Startup Purgatory

A friend once advised me to be careful of startup purgatory. The story below was my response to him.

Imagine two people setting out to cross a large lake, each in a small rowboat. The first sets out on a clear day with the lake surface as still and flat as a mirror; a gentle breeze and a steady current pushing the boat from behind. Each time the oars are dipped into the water the boat shoots across the lake. Rowing is easy and delightful. Quickly the rower reaches the far side of the lake. She may congratulate herself for being quite skilled.

The second rower heads out across the same lake during a great storm. Powerful winds, currents, and waves move in the direction opposite the boat. With each pull of the oars, the boat barely moves forward, only to lose most of the distance gained when the oars are raised out of the water for the next pull. After much effort she makes it to the far side of the lake. This rower may feel discouraged at her lack of skill.

Probably most people would prefer to be the first rower. However, the second rower is the one who has become stronger from the exertion and is thereby better prepared for future challenges.

From The Issue At Hand by Gil Fronsdale.


Last Sunday I raced the Wolfpack Hustle Marathon Crash, a bike race that follows the Los Angeles Marathon course hours before its start. It winds through the famous streets of LA while they’re dark and empty — Sunset Boulevard, Rodeo Drive, Wilshire Boulevard, Santa Monica Boulevard, and Hollywood Boulevard. Thousands of cyclists participated in what was an unreal experience and exciting bike race.

The morning started at 2:40am. Ryan and I woke up, put our kits on, applied chamois butter, filled our water bottles, and loaded our bikes in my truck. We were staying at my parents’ house in Palos Verdes, which is roughly an hour drive from the race start in Silverlake. My mom graciously offered to give us a ride, and we departed at 3:00am. We got to the race at 4:00am and were greeted by thousands of cyclists completely congesting Sunset Boulevard.


The scene was like nothing I’ve seen — blinking lights everywhere, music, and lots and lots of bikes. It felt like Critical Mass, but much, much larger. Like Critical Mass, the crowd was very diverse. People were on fixies, in kits, on time trial bikes, in jeans, on road bikes, in costumes, and sometimes on beach cruisers, too. Although the majority of participants were hipsters on fixies, some without brakes or helmets.

We stumbled through the crowd looking for our friends — Lukas and Brian, and Brian’s two friends Jon and Brett. We found them in time for the 4:30am race start.

“Race” is perhaps a bad description. Of all the cyclists lined up on Sunset Boulevard, the front of the group was composed of people intending to race. However, the back of the group was composed of people joy riding. Our original plan was to joy ride, but about five miles into the ride we started racing. It was too hard not too. We were riding down huge, open, famous streets, completely empty of cars and full of other cyclists we just couldn’t resist contesting.

At first the six of us stayed together, sometimes getting separated slightly by the ebb and flow of the disorganized pack. But at the second climb, about three miles in, Brian and Jon attacked and Ryan, Lukas and I didn’t chase — we weren’t “racing” yet. As Brian and Jon attacked, they passed a guy on a fixed gear walking his bike up the hill. As Brian passed him at 20mph, he turned to him and yelled, “THERE’S NO WALKING IN BICYCLE RACING!”

Each of the first two climbs fragmented the pack — faster riders got ahead of the slower riders. We climbed relatively quickly, so by the time we were over both hills, we were mostly among racers. And whether we knew it or not at the time, we were about to blow them up — cycling speak for go faster than them.

Lukas, Ryan and I got organized and started sharing pulls. For non-cyclists, “sharing pulls” means taking turns riding at the front, which is much more work than riding behind someone else. Before we realized it, we were averaging 24mph and passing everyone.

We got to a descent with a tight right turn at the bottom. As we made the turn, we noticed two riders had been in a crash. Then we noticed one of them was Jon. As we passed we considered stopping, but from the sidewalk I heard Brian yell, “Keep going!” We kept going.

We passed dudes on fixed gears. We passed girls on beach cruisers. We passed other kitted racers on fancy road bikes with big, dished, carbon wheels. I was only concentrating on two things: “BEAST MODE” and “Uhhhh, can I maintain this?” Numerous times, either after a pull or while trying to keep up with Ryan or Lukas, I thought I was at my limit, that I wouldn’t be able to maintain our pace. But we kept pushing each other, and we kept the pace fast. And we kept accelerating.

We were never passed by someone who we didn’t immediately catch up to. For example, one dude on a road bike wearing a high-vis jacket (newb) passed us twice. Each time we caught him moments later, after he hit his limit and couldn’t stay ahead of us. The second time he passed us, I screamed to Lukas, who was at the front, “GET ON THAT WHEEL, LUKAS!” I was pissed the guy had the nerve to try and pass us again!

At one point, eight or ten riders were riding behind Ryan, Lukas, and me. But they weren’t sharing pulls. The three of us were rotating in and out, and the rest of the pack was behind us, holding on for dear life. I considered turning around, staring at them, and yelling, “YOU GUYS EVER GONNA TAKE A PULL?!” But I decided against it — I figured it was better to keep quiet than yell at people. Plus, they’d probably slow us down if they got in the front.

