The Story of How a Business Guy Earned the Opportunity to Co-Found a Tech Startup

I recently heard the story of how my friend met his cofounder and had to share it. I think there are some great lessons here for business folks looking to team up with smart technical people. I changed the names and am vague about certain details because they don’t really need the attention from this story, but it’s all true.

Chris’s First Startup

I met Chris at Stanford: really smart guy who studied CS and has a great eye for design. He cofounded a company right out of college, a collaborative editing/viewing tool, raised a round of funding, grew the team to six and eventually sold it for a small sum to a much larger technology-for-enterprise firm.

Chris stayed on post-acquisition, working on various projects for his new employer. While heading up a mobile app project, he ran into an challenge and can’t find a good solution for it in the marketplace. He decided to start working on a home-baked solution on nights and weekends as it was somewhat tangential to his day job, but wisely kept his employer in the loop about his efforts*. The entrepreneurial side of him started to wonder if there might be more firms out there with the same problem.

Meeting the Business Guy

Chris began working on it as a nights and weekends project, letting his firm know he was making this for the company, but that he also saw greater potential for it. One day, at a tech meet up event, Chris strikes up a conversation with a guy named Mike. Mike is a few years older than Chris and has been a part of the tech scene for some time, having most notably hacked on a consumer web product that got strong traction in the early-to-mid 2000’s.

However, these days Mike spends his time blogging, advising startups and angel investing. He’s turned into a “business guy”. Mike is intrigued by Chris’s side project and tells him:

“That’s a great idea. But you gotta stop calling it a side project, because it’s clearly a startup idea. Listen, I’d like to be involved. I think I could really help you out.”

Chris rolls his eyes. Having sold his last company, he doesn’t really need money – there are lots of investor who want to back a successful entrepreneur with a new idea. What does Mike have to offer? He has been out of the game technically for a few years and his experience is in consumer web, not enterprise, which is what this new idea would be for.

“Sure, whatever,” Chris replies, “I’ll let you know if I take it further.”

Hustling Pays Off

Some time passes and Chris has nearly forgotten about the whole interaction. Then, out of the blue, he gets a phone call:

“Hey it’s Mike.”

Oh boy, now what?

“Listen, I was serious about helping out. Over the last two weeks, I’ve called over 40 companies and pitched your product. I’ve gotten 30 who are willing to integrate with your service and try it out.”

Whoa. Now we’re talking.

I’ll skip ahead.

After meeting up, talking quite a bit more and working together, Chris and Mike eventually decide to join forces and co-found a new startup together. They raised a seed round and then a series less than 6 months later, have gotten tons of press and most importantly, has been a hit in the mobile development industry, with 100’s of customers ranging from one-man dev shops to publicly traded companies.

Lessons Learned

It’s dangerous to extrapolate too much from a story, but every data point is worth something. Here are two take aways:

  • You gotta be legit. Mike was already an impressive guy, with money, connections, professional clout and a technical background. But being legit wasn’t enough.
  • You gotta overdeliver. Mike didn’t complain about how Chris didn’t “appreciate the value he brought to the table”. He went out and proved that he could bring in business for the company. Getting a hold of the right person at 40 companies in a few weeks and actually convincing ~30 of them to say yes on a cold call, without a demo or even screenshots, is very hard.

If you’re a non-technical guy looking to co-found a startup, realize that you have far less leverage than whoever you choose to work with for your technical co-founder. You have to prove your worth both from the resources you have access to, the skills you can bring to bear on the project, and your relentless resourcefulness for getting sh*t done.

Do you have a story about co-founders meeting that you’d like to share? Leave it in the comments!

Photo Credit – stuck in customs

FOOTNOTES

*the company, to their credit, was pretty open and happy about Chris’s side project efforts

If You Want Perspective, You’ve Got to Climb Mountains

Randy Pang Echo Peak

Randy Pang, my cofounder at Ridejoy, on the summit of Echo Peaks in Yosemite.

Having perspective is powerful.

When you ask for advice from a mentor or advisor, you are reaping the benefits of their perspective. They have a different (often higher) vantage point from which to see the situation and offer suggestions. But how do you get that perspective?

I recently ran two trail races that had a lot of uphill climbs. Trudging up those steep hills was no fun. We were sweating and grinding forward on a path that seemed to go up indefinitely.

