Quick Decisions

Whenever I interview someone that recently worked at a startup that went out of business I ask them why it failed. How analytically someone answers this question says a lot about them. But the truth is that I'm mostly asking because I'm curious. I want to know what to look out for.

More often than not, the answer comes down to one thing: dysfunctional leadership. More specifically, for some reason, leadership didn't communicate well and couldn't make quick decisions. 

Tomas Tunguz had a great blog post on this topic recently, titled the Challenge of Uncertainty. From the post:

“The management team of a company is a decision-making and productivity chokepoint. Critical decisions flow through them. If the management team ruminates on most decisions, the company’s progress stalls. In a 100 person startup, five slow-to-decide executives limit the productivity of 95 employees. In a 1000 person startup, the ratio might be 10:990. There’s enormous leverage in a hierarchical organization if the leadership moves quickly. The converse is equally true. Sluggish decision-making halts all progress.

The cost of deciding slowly seems small. Just a day or a week of more research; one more experiment. But a day’s delay in a 1000 person organization costs the company more than $400k in lost productivity.”

Slow decision-making can be paralyzing for a company.

Management teams should check themselves occasionally on the speed and quality of their decision-making. It will almost always deteriorate over time. There are dozens of little things that can weigh down management and cause them to slow the pace -- too many direct reports, too many meetings, not enough meetings, new personalities, fear of telling the truth, personal issues, different communication styles, poor prioritization and on and on. All of these things will come up at some point. How well a leadership team weeds through this stuff and finds a way to continue to make good, speedy decisions might make the difference.

Some Advice For People Joining A Tech Startup For The First Time

Joining a tech startup for the first time is extremely difficult. If you’ve come from a big public company or a non-profit or the public sector it can feel really unnatural and even uncomfortable. The way you’ve operated in the past likely won’t work. Things will feel weird.

I’ve had the luxury of working in five different tech startups and have been in a position to see trends around the things successful people do and the things the not so successful people do. Here's some advice based on what I've seen over the years. I hope it’s helpful for people that are joining a tech startup for the first time. 

Be incredibly good at dealing with change. Depending on the number of employees in the startup, headcount can literally double in a month or even a couple of weeks. The number of customers serviced can double. Cash in the bank can grow by 1000x. A crucial employee can quit. A major customer can cancel. Because startups are small, change and its impact can feel radical. The company can become a different company in an instant. This is a strange thing. This doesn't happen in a normal company. In addition, in the early days, a startup is really just a hypothesis about solving a problem. And the way that the company is solving the problem will change constantly. For the employee, this means they are likely to have different bosses and jobs and roles and projects in a short amount of time. Learn to enjoy and thrive in this change. 

In your first 90 days do something awesome. When you join a startup, because of its small size, you’re going to have a lot of eyes on you — particularly from people that can make decisions about your future. Find a way to impress them. Take ownership of a project or a sale or a product or a process improvement and dive in deep and make it great. Be transparent about what worked and what didn’t. You’ll find that failure is generally not frowned upon and learning is highly valued. Doing something awesome is not necessarily easy. It’s not going to come to you. Have zero expectation that someone is going to set you up for success. Go get it and make it happen. 

Avoid playing politics. In larger companies, to get ahead you have to play the political game. This is much less true in startups. In a large successful company an employee can do nothing and play politics and the damage to the company is non-existent. The great employees aren’t playing this game and if you are you’ll stand out. People will pick up on it and you’ll get a reputation as someone that is political and it’ll be hard to shake. Get stuff done and be transparent about your success and learning. The downside of a startup is sometimes if one person doesn’t like you it can hold you back because there isn’t a defined system to move you forward. This is why you should avoid playing politics because it’s a quick way to get people that matter to not like you. The way to be liked is to produce results and share what you're learning.

Think short term and long term. This is one of the hardest things to do. It's not natural but it's necessary. The main thing that is going to get you ahead is your ability to produce short-term results and to be transparent about those results (and your learnings). You have to think short-term and show weekly if not daily progress. But you also want to have a longer-term point of view on your industry and where things are going. Your leadership team is getting paid to predict the future and that's hard to do. They will love the employee that can deliver short-term results but can also act as a thought partner in how the company should be thinking about longer-term strategy.