On a flat, smooth road, we passed another peloton of about 15 riders. But we didn’t just pass them. We FLEW by them. I was on the front as we passed them. I had my elbows on my handlebars in a very aero posture, with my head down staring at my handlebars. I didn’t look at them as we blew by. All I thought was, “LATER MOTHA FUCKAS!!!!” We were flying.

With about three miles to go, we turned onto San Vicente Boulevard, a beautifully smooth, wide, dark road. About 20 riders had formed a peloton behind us, and the competition started heating up. Ryan, Lukas and I were still at the front of the peloton, rotating in and out, and speeding up. We were averaging 29mph, our headlights leading a path through the darkness..

When Ryan was in the front, a guy in a kit on a fixed gear passed us and got in front of Ryan. Almost immediately the guy hit a cadence he couldn’t maintain and started slowing down. At which point we were passed by eight or ten guys. UGH. Why did that dude on a fixed gear pass a bunch of geared riders hammering at 29mph?!?!

I knew we were nearing the sprint, so I sprinted up alongside the eight or ten guys who passed us, where I found a gap and entered it. I was the third wheel and in perfect position for the sprint. We turned the final corner onto Ocean Boulevard, and I sprinted up to 37.7mph and won the field sprint for our little group.

At the end of the race, Lukas, Ryan and I regrouped, shared a bunch of high fives and hugs, and reminisced about how EPIC the ride was. We were so stoked! We were never passed by anyone who stayed ahead of us. We did all the passing. We had pushed each other far out of our comfort zone and were stoked at the pace we were able to maintain for the 28 mile race.

Eventually Brian, Jon, and Brett found us. Jon shared his story about his crash. As he descended at 30mph and approached the tight right turn, a guy on a fixed gear with no brakes was trying desperately to slow himself down. He was moving all over the road and hit Jon just as they both entered the turn. Fortunately Jon and his bike only had minor scratches and bruises — he was able to finish the ride.

After sharing more stories, more high fives, and snapping a few photos, we decided we needed coffee and hot chocolate. We looked for a donut shop, couldn’t find one, and ended up at a 24-hour McDonald’s. We told more stories as we ate hash browns and sipped our warm drinks in the dark.

Rather than taking further advantage of my mom’s generosity, Ryan and I decided to ride along the beach from Santa Monica back to Palos Verdes. The 24-mile ride took us an hour and forty-five minutes. I was in survival mode the entire ride, struggling to turn my pedals over and keep up with Ryan.

We made it back to my parent’s house around 8:30am, four hours after the race had started, and nearly six hours after we woke up. We got out of our kits, showered, dressed, and drove to my favorite breakfast burrito spot, Phanny’s. We took the burritos back to my parents house, ate, then lied on the couch for a nap. Two and half hours later I woke up feeling great.

Ryan and I uploaded our rides to Strava and discovered that Lukas, Ryan, and I had the 31st, 32nd, and 33rd fastest times of the whole race. We averaged 22.5mph. We were STOKED. Those results are awesome, especially considering we weren’t racing for the first five miles, and when we were racing, we were only a group of three. Whereas the racers who started at the front probably had a larger group and hence could maintain a faster average mile-per-hour.

All in all, the ride was unbelievably awesome. We had tons of fun riding through the empty, dark streets of LA. But the best part of the ride was the camaraderie — we were pushing each other out of our comfort zones together, and were unbelievably proud to have hammered so hard.

I’m planning to do it again next year. And next time, I’ll start much further towards the front with the other racers. I should have known that I wouldn’t actually joy ride once my adrenaline kicked in :).


My Rafting Adventure at Joe’s Diner

The left side of our yellow raft is in the river and the right side is pointed towards the sky. All of my friends have been ejected from the raft and are swimming for their lives. And in a few moments I’ll be joining them. I’ll never forget this last image before our raft flipped in a rapid called Joe’s Diner.

At the time the accident happened, I didn’t think I was going to die, but then again maybe I should have been more worried. I can think of several defining moments in my life that have shaped me into who I am. The story I’ll share today is perhaps the most defining. It’s at least the most exciting.


In July 2005, six friends, my dad, brother, and I spent the weekend whitewater rafting in Kernville, CA, a small town on the Kern River 50 miles northeast of Bakersfield. Our confidence was high after several other successful trips, so we planned to challenge ourselves with difficult rapids. We didn’t think much about it — bigger rapids meant more fun!

We arrived at our campsite Thursday night with a plan to raft the following three days. Seven of us manned one raft — my brother, five very close friends, and me. My dad and another friend were each in their own kayak.

Rapids are classified according to their difficulty and danger. Classifications start at 2 and go up to 6, where a class 2 is a small, harmless rapid, and a class 6 is likely to kill you. Most guided recreational rafting trips do class 3 and 4 rapids.