When we finally reached the top, we were rewarded with incredible views of the surrounding area. You could see out for miles, across enormous swaths of of the Bay Area.

We got to enjoy this beautiful vantage point for most of the race and it was glorious.

It has occurred to me that to get great perspective, to get sound judgement and a better sense of what you ought to do in a given situation, you need to climb mountains.

These mountains can be literal, like the ones in my trail race, or metaphorical ones: dealing with tough challenges, making progress and pushing ahead:

  • Working on a startup
  • Raising a child
  • Launching a new product
  • Shooting a documentary
  • Recovering from an addiction
  • Traveling to foreign lands.

These things are hard, scary and sometimes dangerous. But it’s the struggle (and eventual success) that gives you wisdom.

A parent, a veteran entrepreneur, a seasoned traveler – these people have hard-earned perspective that came from their facing the steep hills of their lives and forging ahead. Sometimes they slipped back a little or had to stop and rest. But they always kept their eyes on the path, rallied and continued onward. Because that’s what it takes.

So remember:

If you want perspective, you’ve got to climb mountains.

 

Eleven Compelling Startup Pitch Archetypes (with examples from YC companies)

eleven compelling startup archetypes

Photo credit by TEDx Vancouver

Over the past few weeks, I’ve helped a handful of startups work on their YC applications and interviews. I spent much of the time brainstorming with the founders on the best way to explain their business in the most clear and compelling way possible. These founders knew a lot about the market and had spent months if not years developing their ideas, but that often meant they would be all over the place when talking about what they were doing. This caused their pitch to sound weak and not be as compelling as it could be.

Paul Graham is, among other things, really good at boiling companies down to their essence. When practicing for Demo Day, you’d see founders start to pitch their company and Paul would say “Wait, don’t say that. Why don’t you say you are doing ____” which summed up the company in a more beautiful and compelling way than anything the founder had previous pitched.

Startup Pitch Archetypes

When talking to an investor (or potential advisor, partner or other person who cares about the viability of your business success) you will talk at some point about all the major things: the market, the product, the team, the target customer, the business model etc — but how you lead the discussion and how you frame your points matters a lot.

From my experience at two demo days, talking to investors about Ridejoy and listening to lots of aspiring YC founders talk about their businesses, I realized that the best startup pitches seem to fall into several patterns. Depending on the type of business you’re building, who you’re pitching and your personal style, there are probably one or two archetypes that would be most compelling.

I’ve identified eleven compelling startup pitch archetypes (depending on how you slice it) and have tried to explain what they are, what they sound like, examples of YC companies that might have used this archetype and advice on how you might go about using it.

Take a look.

DISCLAIMER
– I tried to match YC companies to pitch archetypes that I thought made sense but I was not at their meetings with investors nor did I attempt to verify this article with them (not enough time). The “What it sounds like” quotes are all simply illustrations of what this type of pitch might sound like and are all written by me, not by other YC founders. I’m not trying to put words in anyone’s mouth. Finally, these pitches are not magic. Nothing works unless you do.

The Standard Pitch

What it is:

You’ve identified a problem / unmet need that a specific group of people have and have created product or service that addresses the need/solves the problem and is within your target customer’s budget.

What it sounds like:

“Over 40% of widget makers say they are “displeased” or “extremely displeased” with their widget designing software, particularly in areas X, Y and Z. We’ve built a better widget designer that is 2x as good in X, Y and Z than the competition” Continue reading…

13 Strategies to Get Buy-In for Your Great Ideas [art of buy-in 3/3]

13 strategies for buy in title image

Photo Credit by Highway Agency

This the final post in a 3 part series on the art of buy-in. Post 1 explained why some people almost always get their ideas shot down. Post 2 was a story about how I overcame the naysayers and got buy-in for my team dues idea . Post 3 outlines 13 specific strategies you can use to get your great ideas implemented.

——- 7 strategies I used in my effort to get a team dues implemented —–

1) Build a base of supporters

For a good idea to be adopted by a group, it’s not enough for most people to be on board – you need a few very vocal supporters to champion your idea. As captain, I had some positional authority, but I knew it would be important to enlist the support of former captains and friendly teammates before the presentation even happened. Taking the time to have one on one conversations to sell your idea to people you trust within the group is time consuming but vital to ensuring your pitch to the full group is successful.