Make work a very big part of your life. There are times in our lives where we want to focus lots of attention on things outside of work. If you’re going through that time in your life then I’d encourage you not to join a startup. A startup’s cost of capital is generally extremely high. It costs the startup a lot of equity value to raise the capital needed to pay your salary. Because of that, there will be high expectations around your commitment and production. This is a crucial point. It’s simple math. It costs much more for a startup to employ you than it does a big company. And your impact is also greater. If you’re in a 30 person team your contribution, on average, is 1,000 times greater than the same person in a 30,000 person company. The startup is going to rely on you greatly. If you’re uncomfortable with that pressure you’re in the wrong company. 

Be humble. It is enormously difficult to effectively operate in startup if you’re not humble. It almost can’t be done. The way you are doing things today is going to change dramatically because it’s not right. Your product isn’t right. Your pricing isn’t right. Your process isn’t right. Your go-to-market isn't right. You have to have a perpetual curiosity about what can be done better, the humility to recognize it can be done better and the willingness to go out and do it better. If you can’t check your ego and do this well you will fail. 

Hire people that are better than you. When you’re hiring people there’s a temptation to make sure that you’re not hiring someone that can take your job. Do the opposite. Hire people that can take your job. This may not feel natural but I’ve found over and over again that people that are willing to take this approach win because they build A+ teams and that’s much better than the safety that comes from hiring a B team. A+ teams create exponential value. B teams create linear value and in some cases negative value. 

Be insanely commercial. Most startups are not sustainable. If they weren’t taking in outside capital they’d go out of business. Be very aware of this reality. This is not a comfortable situation for the executive team. By definition it’s uncomfortable. Embrace this reality and get onboard with leadership in understanding that it all could come crumbling down. Commercial success is the only thing that matters in the early days.

Challenge yourself to understand context. Because things move so fast and there often isn’t clear ownership and process, decisions made by leadership or other teams may seem dumb. People may seem incompetent. This generally isn’t the case. At one startup I worked in I had the luxury of working closely with the leadership team but I wasn’t on the leadership team. I’d be in the room and see how leadership made decisions and then I’d be out for drinks with my peers and they’d complain about how leadership was clueless and didn't make good decisions. I couldn’t believe what I was hearing. The problem wasn’t that leadership was incompetent, the problem was that my peers lacked the context and lens that leadership was operating under. Challenge yourself to not dismiss seemingly bad decisions as people being uninformed and try to see the decision through the other person’s eyes.

Consider doing the impossible. If you dive into the history of most extremely successful startups they probably did something at some point that seemed impossible. This is true of most major success stories. For some reason, I always think about poker on television. Today, millions of people watch poker on television but there was a time when this was a crazy idea. The reason was that the great players would never agree to have the cameras see their cards during a game. And if the viewer couldn’t see the cards all the drama would be lost. But it was a non-starter with the players. No way. Never going to happen. But some ambitious TV producer saw the opportunity and didn’t accept that reality. He forced it and found a way to get the players to agree and now television poker is a multi-million dollar product. Consider the things that you think are non-starters or are impossible and try to see if you can find a way to break through. Don't be the naysayer. Be the one searching for the solution to the impossible problem. Find a way.

The Issue Of The Day

I’ve found that one of the most important things an executive can do is to regularly identify the “issue of the day” for their company or their team or their group and to address it with urgency.

Peter Drucker refers to this as identifying “what needs to be done?” Ideally, it's one thing, but definitely not more than two.

The discipline to continuously have this in mind and to have the emotional intelligence to be able to accurately identify the issue of the day is difficult and something that separates great leaders from the rest.

The issue of the day could be a number of things: some are opportunities, some are problems, some are strategic, some are tactical, some are elated to business problems, some are related to people problems. An example could be launching a product that will create a large growth opportunity or retain a specific set of customers; onboarding new managers and making them into productive leaders or something as small as fixing a commission policy or plan that is frustrating for top salespeople. The key is the ability to recognize the issue and measure its importance and urgency in comparison to the hundreds of other burning issues that could be addressed.

One of the most difficult things about determining the issue of the day is that different people will often have different perspectives on what the issue of the day actually is. The board, the CEO, the executive team, the line managers will often have different opinions. Getting alignment here is crucial. And, just as important, if alignment can’t be gained across all relevant stakeholders, the executive must make the call on what's most important now and focus on that thing more than any other.

Silo And Un-Silo

Back when I was working at Next Jump, an e-commerce company that enabled big brands to offer their products and services at a discount to large employers and customers of large consumer marketers, our primary objective was to drive spend through our website.

My specific job was to drive user acquisition. I was focused on acquiring more companies to buy the product for their employees and then to get employees (users) to register an account and keep coming back. My colleague, I'll call her Jane, was in charge of site merchandising and had the job of converting those users into buyers once they came to our site. So my job was to get people to our site, and her job was to get people to buy once they arrived.