We started off our trip on Friday by rafting the Lower Kern, an 11-mile stretch lasting all day. It’s a perfect first day, because it has easy, large rapids that are tons of fun and not too dangerous. Plus most of the stretch is whitewater, with only a few calm, lazy sections.

The last rapid of the Lower Kern is called Pinball, a difficult class 4 with lots of obstacles. Our previous trips down the Lower Kern always ended with a bad run through Pinball — we’d get stuck on rocks, bounced around, etc. This time we ran it flawlessly. This was a perfect end to the day, and a huge boost to our confidence.


I captained the raft from the rear, where I’d yell commands to maneuver us down the river. Each person in the raft had their own paddle. The commands I yelled were simple: an instruction to either paddle backwards or forwards. For example, I may have yelled “right forward,” signifying that the right side of the raft should paddle forward. “All back” meant that everyone should paddle backwards. And so on and so forth.

We started the second day with more confidence and a knack to challenge ourselves further. We ran several different sections, all consisting of difficult class 4 rapids. We were on fire all day — this was the best we had ever rafted. We wanted to go bigger before the day was over — we wanted to do a class 5.

For the last run of the day, we brought our raft down the hillside above a class 5 rapid called Bombs Away. The rapid is short, but it’s big. It has a 15ft drop followed by a huge wave. In all fairness, it’s relatively easy to run on a raft compared to a kayak. Nonetheless, we were scared and pumped up. Only six of us got in the raft — everyone else was too scared or too tired.

Normally when we approach a rapid, we hoot and holler with excitement, anticipating a fun and exciting ride. This time, we were silent except for my yell of “ALL FORWARD!” — a signal to paddle like hell. We entered the rapid perfectly, dropping for what seemed like forever. Jon, sitting at the front, noticed that all of a sudden he was paddling air — water was no longer below him. Finally we slammed into the huge wave waiting at the bottom. My dad, who was sitting at the rear with me, flew forward and hit my brother in the back of the head with his paddle. I was launched sideways into the well of the raft, where I was unable to see what was happening. After a few seconds I found my footing and got up to observe the damage. Pure chaos. No one was in their paddling position. Everyone had been pushed into the middle of the raft. My dad was making feeble attempts at paddling from his low, awkward position in the raft. His paddle was barely touching the water. Everyone else was stumbling to sit back up.

Eventually we all recovered, got into our positions, and screamed with excitement. Chaos is the source fun in whitewater, and we found plenty of it on Bombs Away. We finished the rapid, which after the drop was relatively calm. We had run Bombs Away flawlessly. Our confidence was at a new high. We slapped all our paddles together in celebration and exited the river to end the day.

We returned to our campsite that night with high spirits. We had finished two epic days of rafting. We ran several difficult class 4 rapids without problems. And we ran a big class 5 flawlessly. We could raft anything, or so we thought … until the next day.

We all woke up slowly Sunday morning, hazy from the evening celebration. We took our time preparing breakfast and lazed around the campsite. We decided to do one more run  before packing our bags and heading home. We picked a short run near our campsite, which just so happened to be our favorite stretch: the Limestone Run.

The Limestone Run has two large class 4 rapids: Limestone Rapid and Joe’s Diner, along with a few easy class 3 rapids. The whole run takes less than an hour. The day before we ran the Limestone Run two or three times. And we had rafted the Limestone Run several times before this trip, too.

My dad and two friends dropped the rest of us off with the raft at the start of the run. They were tired from the previous two days and decided to sit the final day out. After they dropped us off, they drove to the end of the run and waited for our arrival.

The six of us started by inflating the raft. The process took about 20 minutes and started on land. Once the raft was pumped up, we put it in the river and left it to sit for a few minutes. The cold water cools the air inside the raft, which causes it to contract, hence deflating the raft slightly. Once the raft was cool, we used the pump to inflate the raft further. A partially-inflated raft is sluggish and less maneuverable.

As we pushed off the rock to start our run, I noticed immediately that our raft still wasn’t fully inflated. The thought crossed my mind to stop and add more air, but I decided against it — we were good, and I knew it.

The first rapid was Limestone Rapid, an easy, big class 4. We stumbled our way through it, making sloppy mistakes here and there. We hadn’t fully woken up yet, and our sluggish raft wasn’t helping.

The next rapid was Joe’s Diner, also an easy, big class 4, with a large sweeping left turn and two large holes on the right side of the turn. A hole is an obstacle that recirculates water behind an underwater rock, as seen here. Holes can be dangerous for kayakers, but rafts typically go right through them. Furthermore, we often go through holes on purpose just for the wild ride. We had gone through both large holes on Joe’s Diner the day before, enjoying ourselves the whole time.

We entered the rapid correctly and started making our way around the left turn. I wanted to avoid the two large holes because I wanted our final day to go smoothly. I shouted “right forward” to turn the raft slightly left. Then “ALL FORWARD” to move us down the rapid and away from the holes. As we paddled we moved forward but not left — our raft wasn’t maneuvering as it had the day before. We were headed strait for the first large hole. And we were sideways. Once I knew we wouldn’t avoid the hole, I made a call for “RIGHT BACK, LEFT FORWARD” to quickly point the raft into the hole. The move was executed in time and we entered the hole strait.