2) Prepare to address objections

This seems obvious, but people generally don’t prep enough for objections. If you just dismiss people’s viewpoints, they don’t feel respected and will be more likely to fight your proposal. In this case, I knew there were at least three objections I had to address and I took time to appropriately address each one.

  • We don’t spend that much money as a team – I built out a very detailed spreadsheet with our team’s expenses which meant it was harder to challenge the amount I was requesting
  • I don’t have money on me – More of a timing thing, I waited until the guys had received their per diem
  • I don’t want to overpay – I promised my teammates we would stick to the budget and if that if there was money leftover it would be returned to them

3) Neutralize nay sayers

Even after addressing objections in a way that will please most people, there are often still nay sayers who just refuse to change, don’t want to do anything or perhaps dislike you personally. Making sure that Eric and Luke wouldn’t shut down my idea in front of the group was a key strategy for getting team dues through. Depending on your situation, there are a couple tactics you can take to neutralize naysayers:

  • Try to win them over in a one on one - Sometimes nay sayers just want attention.  Other times, they have a genuine concern or misunderstanding.  When you meet in person, you can create a safe environment to speak honestly, identify the underlying issue, and figure out what to do — without the pressure of egos or an audience.
  • Have someone they trust/respect win them over – you might have the right message for the naysayer but perhaps they need a different messenger. If you can convince someone they trust to make the case for idea (see building base of supporters) they might be able to get through when you couldn’t.
  • Use peer pressure to force them in line – if you have enough support, you can make them look like the bad guys – the ones holding everyone back from pursuing this great idea and thus pressure them into going with your proposal. This isn’t always easy to do and it could backfire.  Plus, I had a feeling Eric and Luke would just dig their heels in.
  • Cut them a deal – I used this technique when I offered to let Eric and Luke pay individually.  This can be a risky move, because if people find out about the special treatment, they may doubt my integrity and overall motives.  Why do some people get a deal but others don’t? Do you have to suck up to Jason or make a ruckus to be exempt from rules in the future?  In this case, it was worth taking a chance because I felt like most people would understand.
  • Strong arm them into agreeing – this is typically a last resort move – threatening to make their life miserable or eject them from the group (if you have that authority) are blunt objects that can work but will definitely cause some collateral damage and are best avoided.

4) Show them you have their best interests in mind

People need to know that you care about them and aren’t proposing an idea that really only benefits you. The best way to do this is to have a track record of generous contributions to the group (and to remind them of this track record).

In my case, I mention talking to Susan, who was an administrator in the athletic department and tried to get our team more money (by increasing the number of days of per diem we got from 4 to 6 or 7, which is what we usually got). I wasn’t successful but I mentioned it as a reminder of “Hey, remember, I’m out there busting my butt so we can get more money. Keep that in mind when you think about this.”

Find a way to show people you care about them and want what’s best for them – it will help them trust you when you suggest something new. Continue reading…

Out of My Element: Notes by a Former Gymnast-turned-Runner in His First Triathlon


photo credit: Manuls via photopin cc

I’m always evolving and experimenting with my writing style here. On this post, I tried to write in the style of a magazine article, like something out of the Atlantic or Esquire. Not too pretentious, but a bit more literary than my standard ass-kicking fare. Let me know what you think in the comments!

I’m standing in a crowd of people covered in spandex and neoprene.

As a former gymnast, this is nothing new. Seeing muscled adult males squeezed in tight, form-fitting material was once a commonplace occurrence for me. What is novel, however, is that instead of being in a heated, insulated gymnasium, I’m standing in front of a dock, overlooking a small harbor on a chilly morning in early spring.

I’m here to compete in my first sprint triathlon.

For a long time, my only knowledge of triathlons was the Ironman ― the grueling 140.6 mile race that is one of the greatest endurance challenges in the world. It’s a 2.4 mile swim followed by a 112 mile bike ride, followed by a marathon (26.2 miles). As the story goes, the competition combined several long standing distance races to settle a debate between several military officers about which sport ― cycling, swimming or running ― was the “greatest”. The first Ironman Triathlon was held in Hawaii in 1978 and has since grown considerably in both participation and renown.

I found out about more manageable triathlons for mere mortals after following a blogger named Joel Runyon, who writes about triathlons [1], adventure travel and doing impossible things. More personally, I’ve been in touch with a college friend – a former swimmer who, in a renewed focus on exercise and weight loss, found a passion for running and decided to compete in a sprint triathlon.

