We spent about a week in Spain between Barcelona and Mallorca over New Years. We did more than the below, but here are our recommendations:


  • Stay
    • Seventy Barcelona – Great hotel and location – the breakfast/drinks at the bar are soo good
    • Cava & Hotel Mastinell – 60 minutes outside of Barcelona. The rooms are designed to look like wine bottles. Good experience but not much to do in the area outside of visiting wineries 
    • Fairmont Juan Carlos – we booked here because we had an early flight. Good business hotel, but wouldn’t book if you want to really be in Barcelona
  • Eat
    • Brunch & Cake – Best food of the trip – we went 3 times. Must gets: peanut latte, detox juice, any of the food
    • Cerveseria Catalana – well known place with a huge menu, go early to put your name down, the waitlist can get long
    • Flax & Kale Passage – was hyped but we thought it was overrated
    • Cal Pep – awesome place, sit at the bar and let them order for you
    • La Pepita – right across from the hotel, solid tapas
    • Boldu – good donuts shaped like little people
    • Xurreria Trebol – mmm churros
  • Do
    • BCN Kitchen – Went shopping for the ingredients at a market and then cooked paella. We thought it was just okay
    • BCN Baila – We found a dance studio and set up a private one hour salsa class – was fun!
    • Pares Balta terroir tour – One of the highlights of the trip – wine tasting and off-road drive through the different vineyards on the property
    • Standard tourist stop: Park Guell, Sagrada Familia, Ramblas, etc. If you want to go to a park or museum, buy your ticket in advance.


  • Stay
    • Park Hyatt Mallorca (eastern coast) – amazing hotel, kind of far away from everything which is great to go to the beach but not great if you want to visit towns
    • Sant Francesc Hotel Singular (Palma) – nice hotel in an old family’s house – good location in Palma
  • Eat
    • Ca’n Joan de s’Aigo – ensaimadas are delicious – we were fighting some food poisoning so could not enjoy them in all their glory
    • S’estret – cute and tasty cafe in Valldemossa
  • Do
    • Cuevas Drach – touristy caves, but they are still cool
    • Beaches – beaches are amazing, we went in the winter so there was nobody on them
    • Palma cathedral – nice cathedral, overrated on the inside
    • Valledemossa – really pretty town
    • Inca / Inca Market – waste of time, not worth it

Hawaii Big Island

We spent 4 days on the Big Island in Hawaii. We split up our trip into two areas of the island: Volcano for 2 days and Kona for 2 days. We did more than the below, but here are our recommendations:

  • Stay
    • Volcano – we stayed in an AirBnb – 11-3807 10th Street – Mauna Loa Estates. It had a really peaceful Japanese vibe and was really close to the park
    • Kona – we stayed at the Fairmont Orchid – family friendly with a nice private beach. We liked it but thought it was a better hotel for families than for couples
  • Eat
    • Acai bowls – we fancy ourselves connoisseurs of acai bowls
      • Under the Bodhi Tree – right by the Fairmont. All the food was great, especially the acai bowls, and we ate there several times
      • SF Coffee Company – surprisingly good acai in the middle of commercial area
      • Honai Wai Cafe – amazing acai bowl, best of the trip
      • Makani’s Magic Pineapple Shack – this place gets lots of hype but we thought the açaí was meh, and wouldn’t go back
    • Meals
      • Umeke’s Fish Market Bar & Grill – amazing poke place near the airport
      • Ken’s House of Pancakes – get macnut pancakes, owned by the Rock’s family!
      • Herbivores – vegan restaurant in a parking lot. It was incredible, especially the jackfruit nachos!
    • Malasadas, aka Big Island donuts
      • Punalu’u Bake Shop – down at the southern tip. Get there early because they sell out. We picked them up on the drive to Volcano from the airport
      • Tex – Well known place. The secret we found was to do the drive-through vs. wait in the line inside. Also get the plain, the filled ones have a lot of filling
  • Do
    • Beaches – you can’t go to Hawaii without going to the beach
      • Punaluʻu Beach – black sand
      • Beaches on the Kona side of the island are great, especially the beach by the Mauna Kea Beach Hotel
    • Hikes – there are a lot of great hikes around the island, especially in Volcano National Park
      • Our favorite was Kilauea Iki Trail – Kate actually did this hike twice
      • We also visited Akaka Falls State Park, which was more of a walk than a hike, but takes you to a giant waterfall that’s pretty cool to see 
    • Manta Ray Advocates – this was the best thing we did. You go snorkeling with manta rays. We went on a six person tour that is focused on manta ray conservation (vs. a large tour groups which can disrupt / harm the animals). Definitely do this!
    • Hilo farmer’s market – popular but we felt it is overrated 