All of a sudden we were sideways, our left side up river and our right side down river. We had entered the hole strait and left it moments later sideways. We were going strait for the second hole and we were still sideways. We didn’t have time to correct ourselves. A thought crossed my mind, “OH SHIT!”

We entered the second hole sideways and were immediately flipped, right side over left. Everyone was ejected from the raft instantly including me.

I struggled underwater for what seemed like an eternity. At first I saw nothing — the blackness of the river bottom. Then I saw white bubbles everywhere as I moved towards the surface with the help of my life vest. I surfaced and took a quick look around. Pure chaos. I saw my friends and brother swimming for their lives. I saw paddles, life vests, shoes, kicking hands and legs. And I saw the raft, upside down, racing downriver.

One thought popped into my head: I need to get to the raft. I knew this run eventually led into a fatal dam, and I knew the raft was our only way to get down and exit the river safely. I still had my paddle in my hand, so I threw it away and started swimming.

My view of the raft was constantly interrupted by waves and other holes. As I was swimming I was sucked underwater over and over again by waves and holes. I swam through debris — shirts and shoes — ignoring all of it. I needed to get to the raft.

I swam and swam and finally reached the raft. When I got to it, I found Jon (aka Zoo) holding on to one end. In one hand was the raft, in the other was two paddles. What a champion! I yelled to him with all my might, “ZOO, LET’S GET THIS FUCKER OVER!” He nodded. I grabbed the end of the raft with Zoo and we started kicking our way to the left side of the river.

We made slow progress, but eventually the raft was on the bank and we were standing on solid ground. I turned towards the river to see what others were doing. Dustin and Andrew had swam safely to the raft as well and were climbing onto the bank. My brother, who at the time was fourteen, and Nico were floating down river slowly making their way over. I yelled as loud as I could — as if it wasn’t already clear — to have them swim to the left side. With some struggle they eventually got over, but much below where I and the raft were. They hiked upriver to meet us. We were together again. And we were safe. No one was injured.

Although the six of us had survived, much of our gear hadn’t. Only one other person held onto their paddle, which meant we had three paddles plus a spare, totaling four paddles. Great. Six people, four paddles, a partially inflated raft, and several more class 3 rapids to get through. We rested a few moments, flipped the raft right-side up, and got ready for the rest of the run.

We bumped and stumbled our way through the class 3 rapids to the end of the run. My dad was waiting for us and was obviously worried. We had taken far longer than expected to get to the bottom. But we made it. We joked as college students do, “We all got sucked off at Joe’s Diner.” Very funny.

We all recounted the event and shared stories. Andrew, after being ejected from the raft, was held under for a few seconds and resurfaced under the raft. He dove under water trying to free himself, only to come up still under the raft. He did this several more times and eventually came up to daylight. Nico hit his head hard on a rock but was OK. Everyone else suffered the same journey as me: lots of turbulence, swimming, and episodes of being held underwater.

I was inspired to write this story after reading about the Tunnel Creek avalanche, an avalanche that claimed three lives in Washington. My friends, brother, and I are lucky that we’re alive to tell the tale of Joe’s Diner. Other adventure seekers aren’t always so lucky.

I’ve enjoyed adrenaline sports for as long as I can remember. My parents started me on skis when I was three. Today I enjoy mountain biking, road biking, snowboarding, snowmobiling, whitewater rafting, skateboarding, and surfing. These sports are dangerous. But my fondest memories are those similar to Joe’s Diner, where friends and I push our limits and find our edges. The risk is worth the excitement. I’ll continue with adrenaline sports for as long as my body lets me. I won’t let fear control me.

Since flipping our raft on Joe’s Diner, we’ve run the rapid successfully several times. We’re more careful, and we always inflate the raft fully.

group pic

Cycling Haleakala, Maui, Hawaii: 1 Climb, 10k Feet, 36 Miles

Screen Shot 2013-01-07 at 3.57.15 PM

On the day after New Years day, my Dad and I cycled up Haleakala, a dormant volcano in the Southeast of Maui, Hawaii.  The ride was 36 miles up and 36 miles down, starting at sea-level and peaking at 10,023 ft.  It’s the longest climb I’ve ever done by over 6,000 feet.

We rented bikes from the Maui Cyclery in Paia and picked them up that morning as soon as the store opened at 8am.  We were on the road by 9am and on our way up the volcano.


The ride is uphill the entire way save for one 100ft section that is slightly downhill.  There are literally no flat sections.  On the flip side, there’s only one brief section that’s over a 10% grade.  Otherwise the grade is consistently between 4% and 6%.

Prior to leaving we researched water stops along the route.  There’s a town 6.5 miles out, then another at 13 miles (elevation: ~3,000).  Then there’s a visitors center at around 26 miles (elevation: ~7,000).  The two towns had stores that sold water and food, but the visitors center only had water, no food.  We packed all our food, only stopping for water at 13 miles and 26 miles.