The buzzer goes off and away we go, paddling through the water. I am surprised and pleased by the ability of my rented wet suit to keep the chilly 55 degree harbor water at a distance. The wet suit does not, however, do anything to prevent the salty sea water from entering my mouth every time I take a breath. Even after a month of swim practice at the YMCA, I find myself struggling to keep a good stroke rhythm going.

Halfway through swim I begin to feel my arms lock up as the coldness starts to affect their ability to move. I try to push onward, hoping that I won’t have to cry out for one of the lifeguards mounted on kayaks to save me from drowning pathetically 20 feet from dry land.

“What was I thinking”, I ask myself “when I decided to sign up for this?”

Triathlons come in four flavors: Sprint, Olympic, Half-Ironman and Ironman, each featuring longer and longer distances. For beginners, a “sprint tri” is relatively doable – with swim distances of 400-800 meters, bike rides of 10-12 miles and run distances of 3 miles or perhaps a 5k. While I personally find the term “Sprint” a bit puzzling as the descriptor for this distance, I can definitely see how it is a faster paced race than any of the longer distances.

How I found myself participating in a sprint tri has been a bit of a surprise and mystery to my friends and family. How does a gymnast of 16 years, used to meets where total time on equipment over six events adds up to less than 10 min of actual exercise decide he wants to race in hour-plus long triathlons?

It all started with a life-long shame in my ability to run.

Running has always been one of my weaknesses. I distinctly remember struggling to run a mile in gym class in middle school one year (the 27 laps around our gym’s hardwood floor feeling like an eternity) and my father chiding me for “losing to girls” with an 11 minute something mile. I was able to write it during my years as a competitive a gymnast, since one’s ability to run a mile has little to do with one’s ability to do a two and a half twisting somersault.

About a decade after that middle school mile, I was lost in the psychological wasteland of a former collegiate athlete. Going to the gym and working out felt empty and pointless. It was then that I tried running again. The first “real” mile I ran after college took 11 minutes and 47 seconds, which translates to 5 MPH, a speed reserved for driving in parking lots.

I am finally catching my breath.

I made it out of the water unassisted (2nd to last of the men in my batch) and am now riding the commuter/road bike hybrid I was borrowing from my roommate along the first of three flat lollipop loops that was the bike course. It’s a joy to inhale fresh air without a mixture of salt and the constriction of a suit.

I have, however, entered a new realm of hazards because while the swim portion was relatively contained with just a dozen or so men in my age group in the water, the bike route has men and women of all categories, including the highly competitive collegiate athletes. Sweaty bikers whizz by in gleaming blurs of carbon fiber and aero bars with a distinct zoom that sound more automotive in nature than pedal-powered.

I actually have to pull over to the curb as one fierce biker shouts for me to get out of her away. Did she say “on your left” or “move to the left”? I’ll never know.

Jason holding bike triathlon

A post-race shot of me and my borrowed commuter/road bike hybrid

Undeterred by my slow first run, and fueled by the keen desire to challenge and redeem myself, I began to put more miles on the road. My passion came not just from a need to conquer this weakness of my athletic ability, but of my skelo-muscular abilities as well.

I dislocated my left knee in my junior year of college in a disastrous vaulting accident and have undergone over five reconstructive surgeries to rebuild or trim my ACL, PCL and surrounding ligaments and tissues. Yet somehow running, especially in minimal footwear with a forefoot strike, has not given my knee issues and even my surgeon ― after examining my knee in an annual checkup ― grudgingly allowed me to continue running.

I was determined to turn running into a strength. And in the proceeding months, I did just that ― increasing my speed and distances from 5ks to 10ks to half marathons.

But after training for and competing in my first half marathon, I found myself suffering overuse issues in my feet that were frustrating and kept me off the road. And so looking around Active.com ― a website that lists sporting events and various types of races in one’s local area ― I found a sprint triathlon nearby held by my own alma mater.

I decided to enroll in the “Stanford Treeathlon“.

After getting passed endlessly for miles, I finally settle into a good pace and even catch myself passing a few people. I rip into an energy gel and drink a few gulps of water while trading “leads” with a boy who couldn’t have been older than 15. He’s even gracious enough to give me a “Good Job!” when I passed him. What a sport.

I try to kick it up a notch and attempt to chase down a girl in a white tank top. While I do pass her once, she catches back up and leaves me in the dust. Pulling in after my third loop I’m a little winded and my quads a bit sore, but otherwise feeling pretty good. I’m excited for “my” part of the tri ― the run.

