I recently listened to a Masters of Scale podcast in which Airbnb founder Brian Chesky talked through the company’s tactics for growing past the first couple of dozen users. This is especially relevant now that LineupHero has gotten some traction in the rowing community, and we’re looking to move forward.

Beyond the famous story of Obama O’s and Cap’n McCain’s breakfast cereal lies a master class in design thinking. You can spend time worrying about a lot of things in the beginning — your branding, social media positioning, and overall marketing strategy, but in most cases that stuff doesn’t fucking matter. No, Chesky’s objective was to create unforgettable experiences with their product.

This isn’t a naive tale of how to make airbnb.com or RowHero “better,” or what features to add to app X on platform Y to get more engagement.

Instead, answer this question: what would it take to make the overall experience of your product so out-of-this-world that your customers have no choice but to tell everyone they know about it?

That’s a question I’d like to know the answer to for LineupHero.

Chesky applied this to Airbnb by envisioning pieces of the experience and grading them with a star rating. Not a crazy idea to most of us. Take check-in for example. You could imagine 1- and 2-star experiences start with your host not even being there to unlock the door or greet you. In a 5-star world the host greets you on time, helps you with your luggage, and shows you your room. OK, pretty standard — you’re not going to tell anyone about that.

But what if we could do more than that?

If time, money, and manpower weren’t constraints, what would a 6-, 7-, or even 8-star experience look like?

Brian Chesky: A six star experience: You knock on the door, the host opens. “Hey, I’m Reid. Welcome to my house.” You’re the host in this case. You would show them around. On the table would be a welcome gift. It would be a bottle of wine, maybe some candy. You’d open the fridge. There’s water. You go to the bathroom, there’s toiletries. The whole thing is great. That’s a six star experience. You’d say, “Wow I love this more than a hotel. I’m definitely going to use Airbnb again. It worked. Better than I expected.” What’s a seven star experience? You knock on the door. Reid Hoffman opens. Get in. “Welcome. Here’s my full kitchen. I know you like surfing. There’s a surfboard waiting for you. I’ve booked lessons for you. It’s going to be an amazing experience. By the way here’s my car. You can use my car. And I also want to surprise you. There’s this best restaurant in the city of San Francisco. I got you a table there.” And you’re like, “Whoa. This is way beyond.”

So what would a ten star check in be? A ten star check in would be The Beatles check in. In 1964. I’d get off the plane and there’d be 5,000 high school kids cheering my name with cars welcoming me to the country. I’d get to the front yard of your house and there’d be a press conference for me, and it would be just a mindfuck experience. So what would 11 star experience be? I would show up at the airport and you’d be there with Elon Musk and you’re saying, “You’re going to space.” The point of the the process is that maybe 9, 10, 11 are not feasible. But if you go through the crazy exercise of keep going, there’s some sweet spot between they showed up and they opened the door and I went to space. That’s the sweet spot. You have to almost design the extreme to come backwards.

Clearly there’s some transcendent customer experience going on here.

Before I take this whizzbang theory and apply it to LineupHero, I want to point out that in the example above, Chesky applied this to a single piece of the overall experience. You must still choose where that experience starts and ends. Often the customer’s problem does that for you.

Case in point: LineupHero is an app that saves you hours by helping plan your race lineups for a particular regatta. It finds the right place to put all your priority lineups in the schedule and then finds additional lineups to give all your athletes as many races as you want them to have.

But there’s more to a regatta than just the lineups, even for just a single team:

  • Deciding to go to a regatta
  • Determining which rowers can attend
  • Gathering desired lineups from the rowers
  • Brainstorming priority lineups as a coach
  • Creating lineups for everyone to have enough races
  • Selecting equipment for each lineup
  • Publishing lineups for your team to see
  • Entering the regatta with those lineups
  • Paying entry fees
  • Ensuring lineups are run in practice
  • Making hotel reservations
  • Merging heat sheets with lineups to know when every rower races
  • Communicating load, unload, and practice times to the team
  • Designating a space to transport each boat (trailer or car top)
  • Loading equipment
  • Driving to the venue
  • Keeping track of what needs to be done when on race day (rigging, derigging, launching, landing, watching, recording…)
  • Loading the trailer when races complete and boats are no longer used
  • Driving home
  • Unloading and rerigging boats

Even this list is mostly the basics, but let’s stop here. I’m going to cheat and apply the 11-star experience to the entire list. Even though we could certainly do this for each step in the list, let’s take the challenge of reimagining what a coach or team of coaches really has to do to plan a regatta.

1-star experience

by Xavier Sotomayor on Unsplash

You just barely managed to make entries before the regatta deadline. Rowers will race between 1 and 4 times because some events are already full, but you’re just happy you got everyone at least 1. Equipment isn’t assigned ahead of time but you’re sure you brought enough…but now that you think about it did those extra 4x riggers make it onto the trailer? Nope…no they did not.

You tried to communicate with all the rowers over email about rigging time but trying to copy and paste what seems like 10 thousand email addresses on your phone gives you constant anxiety that not everyone is reading your email and no one will show up. Turns out your dreams materialized because the next morning you arrive at the venue to supervise rigging and realize that the message you thought you sent out is still in your drafts folder.

Rowers trickle in as the coaches’ and coxswains’ meeting starts, and you manage to snag a printed schedule. Unfortunately, you’re at a regatta where the schedule runs late but even so, a few of the events you entered end up being moved earlier so you missed them. Changes are only announced over the loudspeaker, which nobody on your team can hear because your staging area is somehow across the street from the rest of the regatta.