IMG_1149The weather and temperature were perfect.  At sea level the temperature was in the high 70s.  At the top the temperature was in the low 50s.  We were shielded from the sun by a high layer of clouds, which was great considering we needed to ride several hours between water stops.  The bike shop employees warned us of two things: that we might run out of water, and that we’d be very, very cold on the way down.  We were lucky to have the high clouds to hide us from a dehydrating sun, and to have relatively moderate temperatures.  We rode through dense fog from 4,000 feet to 7,000 feet but fortunately we had prepared the right clothing and didn’t get very wet.

The ride was brutally difficult.  We climbed for 5.5 hours at a gradual pace, taking rests when we needed them and stopping for water twice.  I kept saying to myself, “Only X thousand more feet to go!”  Then, “Damn that’s a lot of feet.”  But we kept going and made it all the way to the summit.  The descent took about 75 minutes.

My dad said it was the most epic thing he’s ever cycled.  It was probably the third most epic thing I’ve ever cycled, third behind the Devil Mountain Double and Death Ride respectively.  But epic nonetheless.  I’d totally do it again, and I’d totally recommend others ride it, too.  The trick is to pack enough food and warm clothes.  Otherwise, climb, climb, climb!

Get more stats about the ride on Strava.


The Boat and Two Arrows

Imagine yourself lying in a small rowboat on a calm lake, enjoying the gentle rocking of waves.  When all of a sudden another boat bumps into your boat, startling you with a loud bang and a sudden jolt.  Initially you’re angry — someone else deliberately bumped into your boat and interrupted your quiet moment.  What an ass!  However, when you sit up and look at the boat, you notice it’s empty.  The wind and current you were enjoying a moment ago pushed this other boat into yours.  Yet now you’ve lost concentration and your tranquility along with it.

Your discomfort is a result of two metaphorical arrows being shot at you.  The first arrow was the initial surprise and shock of another boat running into you.  The wind and current shot this arrow at you.  However, the second arrow was the anger that took away your calm state of mind.  You shot the second arrow at yourself.

The first arrow could not be avoided — you cannot control the other boat.  However, the second arrow could have been avoided.  If you were not so quick to assign blame and hence become angry, you could have continued to enjoy your serenity even after the initial disruption.

I expect this hypothetical story sounds familiar.  We commonly invent scenarios in our heads before we know all the facts.  We make assumptions about other people and we let those assumptions anger us, which creates a false distance between us and others.

Compassion breaks down assumptions about people, and hence lessens anger and its control over our mood.  Through practicing compassion we can avoid shooting ourselves with a second arrow.  Without shooting a second arrow we’ll be nicer to both friends and strangers, and we’ll be happier, too.  Try not to shoot the second arrow.

Story credit: here and here.  Photo credit: here.

A Little Inspiration Goes a Long Way

The following inspirational speech was given to the San Francisco Giants when they were nearly eliminated in the semi-finals leading up to the 2012 World Series.  The speech was given by Hunter Pence, an outfielder who had joined the team earlier in the year.

“Get in here, everyone get in here. Look into each other’s eyes, now! Look into each other’s eyes. I want one more day with you. It’s the most fun, the best team I have ever been on and no matter what happens, we must not give in. We owe it to each other; play for each other. I need one more day with you guys. I need to see what Theriot will wear tomorrow. I want to play defense behind Vogelsong because he’s never been to the playoffs. Play for each other, not yourself. Win each moment, win each inning. It’s all we have left.”

The Giants went on to win three games in a row to win the semi-finals.  Then they swept the Detroit Lions to win the World Series.  Sometimes a little inspiration goes a long way.

Source: here.

Do NOT Rush into a Founding Team

Most companies get founded when one entrepreneur has an idea that she recruits her friends to build with her.  The common assumption is each founder will work well together because they get along and their skills compliment one and other.  So the founding team gets formed right away, ownership and voting rights are set during the incorporation, and everyone starts working.

The scenario I’ve just explained often leads to one or many founders leaving the company.  They recognize after weeks or months of work that the company isn’t the right fit — maybe the role isn’t interesting, or maybe one of the other founders is too difficult to work with.  A company that loses one or many founders isn’t necessarily doomed for failure, but the process you’ll go through is messy, expensive, and emotionally draining for everyone.

The founding team should be formed carefully and patiently.  By being careful, you’ll save yourself much frustration in the future when one or many founders need to leave.

Here are the steps you should take when choosing a founding team:

  1. Get to know one and other — break bread and drink beer.
  2. Work on a side project — something that won’t share intellectual property with your future startup, yet something you’re passionate about.
  3. Brainstorm — bounce ideas off one and other; make sure you can rev on ideas.
  4. Push a few buttons — see what people do when they’re upset, sad, or vulnerable.
  5. Discuss the startup — the product, go-to-market strategy, branding, competitors.
  6. Discuss roles and responsibilities — who will run product, engineering, sales, recruiting, etc.
  7. Discuss the board and ownership — equity split, vesting schedule, and board seats.
  8. Incorporate and start working full-time, guns blazing.