The bike route gives a great view onto the sidewalk where I see triathletes stumbling away with terrible form, more shuffle than stride. I am excited to knock this leg out of the park.

It turned out training for a triathlon wasn’t very easy. The running was straightforward, but I don’t own a nice road bike, nor did my normal gym have pool access. I found a nearby YMCA and squeezed into lanes alongside senior and adult swimmers just looking to get in their morning dip. I suspect the lifeguards had a good laugh as I splashed away like a maniac, panting and half drowning as I put in my laps.

After swimming I’d get one of the spinning bikes and go for 20 or 30 minutes. Of course while those bikes are better at mimicking a real road bike, they don’t give you any digital feedback on distance or difficulty so I wasn’t sure how close this was to race conditions or even how hard I could push myself on the bike. My one cycling foray on actual road was a 12 mile round-trip ride across San Francisco out to the ocean that, with hills and traffic lights, took nearly 45 minutes each way.

I realized I did not really know how the race would go or how much it would tax me.

I struggle a bit to put on my Vibrams Five Fingers (my minimal running shoes that resemble “foot gloves”), my toes uncooperative and unwilling to slide into their proper spots. Eventually they’re wrestle them into position and I’m off.

Really off.

Everything feels wrong. My legs feel like they’re made out of lead. Shock from each footstrike resonate directly into my chest cavity and my heart feels like the clapper inside a church bell. Suddenly I realize why so many of those runners looked awful ― because they felt awful. I urge myself onward, slowing down my pace a little while I try to get my legs under me.

They come back about a mile in. Finally, I feel like I’m in my element. Foot in front of foot ― I’m moving. It’s pure sport, uncluttered by the brand of my suit, or the material of my frame. I hold an 8 minute a mile pace until I can almost see the finish line, then throw in my final kick, flying through the blue rubber mats that cover the timing machinery.

My total time clocks in a 1:29:40, putting me 2nd to last in the 25-29 year old male age group, and 154 overall, in perhaps 200 something competitors. My splits are 16:08 mins on swim, 43:20 on the bike and 23:28 mins on the run with 3+ minute transition times.

Jason racing sprint triathlon

The final sprint home!

Overall, I am happy with the outcome of my first sprint tri. In retrospect, I think I could have pushed myself a little harder on both the bike and run, though I definitely maxed out my swim. Some smarter racing tactics could have further shaved a few minutes off my time ― for instance my transitions could have been much faster.

There was definitely something exhilarating about running into the transition area, shucking a wetsuit or helmet and switching into new equipment. It felt like a being a Transformer (the phrase “activate running mode” seems like a catch phrase that could go on an ironic triathlete t-shirt).

I can also see the advantages of racing tri’s ― more variety in training and more room for optimization in a variety of area. Beyond just swimming, cycling and running more, improvements can come from learning a skill or technique (for instance, I could really benefit from swimming lessons) and simply buying just better gear. It almost reminds me of those casual Facebook-connected games where you can either earn your currency from in-game activities, or shortcut to them by converting your real money.

I personally don’t find all these areas of optimization very appealing. One of the few ways that gymnastics is similar to running is that the equipment is relatively standardized. While your home gym may differ from other gyms, at the competition, you are all wearing the same kind of spandex, the same wrist supports, hand grips and other attire and none of it guarantees a significant improvement in performance.

Similarly, in a running race, all that really matters is that you’ve got a decent pair of running shoes. Races feel more level and running feels more primal. Distance running feels like the ultimate competition, especially if you believe the claims by Christopher McDougall in his best-selling book Born to Run [2].

I’ll probably race another tri someday. Maybe I’ll even do the Treeathlon again, next year. I’m proud to have completed my first race and have a new level of respect for those Ironmen. But for now I think I’m going to stick with running. I’ve got a full marathon coming up in July and perhaps some fun races in between.

For once, I’m shying away from the shiny new thing, and pushing farther down simple, (but not easy!) road. I’d like to believe I’m doing things the way a real runner would.


FOOTNOTES

[1] In fact, he actually recently wrote an entire guide on sprint triathlons that you can check out here. [2] In the book, McDougall argues that the ability to run long distances is one of the distinguishing features of modern human beings and may have lead to hunting advantages over Neanderthals.