Croatia / France

Kate and I spend so much time planning our vacations and we get asked about them frequently, so I’m going to start creating blog posts for where we stayed and what we did so it’s easy to share. We just spent 12 days in Croatia and Paris. Here are our notes:


  • Stay
  • Eat
    • Gusta me – just outside the city walls on the walk to the cable car. I think I liked it more than Kate – the tuna, fish, and house wine were great
    • Dolca Vita – great gelato place – went 3 times in 2 days
    • Taj Mahal – Bosnian food (read: meat), solid, but not as good if you get the meat sweats while walking on the city walls in the heat
  • Do
    • Climb the city walls – we went in the afternoon – it was really hot but less crowded because it was so hot
    • Cable car to see the city – go at sunset
    • Sunset kayak tour – crowded but still fun


  • Stay
    • Hotel Jagodna – 15 minutes outside of Hvar town on a beautiful bay where you can swim. Rooms are basic but it’s awesome.
  • Eat
    • Antika in Stari Grad – best meal of the trip.
    • Fig Hvar – went there twice in 2 days. Amazing fig flat bread. There is also on in Stari Grad and Split in case you miss it here.
    • Konobo Menego – Croatian food on your way up to see the fort. Get the octopus salad and the gnocchi
    • Hotel Jagodna – great dinner – fish is amazing
  • Do
    • Visit Stari Grad – outside of Hvar town but cute small town. It’s one of the oldest towns in Croatia and Europe
    • Rent a boat (that you can drive) and cruise the seas
    • Do the walk up to the Spanish fortress


  • Go here and stay at Hotel Lemongarden and do / eat everything they let you. It’s expensive but totally worth it.


  • Stay
    • Did an AirBnB but didn’t spend much time in it
  • Eat
    • Fig Split
    • Corto Maltese – creative Dalmatian food. Good drinks (especially lavender gin and tonic) and you can sit on the street and people watch
    • Ciri Biri Bela – Similar to Plant Cafe. We didn’t love it but it was probably just because it was so hot.
  • Do
    • Rent a car and go to Krka waterfalls – amazing. Make sure to go early, it gets really crowded with tour groups starting at about 10am
    • Diocletian Palace – we didn’t actually go in but it’s nice to look at from the outside


  • Stay
    • Le Bristol – place is amazing but really expensive. Thanks to Kate for getting a great rate through work
  • Eat
    • Croissants – favorites were Boulangerie Alexine and Miss Manon
    • Soul kitchen – right behind Sacre Cour, seemed to have only locals and food was cheap and delicious
    • KB coffee – oat milk cappucinos
    • Cook n Saj – loved this place. Family run Lebanese that was yummy, fun, and affordable
    • Arc de Falafel – in the guidebooks. The line is long but it’s cheap and really filling
    • La Drougerie Du Marais – crepes by the falafel place. Solid.
    • La Portena – empanada counter – aka a place made for me
  • Do
    • Eiffel tower
    • Ateliers Lumieries – really cool art museum that has 20 minute experiences. We saw the Van Gogh one and really loved it
    • Montmarte – really cute neighborhood with Sacre Cour, artists, and great food
    • Rent electric bikes and bike along the Seine – do it in the morning and on the weekend. The city gets really crowded and dangerous to bike later in the day. Make sure to dodge the scooters.

New Year, New Post

Hello everyone and welcome to 2018! It’s going to be an exciting year.

I’ve kicked off the year by writing a bimonthly column for YourStory (, the TechCrunch of India. My goal is to answer questions from Indian entrepreneurs and share my experiences with them.

So far so good! I have written two posts which have been read by thousands of people and delivered hundreds of great questions. You can see the first two here:

Thanks for reading. If you would like to submit a questions please end it to me at


This Year’s Resolutions

After skipping on New Year’s Resolutions last year, I think it’s time to go back to what worked: writing them down and making them public. Two years ago I made these 3 resolutions. I stuck to two of them, and cooking / eating healthy ended up becoming a habit.

To keep the same structure I am going to share my two resolutions as a 5-year vision and a 3-month plan.


Resolution 1:

5-Year Vision: Be able to answer questions about India

3-Month Plan: Learn something about Indian culture every week

My trip to India last March made it clear to me how little I knew about the country and my heritage. It’s embarrassing how many times I’ve been asked to confirm something about Indian culture, only to google the answer like everyone else. I have made it a goal to learn something new about Indian culture every week. To keep myself to task, a friend and I have started, a mailing list where we share a few facts about Indian culture each week. The mission is simple – help people to understand more about India and then expand to allow everyone to understand their heritage. If you are interested, please subscribe!