Here are qualities you should look for in a founder:

  • They have a passion for the product.
  • They’re product minded.
  • They’re onboard for the long haul.
  • They have a skill that will give your startup a competitive advantage.
  • They’re fun to work with.
  • They’re good at communicating.
  • They’re positive, inspiring, and excited.
  • Ideally you’ve worked with them before.
  • They make you better at your job.

Here are founder qualities that should raise a red flag:

  • They’ve never worked at a startup before.
  • They have lots of side projects that they enjoy maintaining.
  • They’re considering going (back) to school or a job.
  • They want a quick exit (acquisition).
  • They’re hesitant to quit their preexisting commitments.
  • They don’t have a passion for the product.
  • They’re negative.

Lastly, here are general tips for incorporating.  These are very subjective:

  • Put everyone on the same vesting schedule — don’t forward-vest anyone. [1]
  • Give all founders a one-year vesting cliff. [1]
  • The founding CEO should be the founder most dedicated to the company’s success.
  • The founding CEO should have control, which usually means they have more stock.  (I used to think otherwise.  And there are lots of varying opinions on this subject.)

Don’t expect founding a company to happen quickly.  You should date potential founders for months before you decide to work together.  The founding team is more important than the idea — the founding team is everything.  Be careful and patient when choosing or joining a founding team.  And do not rush into a founding team.

[1] Each founder will work on the company for years, so vesting schedules don’t matter.

Update: Steve Blank agrees.

11 Tips for Finding an Apartment in San Francisco

Few “first-world problems” are more miserable than finding a place to live in San Francisco during a summer when the tech industry is booming and people are flocking to the city.  Each good rental listing will have 30+ interested parties bombarding the landlord or rental agency for private showings.  At open houses — many of which have more than 20 potential tenant attendees — visitors desperately compete for the attention of the renting party, trying to prove that they have all the qualities a qualified tenant should have.  Not to mention rent prices are out of control right now — average studios are renting for $1,800+.  I spent the last two months looking for an apartment in San Francisco.  I’m relieved to announce that I found an apartment I love last week and moved in this weekend.  And I’m sharing my advice with you in this blog post.

Before I dive into advice, I should provide some facts about my search:

  • Me and two male friends — Jon and Ryan — were looking for a three bedroom.
  • We were picky about our neighborhood — Mission, Lower Haight, Upper Haight, Cole Valley, NOPA, Western Addition, Divis, Hayes Valley,  Noe Valley, Inner Sunset, Inner Richmond, Castro.
  • And we weren’t willing to pay exorbitant rent prices to expedite our search.
  • Prior to moving, Jon and I lived together in a two bedroom, and Ryan lived in a different two bedroom.

And now onto my tips:

1: Check Craigslist very often

You need to know when a new listing becomes available, and you need to email or call the renting party to express your excitement as early as possible.  Find a good way to check Craigslist repeatedly throughout the day — I averaged about once an hour.  I built a Craigslist search tool to help me (developers: here’s the source).  Find a process that works well for you and stick to it.  There are plenty of qualified tentants looking at the same Craigslist listings, so you don’t have room to be lazy.

In our experience other listing websites weren’t as useful as Craigslist.

2: Be personable and professional

When you email or call the renting party, be kind, excited, and professional. Don’t waste their time with long phone calls or emails. Get down to business and save them time — you’ll be one of many qualified tenants, and they’ll be grateful for your conciseness.

3: Open houses for market research; private showings for applications

Open houses are awful for tenants interested in applying. They’re incredibly uncomfortable, because everyone is competing for the renting party’s attention. It’s like a pony show — “look at me, look at me! I’m great! Rent your place to me because I’m great!” The chances are very low that you’ll get a place through an open house. However, open houses are great for market research and application practice, which are both very important. Try to schedule a private showing for places you want to apply. And try to be the first applying party — there’s huge value in being first.  When asking for a private showing, tell the renting party that you want a private showing because you want them to have a chance to get to know you.

In summary, use open houses for research. Schedule private showings to apply.

4: Start early

Most places in San Francisco are available immediately — very few are available weeks or months in advance. You should still start looking at least one month ahead of your desired move-in date. You may get lucky and find a place that is available at the right time. And you’ll also get practice at your pitch and the application process in general.

5: Be prepared with application material

Go to every open house and showing with material about each potential tenant.  But only apply to places you like. For each tenant have the following information printed and organized into a Manila folder:

  • One general cover letter, with a photo and short bio of each tenant.
  • Generic application with basic information: social security number, previous landlords, personal references, employers, desired move-in date, etc. I’d suggest finding a generic application online.
  • Proof of income: pay stubs, bank statements, stock certificates, W2s, 1099s, anything to prove that you can afford rent.
  • Credit check and score from all three major credit reporting companies.

6: Offer more money if you can

A landlord will love the idea of getting more money for their unit. If you can afford to offer more than the list price, do it. They’ll appreciate your urgency.

