Slug it out

Slug it out

“Spend each day trying to be a little wiser than you were when you woke up. Discharge your duties faithfully and well. Step by step you get ahead, but not necessarily in fast spurts. But you build discipline by preparing for fast spurts. Slug it out one inch at a time, day by day. At the end of the day-if you live long enough-most people get what they deserve” – Charlie Munger

Startup Thoughts

Startup Thoughts

I have quite a few ambitious friends who have graduated for a few years now and are in finance or consulting want to start getting into tech, specifically earlier stage companies. Being at a single startup for nearly 4 years now, I thought it would be helpful to share a few lessons learned as it pertains to thriving in an early-stage environment. The common problem that I’ve seen is that many of them don’t fully understand what it takes to (1) break into the industry and (2) to thrive in the role. I thought it’d be helpful to shed some light on the day-to-day of growing a startup as well as recommend a few books I like on the subject. 

Get operational

To join a tech startup, many people want to do the sexy stuff and be in a strategy role or management role right from day one. However, you’re going to find yourself hitting barriers during the interview process as your existing resume is full of internships at great companies that can be interpreted as risk averse decisions that translates into a lack of transferable skills for a startup.

My advice is to focus on the core skills that you want to develop and learn as opposed to being obsessed with chasing a specific industry or company. 

In addition, you need to spend 20% of your time learning skills that will make you more deadly from an operational perspective. Common skills include learning sales + marketing, specific technical knowledge, SQL, hiring, and understanding the customer life cycle. 

The best book I’ve read on this lately is by DuckDuckGo’s founder, Gabriel Weinberg entitled Traction.

Earn vs. Learn

Most people don’t make the right earn vs. learn calculation properly when they are looking to join a startup. The reason is because they are not prioritizing the learning potential of their first startup.

The common question I’ve found helpful to ask is: who are the smartest people that I have access to who are hungry and want to teach me the specific skill that I’m looking for? 

Alignment of motives is very important and this is why having a mentor is not enough. A mentor is someone who you can touch base with once a month/quarter/biannually but not someone who really has skin in the game to see you succeed. They will offer you recommendations but at the end of the day, whether you are successful or not doesn’t really matter to them because your fates are not tied together. In addition, as Sam Altman once pointed out, a lot of advice that you’re getting is someone’s past experiences based on a completely different sort of circumstances and they are not really with you in the trenches trying to solve the problem.

Grit and Politics

The amount of grit it takes to go in day in and day out to not only start a company but to help scale it. This is another skill that I see people who come from less operational roles being less able to pick up from day one. You need to understand that in most cases, you’re making a sale internally to multiple people within your organization and there is a network of decision makers and end-users that will need signoff. Not to mention that you’re not looking just for signoff but whatever project you’re championing to thrive and be successful. I highly recommend picking up a book such as Influence by Richard Cialdini on how to become better with this skill as it is not something anybody is born with right off the bat. 

On the subject of building great teams, this reminds me of an excerpt from one of my favorite basketball books, Bill Simmon’s The Book of Basketball in which he explains that the secret to basketball success isn’t just about talent but talent management. Are players willing to sacrifice for the good of the team? Specifically for a startup facing initial success, how well do you handle the “disease of more”?

Highlighted below: screen-shot-2016-10-24-at-1-25-53-pm

When it comes to grit and persistence, the only real tip I have here is to set yourself up in the mindset where you are activity focused as opposed to just worrying about the results. Focus on your daily, weekly, monthly activities and the end results will follow. My favorite book on this subject is by Bill Walsh (legendary SF 49ers football coach) entitled “The Score Takes Care of Itself.”

Thanks to Yvette for the inspiration for the post!

Thought of the Day

Thought of the Day

“In truth, there is no such thing as a growth industry. There are only companies organized and operated to create and capitalize on growth opportunities. Industries that assume themselves to be riding some automatic growth escalator invariably descend into stagnation.”

—Theodore Levitt

Pockets of A Players

Pockets of A Players

“I observed something fairly early on at Apple, which I didn’t know how to explain then, but have thought a lot about it since. Most things in life have a dynamic range in which average to best is at most 2:1. For example if you go to New York City and get an average taxi cab driver versus the best taxi cab driver, you’ll probably get to your destination with the best taxi driver 30% faster. And an automobile; What’s the difference between the average car and the best? Maybe 20% ?  The best CD player versus the average CD player? Maybe 20% ? So 2:1 is a big dynamic range for most things in life. Now, in software, and it used ot be the case in hardware, the difference between the average software developer and the best is 50:1; Maybe even 100:1. Very few things in life are like this, but what I was lucky enough to spend my life doing, which is software, is like this. So I’ve built a lot of my success on finding these truly gifted people, and not settling for ‘B’ and ‘C’ players, but really going for the ‘A’ players. And I found something… I found that when you get enough ‘A’ players together; when you go through the incredible work to find these ‘A’ players, they really like working with each other. Because most have never had the chance to do that before. And they don’t work with ‘B’ and ‘C’ players, so its self policing. They only want to hire ‘A’ players. So you build these pockets of ‘A’ players and it just propagates.” – Steve Jobs

Rare Finds: Looking for Jagged Resumes

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

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

Managing Complex Change

Managing Complex Change

Screen Shot 2015-08-19 at 8.43.28 AM

Found this flow diagram useful for thinking about the necessary steps for leading a large organizational initiative. I especially like how the chart shows the unintended consequences when one of puzzle pieces is missing.

To do or not to do

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

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