Every week our teams would meet to review results. We’d start by focusing on the total spend on our site during the previous week. Some weeks the numbers would be up and some weeks they'd be down. In the weekly meeting, our leadership would look at Jane and ask what happened during the previous week. Frequently, Jane would look at me and say, “we didn’t have a lot of spend on the site because we didn’t have a lot of traffic.” Other weeks I would look at Jane and say, "we had plenty of traffic but that traffic didn’t convert into spend."

This was obviously unproductive. We were pointing fingers at one another and defending our impact on the overall number which meant that nobody was responsible for the overall number.  

Our solution to this problem might seem counterintuitive: we created silos.

We came up with something we called “the box.” My team had the job of getting people into the box (get people to the site) and Jane's team had the job of making good things happen once they were in the box (get people to buy things once they were on the site). My primary metric was weekly unique users and Jane’s primary metric was conversion of those users (spend per unique user).

This changed everything. We set up specific metrics for each team where neither one of us could ever blame the other. My team wasn’t measured on overall spend (something we couldn’t control alone) and Jane’s team wasn’t measured on overall spend (something her team couldn’t control alone). We were measured on our slice of the spend metric (users and conversions) and if we both did our job we had a great week. This change created crystal clear ownership and accountability which led to lots of creativity and powerful initiatives to drive each teams' numbers. Our overall spend numbers started heading up and to the right.

Over time, though, things started to break down. Because we were so silo’ed my team wasn’t focused on the overall company goal, we were focused on our team goal. So my team would do whatever we could to drive users to the site regardless of the impact on spend. We would repeatedly promote offers from Target and Best Buy (brands that had 'mass appeal’ and would drive traffic but had relatively low value discounts with low conversion rates). This would drive a ton of traffic to the site, but the traffic didn't convert. Similarly, Jane was focused on conversion so she would promote the best offers on the site (30% off Juicy Couture, as an example). Users would come to the site expecting to see an offer from Best Buy and would see a great offer from a brand they had no interest in and a not so great offer from Best Buy. This led to a low-quality experience, lower spend, and user churn. Overall growth in spend began to slow down.

In response, we quickly setup processes to begin working more closely together. We had to fix the disconnect. We had to collaborate.

We built a monthly merchandising calendar that every team member could access in real-time. We set up several 10-minute check-ins so that the acquisition team knew exactly what the site merchandising team was promoting each day and which offers were converting at the highest rates. The acquisition team would send all marketing emails to the merchandising team prior to sending to users to get their sign off. We used data from the acquisition team to convince the mass appeal brands to offer deeper discounts. 

At first, these efforts forced collaboration. But over time the collaboration became much more organic. The teams became inclined to be collaborative. After a few weeks, the numbers started to head back up. That said, we definitely didn’t abandon the silo’ed metrics for each team. Hitting those metrics was still the primary job of each team. What changed was the approach we took to hitting each of our metrics. It was about transparency and collaboration and a broader focus on what was best for the company as a whole.

The point here is simple: not having silo’ed metrics is a bad thing and being too silo'ed is a bad thing.

As an example, sales teams need to have silo’ed sales metrics that they’re accountable for to force ownership and creativity and high performance. But if the sales team is only focused on one top line metric and nothing else, over time they’ll be motivated to close deals that may be bad for the company and will lead to high churn rates. They have to have a silo’ed metric but also be forced to consider what’s best for the company as a whole.

Companies get in trouble when they lean too far towards one side. Telling groups to just work together to drive an overall number leads to a lack of accountability and creativity. And too much separation leads to a lack of collaboration and focus on the broader goal.

Well run companies find a balance and learn to silo and un-silo.

Writing To Learn

Tim Ferris had a great podcast with Daniel Pink a couple weeks ago. I'm a big Daniel Pink fan. I highly recommend reading his book To Sell Is Human. 

In the podcast, Daniel talks about the fact that one of the main reasons he writes is not to teach people something but rather for him to learn something. And often, when he sits down to write about an idea part of the way into it he realizes that the idea stinks. Or that the theory he set out to write about is just wrong.

This really resonated with me. The reason I've kept writing on this blog for more than ten years isn't to tell people things I know that they don't (though if that happens that's great). The primary reason is that I learn through writing more than other medium. If I have an idea or a theory I find it enormously valuable to get it down on paper. I'm no different than Daniel in that I have literally dozens of draft blog posts in my Squarespace account that I haven't published because halfway through writing them I realized the idea wasn't good or was wrong or wasn't fully baked. 