7: Negotiating usually doesn’t work

Most places have too many qualified tenants applying — you almost certainly won’t have the upper hand in a negotiation.  That said, if a renting party likes you, you may be able to ask them to accomodate your needs.  For example, they may be open to slightly lower rent in exchange for tenants they have high confidence in.  But again, in general, negotiating won’t work in this market — it’s far too competitive.

8: Do whatever you can to make the renting party’s life easier

Finding an apartment sucks, and renting an apartment sucks, too.  Imagine trying to rent your own unit — the bombardment of incoming requests, stupid questions, disorganized, impatient, and stressed tenants.  Be sympathetic and do what you can to make the renting party’s life easier.  They’ll like you for it and consider you over other possibly more qualified applications.

9: Try to be first

There is no rule that says the first application will get the apartment. But being first makes a big difference. The renting party will remember you better, and if their first impression of you is good, they’ll probably rent to you. Show up to an open house early. Call new listings immediately and try to schedule private showings as soon as possible.

10: Make sacrifices

You’re going to have a hard time balancing work, your personal life, and your apartment hunt.  You’ll need to make the tough decision to set priorities.  The more you prioritize your apartment search, the faster it will be over.

11: Be patient and persistent

We found a place we loved after two months of searching. Most people I’ve spoken to who moved recently have given me the same feedback — finding a good place takes time, persistence, and patience. Don’t give up no matter how discouraged you get. Hang in there, and keep going. You’ll get lucky eventually, and until you do you need to come off as excited and friendly.

Bonus #12: Get Lucky

See Robert’s comment below.

Good luck to those of you looking right now.  It’s a brutal market out there.  But there’s hope.  Luck favors the kind and hard working.

Bonus #13: Understand Biases

Read this great blog post on apartment hunting biases.

One Year, Six Products: 16 Tips for New Entrepreneurs

Exactly one year ago I quit my job with the dream of starting a technology company.  I didn’t have a plan except to work hard and learn.  Yet I could have used a lot of advice in the early days, which is why I’m writing to you today.  My hope is that the below advice will help guide some of you if and when you make the decision to quit your job and pursue a startup.

I have two blog posts summarizing the year and the six products I’ve built.  The first — here — is a telling of what I’ve done, what products I’ve built and what I’ve learned from each.  The second — the post you’re reading right now — is a summary of advice for others who are in a similar position as I was a year ago.

1) Be prepared for dark days: the last year has been both the hardest and most amazing year of my life.  There have been days where I was angry at everyone, scared that my life-long dream would drift away out of reach because of my insufficiencies.  And there have been days when I’ve been on top of the world, literally running down the streets skipping with utter joy.  You’ll have both of these days, but you’ll remember the dark ones.  They’ll leave a stain on you that only washes off with a good attitude and a happy candor.

2) Try not to freak out about your personal runway: I have a panic attack once every few weeks about my personal finances.  I’ve emptied multiple 401k plans, consulted on the side, and sold other financial holdings that shouldn’t have been sold.  I’ve done what I’ve needed to do to survive, but I’ve probably done a little too much.  That is, I’ve let my anxiety control my financial decisions.

Set aside plenty of money to keep yourself afloat, and try not to stress out too much.  Chances are good you can find money to keep going when you’re close to running out.  But when you have money in the bank, try to focus on building your startup.  Easier said than done, at least for me :).

3) Raising money is not success: until recently I assumed that success meant raising money.  Perhaps the Silicon Valley culture has rubbed off on me too much.  Raising money is not success.  In fact, it’s an incredible distraction from running your business.  The lure of getting meetings with big-shot investors is strong, but your time is probably better spent elsewhere.

Only raise money if you truly need it.  Come up with a rough 6-12 month plan for your startup and determine all the possible costs.  If those costs are too large and can’t be offset with revenue or personal funds, raise money.  Otherwise, don’t raise money.  It’s as simple as that.  Furthermore, the best time to raise money is when you aren’t raising money.  Build your business/product, not your pitch.

Plenty of awesome businesses started without investment, Atlassian and Github to name two.  Raising money is not success unless you truly need the money.

4) Raising money is not easy: a common assumption right now is that raising money is easy because there’s a lot of it out there.  If you have an easy time raising money it’s either because you’re awesome or because you have shitty investors.  Good investors will ask great questions and find holes in your business.  You’ll need to do a lot of selling and a lot of convincing.  And you’ll need to infect them with your energy and passion for success.

If/when you decide to fundraise, take it seriously.  Learn from every meeting, find mentors to help you with your pitch and strategy, and go into meetings prepared.  Don’t let a bad meeting get you down.  You’ll probably have more bad meetings than good ones.

5) Start fundraising with investors who know you well: a successful seed round starts with one good investor.  With one good investor all other meetings you’ll have will be easy.  When it’s time to raise money, find someone who knows your market well and has worked with you in the past — your former CEO, a friend who’s in the space, etc.  Get this first investor to commit $10-50k on terms you both agree on.  Then go pitch other investors.  Pitching an investor when money is already committed is much easier than otherwise.  The conversation goes from “please give us money” to “you can participate if you want.”  The latter is a far better position to be in.

