time friend/VC, Nathan.

The book introduces the concept of “jagged resumes” as something hiring managers should focus on when looking for talent. Jagged resumes are people who may have taken a not so direct path to get to where they are today.

They do not tick off all of the traditional checkboxes such as brand-name school, prestigious internships and well-admired employers. It makes sense intuitively because if you’re looking for greatness, you have to look where other people aren’t looking.

As the book recommends, one way to find these people is to look at your own background and pattern matching from there. For example, it could be a shared university course that is known to be the most grueling, a love for tinkering with electronics/computers at a young age, or a hustle mentality (the proverbial kid who not only set up lemonade stands but was able to persuade his friends to come work for him), etc.

The reason you want to find people with jagged resumes is because when you’re hiring, you should be aiming not just for good and risk-mitigation (which is the default mode at many large companies), you’re looking for great.

Another point that resonated is to look for heuristics. The best basketball scouts can be watching thousands of young recruits a year and miss out on a few key players, but by and large, they have honed in on some ways to identify promising players that go beyond the stat line.

Having been a basketball lover since the age of 5, I can’t agree more with how one of the top scouts looks for winning players. The heuristic he employs when watching a game is to microscopically scrutinize a player’s attitude during a timeout or when a ref makes a call that a player doesn’t like, how does it affect the player? “Watch that player more closely on the next play, especially if he accidentally dribbles the ball off his shoe. The best players will regroup and shrug it off. Other players can’t do that. Their temper will get hold of them. You have to take them out of the game for a few minutes.”

The last thing that resonated with me is that the definition of work ethic differs across every industry and job function. It’s easy to forget this and to impart the virtues of one job and apply to a completely different job. I’ve found that this approach tends to be misguided – for example, applying an athlete’s type of work ethic to a job that doesn’t require the same level of competitiveness or manual training. Everyone wants a coworker that works hard. But ask yourself, “what does working hard really mean in the context of the role that I’m hiring for?”

Being an analyst at an investment bank, is actually about working long hours and having attention to detail. In complex sales, working hard doesn’t necessarily equate to that, it’s more about developing a work ethic towards studying everything about the product, your competitors’ product, and how your offering solves a customer need.  In engineering, working hard means being efficient with your time and shipping code.

The reminder here is that when you’re hiring for your next role, keep in mind what work ethic means in the context of the job and look for candidates that signal positively towards this definition.


The importance of tooling

Whenever you have a process that takes your talented team members endless hours to complete, you should always think of ways to help them remove the bottleneck.

One example we recently faced at Skillz which took us longer than desired was Reporting and Revenue Statements. To solve the issue, our team mocked up a new tool to help us revamp the process and shorten the time needed to complete the task by 6x less. That’s hundreds of hours of time saved per year on the account management side when you add it across all team members.

The reminder that as a manager, these are the places you should actively look for to improve upon.

Look at the workflows of your team, what’s taking a freakish amount of time that can be solved by working with your engineering team and building a better tool?

A few places where new tools have been clutch:

– Email to Salesforce functionality
– Email lookup tools, finding lead emails
– Customer service tickets
– Developer troubleshooting tickets
– SCRUM notes
– Event registration software


To do or not to do

Enjoyed this excerpt from Ross McCammon.

“Innovate. Please. The future depends on it. But also: Invent. Because the feature depends on results, too. Things we can touch and walk through. Things we can smell and experience. Services that will change our lives.

Innovation merely ensures that we are working on something. Invention ensures that we are creating what we said we were going to create. We need actuality. We need fulfillment. We need results. And our words need to connote obligation as much as promise.”

Having been in tech for half a decade, there’s more talk than ever before on creating innovative products, but so much of technology are mere solutions in search of problems. Instead, why not commit yourself to the problem and aim hell and high water to solve it?


Deck Making 101: How to make an effective BD presentation

Since many business people spend an inordinate amount of time making powerpoint decks, I thought I’d share a few tips I’ve picked up over the years. It’s remarkable how in today’s day and age, we still rely on having a slideshow to pitch major ideas. It’s a skill that’s pretty underrated, and one that you might as well master through experience. I’ll keep updating this as I think of more.


  • Always try to limit the slide to 1 idea and 3 bullet points if possible
  • Use active verbs (e.g., Launch, Test, Review as opposed to Open, Check, See, etc)
  • Try to only have 2 text sizes in the slide (Header and body text)
  • Make sure everything is aligned, powerpoint comes with an auto-align tool
  • Use the grouping function to move groups of images together without hitting shift + image over and over again
  • Always cite your sources (even if it’s with a little asterisk)
  • Imagine the person looking at your presentation is going to only have time to see the first 1-3 slides, would the presentation still win them over?
  • Have an appendix section that is packed with answers to FAQ’s

Tell a story:

  • Each slide should enable you to tell a story
  • One narrative strategy of the best stories are ones that convey where someone was, where they are now and where they will be
  • Consider using a timeline, gantt chart or graph to tell a story
  • A slide should be able to stand on its own meaning that if you weren’t there to present it, someone should be able to understand the meaning of the slide without commentary
  • This is because most decks are sent after a meeting and you want to assume your listener hasn’t taken notes