Resolution 2:

5-Year Vision: Be equally as likely to pick up a book as to turn on the TV

3-Month Plan: Read 25 pages a day

I have never been a book worm. Reading was always something that school forced me to do. Perhaps it was a combination of books I didn’t like and strict reading requirements, but reading became something to avoid. In high school, since I never expanded my vocabulary by reading, I actually had to memorize the definitions of thousands of words for the SAT.

This needs to change. Reading not only improves creative and critical thinking it is also one of the best ways to learn from the experiences of others. While it’s unlikely I’ll be the person that reads a book a week, I’d like to simply be in a place where reading a book is just as enjoyable as anything else. This will also help me plow through the books I have collected as gifts over the last couple years!


That’s it – I tried to keep it simple. Did you make a resolution this year? I’d love to help you think through a 3-month plan and a 5-year vision.

How the Military Scales a Technology Leader

First Round Capital recently shared advice from Adam Pisoni (co-founder of Yammer) about how to scale oneself as a technology leader. He gave five tips, including one he learned from General (Ret.) Stanley McChrystal. This made me wonder what the military solution equivalent would be for Adam’s other 4 suggestions. After a bit of research, here is what I discovered:

  1. Roles & Responsibilities

According to Adam, “Without clearly defined accountabilities, it’s easy for companies to become paralyzed by decision debt and arguments.” The military uses something called the “G-staff model” to help define roles and responsibilities. Each branch of the military uses this model to define one leader as responsible for each of the roles below:

G1 – Deputy Chief of Staff for Personnel, G2 – Deputy CoS for Intelligence, G3 – Deputy CoS for Operations, G4 – Deputy CoS for Logistics, etc.

From there, they have a team to support the execution and function. The U.S. Army Material Command does a good job of explaining it here.

  1. Monitoring Progress

Adam covered this one well by using lessons from General McChrystal. Adam credits McChrystal for “creating a process where every single day for 90 minutes, thousands of people from all over the world would dial in to a rapid-fire update meeting. Each group had 90 seconds to say what they did, what they’re doing next and what the risks or blockers are.” By holding a weekly standup, McChrystal was able to ensure that everyone possessed the appropriate amount of baseline information to execute missions quickly and effectively.

  1. Retrospectives

The major lesson here is that members of the tech industry should aim to “stop repeating mistakes.” The military uses After Action Reports (AARs) to evaluate the success or failure of missions and learn how to improve for the future. I tackled how the Navy uses AAR in a previous post about development, and Craig Mullaney does an excellent job explaining the AAR in more detail here.

  1. Planning and Prioritization

Adam outlines a strategy for how to best create plans, but I think the most interesting part is how he concludes: “based on your new priorities, decide what you’re going to STOP doing.” To accomplish this, the military uses the appropriately named Military Decision-Making Process (MDMP). The MDMP is a 7-step process that is explained in detail in this textbook, but essentially comes down to understanding the mission, developing appropriate Course of Actions (COAs), war gaming the COAs, and then executing.

  1. Managing Tension

As Adam points out, tension between employees is inevitable. Evidently, the military agrees. They have a position – the executive officer (XO) – who helps to resolve tension within a unit. Going into each new project/initiative, the XO will convene all relevant parties/stakeholders to identify issues, allocate decision-making space, and hash out solutions. Adam agrees with this process and says, “instead of digging in and trying to resolve tensions as a leader, your only goal should be to make tensions public.”



Three Military-Tested Techniques for Improving Your Team’s Decision-Making

This was originally published in Fast Company:

“Captain, to the bridge.”

Mike LeFever, captain of the USS Destroyer, was abruptly awoken to these words at 3 a.m. to learn that a newly appointed officer had nearly crashed a $100 million cruiser into a fishing boat. As LeFever approached the officer, he could see a bead of sweat running down the young man’s neck. First, LeFever asked a set of rapid-fire questions: “What happened? Is anybody hurt? Is the ship okay?”

The officer answered concisely but still braced for the worst. Instead, he heard, “What did you learn? Let’s talk about this in the morning. You have three more hours on watch duty.” Then LeFever returned to his quarters.


Unlike in many—or even most—organizations, the military is relentlessly focused on developing the decision-making abilities of its personnel through empowerment. “If you take care of the people,” LeFever, who retired as a vice admiral after a more than 30-year Navy career, told me when we spoke recently, “the people will take care of you and perform the mission.”