Again, try to get $50k committed from investors who know you before you speak to a professional investor.  If you’re interested in learning more about raising a seed round, I’d suggest you read this.

6) Customer development is key: customer development is the most important thing to get right in the early days.  The best customer development is with a product, not a survey.  Get a prototype out there, get people using it, and become friends with those people.  Your early adopters will make a huge impact on the success of your company.  Get to know them, treat them well, and listen.  They’ll fall in love and they’ll tell all their friends.

The following three questions matter the most:

  1. Why do you use our service?
  2. Will you continue to use our service?
  3. Will you pay $XYZ for our service?

Know the answers to these questions before you take any idea seriously.

When determining what features to build and what directions to go, never start with “I think we should …”  Always start with “Customers want X so we should …”  What you think doesn’t matter — your intuition is probably wrong, unless you’re incredibly talented or you’re your own customer.  Your customers are all that matters.  Without them you have nothing.

7) Team matters, a lot: there are incredibly few people out there who can build a successful startup by themselves.  Furthermore, finding good co-founders isn’t easy.  Pick a great team before you enter anything risky — before you pay legal fees for incorporating, before you plan to pursue something for the long term.

Pick team members who you’ve worked with before.  Have a total of 2-3 cofounders, anything more is too complicated.  Do not assume your team will work out until it does.  Doing a startup with someone else is like having a child or getting married.  You’re entering a commitment and everyone needs to have the same expectations around success, failure, and day-to-day operations.  Everyone needs to feel like a part of the team.  Otherwise your team will fail to work well together.  And your startup will probably fail, too.

Everyone on your team should have complimentary roles.  You shouldn’t overlap too much in what you want your role to be.  For example, two of three co-founders shouldn’t want to be the CEO or CTO.  This is an early sign of a dysfunctional team.

8) Divide equity evenly amongst the founders: I can’t stress this enough.  Do not be a founder with someone if the equity isn’t split evenly.  Uneven splits almost never make sense.  You’re all going to be busting your asses for years on this crazy idea of yours.  One person doesn’t deserve more — I don’t care how much more work they’ve done to get things started.  Split things evenly.  No exceptions.  The success of the company rests on each of your shoulders equally.  Compensate yourselves equally, too.

If one of your founders isn’t comfortable with an even split, they probably don’t trust the rest of the founding team, which isn’t good.  Or maybe they feel entitled, which also isn’t good.

If one founder did more upfront work than the other founders, put them on an accelerated vesting schedule.  Don’t give them more equity.

9) “Business people” fight an uphill battle: I don’t mean to discourage you, but your path to success is harder and longer than those who can build a product on their own.  Try to find a technical co-founder.  Unfortunately that’s the best advice I can give you.

10) Seek out advice and mentorship: make friends who are also entrepreneurs.  Find good advisors/mentors and meet with them regularly.  Try to work around other startups, either by camping at a friend’s office, or by paying for coworking space.

11) Balance passion, skill, and opportunityyou will succeed if you do something you love, something you’re good at, and something that has opportunity.  Try to build a startup that has a little of each of these.

12) Keep learning: you’ll never know all the answers.  After you read this post you’ll know more about the early startup process.  But when you finally get there you’ll have endless other things to learn.  Be ready for this.  Try to love the opportunity of learning something new.  Keep reading, and stay hungry for knowledge.

13) You might need to search a while for the right startup: I spent most of a year soul searching, building products and staying busy.  It took me nine months to find MemCachier, my current project that I’m in love with.  Don’t expect that after you quit your job you’ll know exactly what to build.  Stay busy, and ship as many products as you can while you’re in the experimentation phase.  You’ll find the right startup eventually.  And when you do, you’ll be so happy you spent time searching for it.

14) The best reason to get investment is for growth: investors want to invest in success.  Investing in a company without traction is risky.  Investing in a company that has traction and wants to see huge growth is less risky and very exciting.  There are plenty of good reasons to get investment.  But growth is the best reason.

15) Understand what type of investor you want: do you want an investor with good connections?  A trophy investor?  Someone with operational experience in your market?  Or do you just want money?  Understand what type of investor will help your business succeed and look for investors that fit the bill.

16) Starting a company is the most rewarding thing I’ve ever done: this whole process has been absolutely unbelievable.  There have been lots of hardships: my personal relationships have suffered, I’ve dried up nearly all of my financial holdings, my net income for the year is -$40,000, I hardly buy or indulge in anything, and I’ve been highly stressed for almost an entire year.  Yet I wouldn’t trade this last year for anything.  For the first time in my life I’ve found work that I love, which is truly difficult to do.  I’ve pursued my life long dream.  And I couldn’t be happier about it.  It’s all worth it.

Questions? I’m more than happy to answer them.  Write a comment and I’ll get to it soon.