I highly recommend that people write down their ideas on a blog or an Evernote or a personal journal. Writing forces you to focus and think clearly and consider alternatives and ensure that an idea isn't just a whim but a well thought out, actionable concept that matters. The clarity that comes from writing is invaluable.

For me, that clarity has been the best thing about writing on this blog.

How To Know You're Hiring Great People

Recently someone asked me how I get comfortable that I'm hiring great people. Obviously there’s a ton of work that goes into making a hire so I won’t go into all of the detail. But just before I’m ready to pull the trigger there are four checkpoints I use to make sure I’m making the right call.

1. I can clearly point to something about them (beyond functional expertise) that they can do (or I believe they will be able to do) at a world-class level.
2. Credible, smart, successful people say amazing things about them.
3. If I strip away their credentials, I'm still really fired up about making the hire
4. The reason they bounced from one job to the next doesn’t concern me, it inspires me.

There are obviously lots of other things I could add to this list but I’ve found that I'm generally making a great hire when these four things are in place.

Four Productivity Apps

Here are four apps that I've been using recently that have increased my productivity.

Accompany. This app will scour your calendars and see who you're meeting with in the coming days and weeks and will build out a profile for each person that includes news mentions, bios listed on the web and updates from their presence on Twitter, AngelList, Crunchbase, LinkedIn and other social networks. It pulls everything into a one-page profile. Just prior to your meeting it will send you an email with all of these details. Last week I was at the HIMSS conference in Las Vegas and found it invaluable. As I walking between meetings I could read through the manifest for my next meeting and get a refresh on who I was about to talk to. Following the meeting it adds the people you've met to your network and it will continue to push out updates. You can set preferences so you only get updates on people you want to hear about. 

MobileDay. I’ve been using this one for a while but just started using it more often. MobileDay scours your calendars for upcoming conference calls and pulls the conference call dial-in details into the app and pushes you a notification just prior to the meeting so that you can dial into the call with just one click. You just literally just click on the notification and it will dial you in. This is so much better than switching between my calendar app and phone app trying to remember a ten digit number to get dialed in.

Brain.fm is an app that has ambient sounds on a timer that helps with intense focus. I often listen to music when I'm writing but I've found that if I really need to focus on something for a sustained period of time the sounds on Brain.fm work a lot better than Spotify. Note that the app requires you to be online so when I’m on a plane or somewhere without access to the internet I'll use the Noisli app. Not as good but gets the job done.

Astro is an AI-powered email application. It's pretty amazing and I'm not sure I'm getting everything out of it that I could. The more you use it the smarter it gets. It does a great job of building a priority inbox based on the emails you open and the people you email often. And it has a bot that pushes questions to you about your contacts and makes recommendations and reminders to follow up on important emails. It also can track email opens and has a send later feature. I understand that there's a lot more coming as Astro is building a big AI company around the app. The sooner you download this one the better. 

The VentureFizz Podcast

I did a podcast with Keith Cline from VentureFizz a few weeks ago. We talked about my career, how I think about growing startups and lots of other stuff. You can listen to it on iTunes here or on Soundcloud below. 

Welcome to Episode 14 of The VentureFizz Podcast, the flagship podcast of Boston's most trusted source for startup and tech jobs, news, and insights! On this episode, VentureFizz Founder Keith Cline is joined Brian Manning, who is the VP & Head of Growth at PatientPing, a healthcare technology company in Boston. He built out successful businesses at Zocdoc and NextJump, and he’s focused on doing the same at PatientPing, a company backed by leading VCs like First Round Capital, Andreessen Horowitz, F-Prime Capital, and others. In our interview, you’ll hear about Brian’s background, his ability to succeed in a role usually handled by multiple people, his thoughts on creating a growth strategy, and lots more. Lastly, if you like the show, please remember to subscribe to and review us on iTunes, or your podcast player of choice! And make sure to follow PatientPing on Twitter @PatientPing and VentureFizz @VentureFizz.

Asking Good Questions During The Sales Process

One of the best salespeople I've ever worked with wasn't all that great at giving presentations. He wasn't great at building relationships. He didn't know the product as well as others on the team.

So what made him so good? 

He would ask the prospect questions. Lots of questions. I mean almost obsessively. When it got awkward with the prospect because he was asking so many questions he'd ask five more questions.