In this view, people—their skills, expertise, and judgment under pressure—are inseparably linked with the success or failure of every undertaking. LeFever defines empowerment as delegating responsibility, and then allowing people broad freedom of action—permitting them to succeed or fail.

LeFever could have decided to use the interaction with the young officer on the bridge to dress him down in front of his subordinates. But he recognized that that served little purpose. The incident had already occurred. What mattered now was to make sure that the officer learned from this experience so he could prevent it from happening again.

The idea of empowerment is challenging enough when failure means missing a product deadline, but handing off that kind of decision-making when failure could mean a loss of lives? That takes a different level of trust altogether. Yet the military faces many similar challenges that organizations do when it comes to investing that trust in individuals:

  • Constantly changing teams, as military units are continually created and disbanded
  • Geographic separation, with personnel on almost every continent and teams varying in size from two people to tens of thousands
  • Rigid promotion requirements and dismissal protocol

The military still manages to enable individual decision-making not despite these challenges, but in order to counteract their potentially detrimental effects. In other words, only by cultivating leaders at all levels is such a large, complex organization able to maintain its effectiveness at scale.

“The hardest part of being a leader,” LeFever says, “is allowing other people to do that job, because they probably won’t do it the way that you want it. My goal was to provide guidance and boundaries.”

The military’s rigid organizational systems are designed to create the boundaries that are most likely to enable decisive action, not prevent it. These are a few of them.


After every mission, the Navy conducts an “after action report.” The process is designed to determine what happened in a given incident and why. Officers across different continents scrutinize events, debate and defend decisions, and resolve conflicting understandings of the scenario in order to learn how better to approach similar ones in the future.


The Navy’s mentorship program epitomizes the organization’s way of creating empowerment through clearly defined working processes. Not only does the Navy assign formal mentors, it also encourages sailors to seek out informal mentors on their own. These mentors then set quantifiable milestones for young officers to work toward short- and long-term goals.

The concept of a formal mentor is foreign to most entrepreneurs—especially during startups’ early days. When a company has three people and a product nobody’s ever heard of, where would a formal mentor even come from? You have to seek them on your own. When my cofounder and I first began to target film studio partners for our startup ReelSurfer, neither of us had ever worked with one. So I cold-emailed everyone from our alma mater’s alumni list who had entertainment experience. From one of these emails we formed an amazing relationship with a Hollywood producer, who then helped us start conversations and negotiate deals we’d never have been able to do on our own.

Not only can a mentor help guide you in our own decision-making, giving you the confidence to take action in difficult circumstances, they can also help create the situations that allow you to exercise (and, over time, improve) your judgment in the first place.


How a team is put together also has an impact on how empowered its individual members can become to make tough calls effectively.

When LeFever first joined the Navy, its personnel strategy revolved around skill requirements, commonly referred to as “Fill.” Finding that strategy wanting, LeFever proposed a new policy, “Fit and Fill,” which combined skill requirements and team chemistry.


This is an area many entrepreneurs and business leaders struggle with when forming new teams. It isn’t always easy to balance cultural fit and expertise. Startup founders are often overzealous simply to hire the smartest people they know. But sometimes the most brilliant people clash with each other or scoff at doing some of the less glamorous work. Members of poorly composed teams might not hesitate to make decisions, but they’re more liable to do so independently, less effectively, and without enough regard for the team’s unifying goals.

Truthfully, before speaking with Captain LeFever, my understanding of leadership development in the military stretched about as far as the drill sergeant scene in Full Metal Jacket. I thought of the military as a rigidly hierarchal, top-down organization. We like to think of the tech world as the complete opposite. But in reality, it’s a focus on leadership development through empowerment at the lowest possible level that allows the military to operate at the scale and excellence that it does. That’s a lesson more businesses would do well to take to heart.

Constrained Storytelling


“Explain to me how photosynthesis works…

Great job. Now explain it to me in half the words…

Excellent. Now do it again.”

Call me Mr. Miyagi. After graduating from college, I tutored high school students. If you ask any of the students who I tutored, they would probably describe my style as “frustrating.” Any time they ever explained anything to me, I would challenge them to explain it to me again, only this time using half the words.

I had no prior teaching experience, but felt that if a student could explain a concept to me in a few words, then they would understand it well enough to succeed on a test. Lucky for me, it worked.

What I think the students didn’t realize is that this is still hard for me (though they probably did). They have no idea how long it took me to boil down the ReelSurfer or Napwell value proposition into one sentence.