Deal Slide:

  • Always have a partnership/deal slide when going into a meeting. It presents the meeting with a natural close and answers the “So what are the next steps?” for your audience
  • The partnership slide should focus on making a test simple and not involve complex negotiation
  • The spirit of the slide should be all you have to do is this little and you get ALOT (in terms of revenue, audience, etc)
  • Use company logos


  • Use transparency effects to give the slides more depth
  • If something is a 3-step process, visually convey this with 1, 2, 3
  • Have eye candy visuals that combine a potential customer’s visual assets with your software, increases the odds of getting a deal done. They want to see how it will work with their system/game/product
  • Mockup visuals for large customers are essential

Creativity is execution

Just wanted to share a little anecdote from two years ago that I think describes creativity quite well.

It was Super Bowl Sunday and my friends and I had skipped off to Maine for a ski trip. We had a total of 20 people staying in the cabin that we rented for the weekend. Many of us were excited to watch the big game but there was a problem: the TV in the cabin was stuck on a single channel.

Naturally, everyone banded together to try and figure out a solution. The diversity of all the possible solutions being thrown around the room (and the way each person handled the problem) presented a nice case study into creativity.

Some of my friends decided to go out to a local electronic store (Best Buy, etc) to try and track down a replacement remote for the TV. Others decided to tinker around with the TV and find a way to hack the schematic/controls in order to change the channel. Both attempts proved futile with all the surrounding stores closed around the area and the TV with no way to change the channel without a remote. A few others became frustrated and decided to tackle the problem by going to a bar instead to watch.

After much deliberation and a few hours later, the game was about to start and no one yet had a solution that would allow us all to watch the game together in the cabin.

I wanted to watch the game and came up with a solution by breaking the problem down into the simplest form. The key to all of this is getting a remote but how did we know which remote? Even if a store was open, the remote we bought wouldn’t work with 100% certainty. Wouldn’t people who lived in the same neighborhood have a remote that would be compatible with this TV?  Likely so. They would also likely have the same cable provider.

Not telling anyone, I snuck out into the cold and started knocking on doors. Most people were surprised that I was walking the barren tundra that is a New England winter. The first 4 houses didn’t have a remote but that last one did. I brought the remote back to our cabin and while everyone was staring at the TV (playing the wrong channel), I flipped the button and changed it right as the football was being kicked off. Mouths dropped in disbelief followed by cheers of joy.

Taking this story and extrapolating lessons learned, I’ve found more often than not that creativity is hardly ever a stroke of genius or coming up with a bright idea. Instead, it’s having a simple idea, going out into the cold and knocking on doors.


Hitting Send – Guiding Questions for Writing Better Business Emails

“Don’t worry if I write rhymes, I write checks” – P.Diddy

A big part of getting deals done boils down to sending the right email.

It seems almost trivial at first, but upon further reflection, this is actually one of the most important things you’ll need to master if you’re hoping to acquire early customers for your company.

For anyone who spends a lot of time thinking about the perfect way to word an email, having a list of key questions to mentally go through can make the difference between a response and radio silence.

Here is a checklist of questions that I’ve found useful right before I think about hitting the Send button:

1) Benefit Focused: Is the email customer centric? Is each sentence phrased in a way that is useful information for the reader? If the reader was thinking “So what? What’s in it for my company or me?” after each paragraph of your email, would the “So What” be answered?

2) Tone: What is the tone that I want to convey? What do I want them to feel after reading it? (Examples include urgency to act, grateful for your help, relieved, etc)

3) Desired Result: What is the targeted advance? (Will this help me get to a further stage such as green light from the decision maker or help towards another important step in the process?)

4) Anticipating the Response: What is the next desired step to take after sending this email? Can I preempt any objections with this email? What are the red flags or FUDs (fear, uncertainty, doubts) that I hope to uncover with this email and can I ask directly to uncover them or find a way to address it in the next meeting? (Examples: who will be in the meeting? What is the agenda and can I prepare ahead of time to set the agenda of the call/meeting)

5) Timing and Brevity: When do I want to send this email? Is there a better or more opportune time? Is the email phrased in the most concise way possible while still hitting all the goals above?


Startups & Fear

To the critic, startup is a noun. To the entrepreneur, startup is a verb.

This piece of wisdom is adapted from a recent book that I read (which I really enjoyed and highly recommend), called Art & Fear – compliments of a Hacker News thread on best books in 2014. The book is one of the most comprehensive descriptions of what it takes to create art and understanding the artists’ emotional journey. It speaks volumes on how to achieve anything difficult, (whether it is sports, tech, art, business), and I found it highly applicable to the journey that entrepreneurs face.

My personal interpretation is that whenever you hear someone critiquing a startup idea, they are observing the idea as a finished product whereas most successful entrepreneurs view their product as a work in progress, something which they constantly look to improve on a daily basis. What matters is whether or not they are getting better at the process.  In short, I think the metaphor rings true, a startup in the eyes of an entrepreneur, is an active verb and never a concrete noun.