This helped him sell for several reasons:

1. He fully understood the motivations of the buyer and could tap into those things to keep the deal moving.
2. He fully understood in great detail what the buyer's buying process was and exactly what was needed to get the deal over the line and he could anticipate any bumps in the road.
3. He uncovered things that the prospect didn't know about their own needs or things that exist in their own process that they were unaware of that might slow down the deal.
4. He could uncover trends around problems and solutions inside the prospect's organization that he could leverage across other deals. 
5. He truly got to know the actors involved in the purchase (influencers, blockers, etc.). 

Too often salespeople want to hear good news so when they hear it they don't dig in and ask lots of questions. I learned from my former colleague that it's much better to assume the worst and dig in with good questions to understand and confirm everything. 

Here are some of the questions that can be asked as a salesperson navigates the sales process. As I said, these may seem somewhat obsessive, but because buying things at a large organization can be so tedious and difficult I've found that most buyers appreciate the thoroughness.

1. What are your priorities this quarter/year and do you think this product fits in?
2. How would you explain to someone in your company how this product is going to help you reach your objectives?
3. What are the other projects on your plate and how would you prioritize this one?
4. When we launch this product will you personally be measured on its success? By who? How will it be measured?
5. How do you typically buy products like this?
6. Who is involved in the buying decision?
7. Is there anyone that needs to sign off on this (IT, compliance, etc.)?
8. Is there anyone that you think might object to buying this product?
9. Have you come across any roadblocks in buying these kinds of products in the past?
10. How did you get past those roadblocks?
11. What committees need to see this product before you buy?
12. When do those committees meet?
13. Could we find some time to present this in the next committee meeting?
14. What will each of the people in the committee care most about with regard to this product?
15. Who will use the product? 
16. How will they use the product?
17. Where would the budget come from?
18. Is there enough left in that budget to pay for something like this?
19. What is the process to get the budget approved?
20. What does it take to schedule implementation resources on your side?
21. What specific measures will your company consider when looking at the success of the product after it's been launched?
22. Who will sign the contract? 
23. Does the contract signer need any approvals before signing?
24. Can I be introduced to the contract signer’s assistant to make sure nothing gets missed?
25. Is the contract signer in the office on the day we expect to sign?

I could easily list twenty-five more. Of course, it's worth noting that there is some art to how you ask the questions and the questions should be documented and placed at different stages of your sales process so it makes sense why they're being asked at the time.

I've found that in complex sales a salesperson almost can't ask enough questions. Those salespeople that have the discipline to use good questions to understand the prospect and uncover potential pitfalls significantly outperform their peers. 

Some Thoughts On Apple And Personal Health Records

There was a lot of buzz going around this past week around Apple’s announcement that they're adding a personal health record to the iPhone. 

Of course, this has been tried before; Google, Microsoft, and many, many others have tried and failed. This time Apple has a better shot in that they 1.) have a device in people's hand and 2.) they've partnered with several large hospitals & health systems and electronic health record (EHR) vendors to pull data down to the device.

Bijan Salehizadeh asked the right question on Twitter: did past efforts at consumer-driven personal health records not work because of poor user experience or did they not work because people just don’t care enough about their health records?

I’m in the camp of people not caring enough. Put aside the importance of what Apple is trying to accomplish and the incredible impact it could have if it were successful and get back to the basics of consumer behavior and what makes an iPhone app work. 

In order for someone to choose to spend time on an app (when there are millions of them in the app store) the user needs to get something in return. And they need to get that return quickly. When I search for a restaurant on Foursquare I get a return (recommendations). When I use OpenTable I get a return (a dinner reservation). When I use WhatsApp I get a return (a conversation with a friend). When I use Spotify I get a return (music).

But what does the consumer get when they upload a bunch of health data into the Apple health record? Nothing. At least not immediately. At least not until they’re sick. Which they hope they never are. There's no clear return. This is the challenge with patient-driven health records.

This is part of the brilliance of Zocdoc (disclaimer: I worked there for almost 4 years). They are able to compile important health information from the consumer. Lots and lots of it. Every single day. They’re able to do it because the user gets something in return immediately for engaging and sharing their health information (a doctor’s appointment). 

In my view, the companies that have failed on personal health records have failed because they didn't fully appreciate the way consumers engage with their own healthcare and they ignored the core tenets of consumer behavior. People are busy and have been trained to ignore everything unless it makes them feel good or gives them some near instant utility. Unless Apple's personal health record app can find a way to deliver utility back to the user (quickly) I fear that it may share the same fate as those that have tried and failed.