Describing your company’s mission while you are still figuring out what your company does is a constant battle. To me this is “constrained storytelling,” and it is one of the most valuable skills you can learn.

My next and latest attempt to blog regularly and to further improve my constrained storytelling is by writing haikus for companies that explain their mission. I plan on sharing them on twitter (@njcar) and will add them to this post as I go.

To start, I tried this for McChrystal Group, a company founded by Gen (Ret.) Stanley McChrystal to improve adaptability in organizations:

An embrace of change,

Achieving a shared vision,

Every level leads.

If you have ideas for companies, please let me know!

Lessons Learned from a Shark Tank Survivor

I’ve given a lot of pitches – to investors, customers, friends, and to really anyone willing to listen. Some go well and others are complete disasters, but all give me the opportunity to make the next one better. Recently, I was given the opportunity to pitch our product, Napwell, on ABC’s Shark Tank.

To see the full segment including Q&A click here. We are in segment 3.

Shark Tank was never on our list of priorities. My co-founder and I were in the middle of our Kickstarter campaign, which achieved 130% of its goal, when we saw a tweet from the casting director. Being huge fans of the show, we had to give it a try.

While I have successfully raised money from investors and have even been on TV before, being in “The Tank” was so different. Sure, it’s like a normal investor pitch, only with millions of strangers watching you share your dreams (no big deal). Here are three lessons I learned that can hopefully help you start your company or survive a tough pitch.

  1. Set the stage

The show is structured to make the Tank intimidating. The Sharks are not only professionally impressive, but also very experienced at sparring with entrepreneurs and making compelling television.

When strategizing for the pitch, I recalled advice from my high school tennis coach: playing to your opponent’s strengths puts you at an immediate disadvantage. In other words, instead of being reactive, be bold and set the stage. The first iteration of our pitch was completely different from the one that aired – it was dry and filled with statistics to highlight our scientific backgrounds.

At the last minute, we scrapped our initial plan in favor of pajamas and sleep zombies. We thought our pajama look would force the Sharks to question our legitimacy and lead them to ask the questions we wanted to answer. We knew that our strength as a company is our academic backgrounds and entrepreneurial experiences. It was probably a shock to them that Justin is a PhD candidate and that I have already launched a few start-ups.

This lesson extends beyond the Tank. While pitching a product, the more you control the flow, the more confident and prepared you will be. Setting the stage is especially important when presenting to a group with as much experience as the Sharks.

  1. Always be selling (and closing)

Preach, Alec Baldwin, Preach.

While Shark Tank is an amazing and rare opportunity to pitch to a powerful group of investors, it is also a way to share your brand with millions of potential customers. Even if all the Sharks passed, we knew that there were future investors, partners, and customers watching at home.

While answering the Sharks’ questions, we tried to make sure that the audience understood the problem that our product solves. To make our message as clear as possible, we created a list of three talking points:

  1. We are experts in sleep science
  2. We have achieved lofty sales targets without spending a single dollar on marketing
  3. We are solving a problem that affects hundreds of millions of people

Entrepreneurship requires you to sell not only your product, but also yourself. Though the target may change, you will always be trying to convince investors, customers, and even employees to buy your vision of the future. I’ve yet to meet a successful entrepreneur who cannot do this to some degree. In order to close the deal, either work on developing this skill or partner with someone who can.

  1. When trying to win, you have to be willing to lose

If you haven’t seen the episode, <spoiler alert!> we did not receive funding from the Sharks. It’s okay: their objections were very reasonable. In fact, it was a risk for us to be on Shark Tank at all. Napwell is still in the very early stages. While some of the companies on the show already have millions in revenue, we are still improving the product and incorporating early customer feedback.

While we knew that a negative reaction from the Sharks could bruise our egos, we couldn’t turn down this learning opportunity. After all, a rejection from the Sharks is just the judgment of five people. If your goal is to make a significant impact, it’s naïve to think that there won’t be stumbling blocks along the way. The key is to not let it affect your confidence. Of course we wanted the Sharks’ support, but the show also needs high ratings, and they achieve that through interesting companies and founders like us. We took comfort in the fact that we deserved to be there.

Having worked with and befriended many incredible founders, I have noticed one constant: unwavering confidence. The best entrepreneurs are those that are willing to face impossible risks in order to win. If those risks turn into failures, they are resilient and adaptable. They turn them into lessons, instead of disasters.

That’s it. I’m happy to say that we survived the show and even enjoyed our experience. I hope you can use these lessons to improve your pitch, and I look forward to watching you in the Tank.