Throughout the day you continuously miss being proactive launching and catching crews — even though you have a schedule, you tend to zone out talking to the rowers or other coaches. Thankfully rowers ask for your help to launch so you don’t completely miss everything.

At the end of the day, you tie down the remaining boats in slings and realize you never made a hotel reservation before the second day of the regatta. You sit morosely in the truck seriously contemplating sleeping in the trailer bed before summoning enough energy to find a budget motel 50 miles from the race course. As you put your head down you realize that day 2 of hell is yet to come.

OK that was pretty bad. I sincerely hope nobody has ever had an experience like this. Let’s build on it from here.

2-star experience

Congratulations, you showed up at the venue a little earlier so you got a good spot to launch from, and you managed to find a hotel ahead of time close to the race course. Even though you are now in range of the loudspeaker to hear changes in schedule, it’s a loudspeaker and you’re outside. You’re not going to hear anything. You still miss races. You still can’t seem to get a handle on when to launch and catch crews.

3-star experience

You assigned boats and oars ahead of time so it was clear what needed to be on the trailer, and no equipment was left at the boathouse.

You found a way to communicate better with all your rowers so they were all up to speed with rigging times. Everyone who needed to show up before the coxswain meeting did.

4-star experience

You had more time to prepare and gave everyone 3–4 races instead of just 1, even though you still have battle-scars from the multi-colored spreadsheet you planned it all in.

With your prep time you also looked at the heat sheets ahead of time and prepared exactly when you needed to launch and catch crews.

5-star experience

Your diligence in checking the heat sheets time and time again allowed you to catch the fact that some races were moved up. This time you didn’t miss anything, and the rowers had a great experience too.

Pretty standard stuff, so far, right? Notice as we went from the 1-star to 5-star experience, we added more work for the coach to do. More work that no doubt led to a better overall experience for everyone (including the rowers), but let’s fast forward to the 11-star experience to see what we can really achieve when we unshackle ourselves from constraints we normally face.

11-star experience

by Senor Sosa on Unsplash

2 weeks before entries open for the regatta an automated system reminds the entire team to declare their intention to go or not to go in addition to any specific lineups they’d like to row. 1 week later, that same system uses a combination of fast practice lineups, rowers’ preferences, and custom-generated lineups to give people no more than 3 races per day and no more than 4 total, based on how the club entered the regatta in previous years.

This system presents these lineups to you to make any final changes, including vetoing any lineups the system chose or creating additional lineups. As you make lineups, boats and oars are assigned automatically based on previous practice lineups and rower’s weights for your approval. You make a few changes after some consideration and then finalize your lineups.

Several things happen instantly:

  • Your lineups are staged for entry in RegattaCentral immediately when entries open.
  • All race lineups are published for the team.
  • Your practice lineups are set until the regatta so you can practice each race lineup multiple times.

While you supervise the lineups, the system makes hotel reservations for the team and arranges for catering from a favorite restaurant at the regatta venue for your team.

As soon as the regatta organizers post heat sheets, you and your team are notified with a new schedule that shows the times that every rower races on each day. As a coach, you receive a special itinerary that shows when to launch, land, and watch each crew race. Rowers receive special itineraries that just highlight their races. Furthermore, if either you or your rowers are interested in anyone else or any other crew, they can sign up for alerts whenever that athlete or crew races so they never miss cheering someone on.

As the regatta organizers finalize the schedule and make adjustments, your schedules are automatically updated so no one misses a race.

The system knows about your trailer and has already determined where to put each boat.

The national team happens to be taking a training break in your area and spends their time loading your trailer — they strap every boat, load every oar, and double check every piece of equipment is loaded and ready to go.

They follow you to the race and handle unloading, rigging, derigging, and loading throughout the regatta. They also hang out for the entire regatta and answer any question your team can throw at them.

Even though you’re deep in conversation, you are always notified when boats need to launch or are coming down the course so you don’t miss a chance to debrief with any racers.

Meanwhile, a professional camera crew with drones and launches decked out with camera equipment has set up along the course and captures every rower’s race with television-broadcast-like precision. This footage is available live as well as immediately after the race. Speed data has already been overlaid on top of the video feed using the data streams from SpeedCoaches. Video analysis has already pinpointed which technical improvements will lead to faster race results in future races with that lineup by the time they get off the water.

Of course, the national team is there to carry boats and oars from the water back to the staging area.

Not only can rowers see their finish times immediately but they can also compare those times against previous performances at other regattas. Since times aren’t always comparable, they can also compare how they did relative to the skill level of the athletes they competed against. (Interested? See chess ELO ratings.) This allows them to answer the question — did I actually improve relative to the caliber of my competition?

With this new information, you can sit down with your athletes and review video footage immediately after their races— to see where in the race they slowed down, and whether it was mostly due to fitness, technique, or both.

Throughout the regatta, athletes from every team can easily find other athletes looking for additional races in composite boats. You don’t worry when a rower approaches you for another race — the boat and oar usage is taken care of automatically for you so that there are no conflicts across the regatta.

Off the water, the rowers can see professional massage therapists for a tune-up for their next race, and the food available in the club tent provides optimal pre-race and post-race nutrition for every diet on your team.

At the end of a long day of racing, the crew enjoys each other’s company with a catered meal at the venue.


There’s a lot of technology in this anecdote, but the point is not the tech. All these services help rowers and coaches spend more time in the moment and less time worrying about their next move. And providing that environment — one to really build the coach-athlete relationship — is what really fosters the creation of unforgettable experiences.

Not everything in the 11-star experience is feasible, so what’s the minimum to take away to make it real? That’s when it starts to feel practical, possible, and magical. And apparently, as Brian Chesky alludes, a way to get people talking.

What’s in your 11-star experience?


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