Time

I recently reread Peter Drucker’s The Effective Executive. The entire book is gold and much of it is centered around the way we manage time. This is how he describes time:

"The supply of time is totally inelastic. No matter how high the demand, the supply will not go up. There is no price for it and no marginal utility curve for it. Moreover, time is totally perishable and cannot be stored. Yesterday’s time is gone forever and will never come back. Time is, therefore, always in exceedingly short supply. Time is totally irreplaceable. Within limits we can substitute one resource for another, copper for aluminum, for instance. We can substitute capital for human labor. We can use more knowledge or more brawn. But there is no substitute for time. Everything requires time. It is the one truly universal condition. All work takes place in time and uses up time. Yet most people take for granted this unique, irreplaceable, and necessary resource. Nothing else, perhaps, distinguishes effective executives as much as their tender loving care of time."

Time is a pretty unique thing. I’ve recently started the habit of evaluating how I spend my time by looking back on my calendar every couple of months. When you’re going from meeting to meeting to meeting all day it’s really easy to think you’re spending your time wisely. I’ve found that I’m often not. And doing a frequent look back helps me change that.

The 10 Best Books I Read In 2017

For some reason I've stopped posting my summer reading lists on this blog. So instead I thought I'd start posting a top 10 list at the end of the year. As I typically like to do I read a lot of business books, history books and biographies. I also read a couple good fiction books but none that make the top 10. Here's the 10 best from 2017, in order:

1. America's Bitter Pill: Money, Politics, Back-Room Deals, and the Fight to Fix Our Broken Healthcare System by Steven Brill. This is a phenomenal chronicle of how the Affordable Care Act came into law. An in-depth summary of the issues in American healthcare and the troubling challenges that come with passing an important piece of legislation in today's environment.  
2. Smarter Faster Better: The Secrets of Being Productive in Life and Business by Charles Duhigg. This is written by the same guy that wrote the Power of Habit, also a great book. This is sort of a business/self-help book but one of the few with actionable, useful insights to transform busy work into productive work. Probably a bit too long due to all the examples, but this one was worth the time.
3. Hacking Growth: How Today's Fastest-Growing Companies Drive Breakout Success by Sean Ellis. This should be required reading for those of us focused on growing early-stage companies. Very focused on consumer businesses but the book is filled with really refreshing "out of the box" thinking that is so important in a high growth company.
4. Dreamland: The True Tale of America's Opiate Epidemic by Sam Quinones. Probably the best-written book on this list, this tells the depressing story of the formation of the opiate epidemic in America. This should be mandatory reading for any politician interesting in fixing this crisis. There is so much context in here that needs to be understood before anyone can think about effective solutions.
5. Why Buddhism Is True: The Science and Philosophy of Enlightenment by Robert Wright. No, I'm not a Buddhist but I've been fascinated by pieces of it for a few years now and I wanted to dig into it a little deeper. This is also a wonderfully written book that gives a great summary and strong defense of the religion's truths. 
6. Extreme Ownership: How U.S. Navy SEALs Lead and Win by Jocko Willink and Leif Babin. Written by two former Navy SEALs that saw enormous amounts of brutal conflict in Iraq and Afghanistan, the book takes the lessons of being successful in war to being successful in business. And these two guys are just incredible human beings. They make a strong case for getting up at 4:30am each morning. Yes, "business is war" is definitely an old euphemism but this book is on point. And it is true that much of what we do in business translates to the battlefield. Jocko also has a podcast that continues the story that's worth adding to your list. 
7. Leonardo da Vinci by Walter Isaacson. da Vinci didn't just paint the two most famous paintings in history he also obsessively studied anatomy, fossils, birds, the heart, flying machines, botany, geology, and weaponry. This is another book that was somewhat too long but understanding more about this man was enormously inspiring.
8. Grit: The Power of Passion and Perseverance by Angela Duckworth. I had read so much about this book prior to reading this book that I really didn't need to read it. But the concept is great. The strong evidence of the fact that grit is the most important trait for one to have is fascinating and inspiring. A good one for parents.
9. The Effective Executive by Peter Drucker. I've read this at least three times and it's always worth it. Timeline insights from the management guru.
10. Thomas Jefferson: The Art of Power by Jon Meachem. I saw Meachem speak earlier in the year and took a look at what he's written. For some reason, I continue to find early American history to be incredibly interesting. This is really a big history book about the formation of the United States. Extremely well written, an in-depth history book. A good one for the beach.

I hope you like some of these recommendations. Happy New Year!