I Can’t Sing

I can’t code. I can’t design. I can’t dance. I can’t get in shape. I can’t draw. I can’t give speeches. I can’t write. I can’t invent.


By Lestat (Jan Mehlich)

When I was 15 I had a friend named Patrick. We met in driver’s ed.

If you looked at him, you’d probably expect to find him in a mosh pit, or playing insanely loud punk music. You’d be right. But the guy had the voice of an angel and sang in his high school choir.

One night, Collin and I pick Patrick up from choir practice. Collin was our 16 year old friend who we often made drive us around. Poor Collin 🙂

As we were driving to who knows where (some cafe to play chess and drink coffee or to Taco Bell) a song came on the radio that I liked. And I sang it a little.

That weird looking, punk rock, 15 year old kid gave me some advice that has helped shape every single thing I’ve accomplished since.

He warned me that, as I sang, I was trying to imitate the musician on the radio, and I wasn’t doing a very good job of it. My voice just couldn’t do what we were listening to.

Instead, I should try to cover the same song but do it in a way that suited my voice. My voice isn’t very strong at those high notes. If I was going to imitate anyone, try to imitate someone’s voice that works at this low pitch.

I tried Patrick’s advice, and I sang the song at a considerably lower pitch that was comfortable to me. I remember it sounded now more like Johnny Cash. The result was surprising. It wasn’t half bad, and it was much better than me trying to sing like that guy on the radio.


I’ve never felt like a “web designer”. I’ve been building websites for 15 years, and I’ve done what I’ve needed to do, but I could never get my stuff to look even close to those beautiful creations I admire.

To get past that, I’d end up buying a template someone else made. Or finding really good business partners who could design all the things I couldn’t.

A handful of years ago, however, running my third software company, I found myself alone trying to create a new project.

I didn’t have a partner, or a designer or anyone else to help me. And I didn’t have any money to spend getting the help. A template wasn’t going to cut it this time. I was in a bind.

I don’t have a Dribbble account full of my work. I don’t have a portfolio. I don’t know what awards designers win. I hear there are awards.

But I had to figure out what I can design. I had to figure out a way to design that suits me.

Since I can’t do a lot with color, or illustrations, or shadows, or logos, I’d have to go with very little of those things. It would have to be the basics.

I still looked at people doing amazing work online for inspiration. But instead of trying to step into the shoes of my preconceived notion of a designer, I started noticing elements of projects that I could actually do myself.

I can’t create an identity or logo like Aaron Draplin, but I sure could use Futura Bold and add a little space between the letters like he seems to be doing.

I ended up with what you see at Draft, software I’ve made to help me write better.

It has no logo. It has zero images. There’s one color on the homepage. Blue.

Thank god or luck or hard work or whatever, I have stumbled on a large number of people that appreciate and love the user experience and user interface I’ve created. I’ve worked my ass off to accomplish this project. But I didn’t expect this.

Of course there’s plenty of blemishes that you might see (and even more that I do). Mountains of things I need to improve and polish. And I’ll never think it’s as good as anything from my heros who I immediately think of when someone says: designer.

But somehow, along the way of getting here, I have figured out a way to design. I found some way to sing this song but with a voice that suits me.

You might not be able to sing like your preconceived model of how a singer sings, but I’ll never understand when someone tells me, “I can’t sing.”

You probably didn’t have a friend like Patrick.


P.S. It would be awesome to meet you on Twitter, or see where this has all led to what I’m now doing with Highrise.

Tips for getting clients? Sell cake.


Hasterb asks on Reddit:

Hey Guys, We run a monthly subscription that provides a certain service for other businesses. At the moment we have a few clients but are currently really struggling to get some more. We have only really been in business for a couple of weeks but was hoping for some more clients. At the moment we have a tried a fair bit, mainly trying to build a twitter following and keeping our blog up to date at the moment (daily high quality posts) in order to build some authority. We have also sent out a heap of emails (tried a few different subjects + content) but still not really getting any more customers. So my question to /r/Entrepreneur is, what are some tips you have for getting clients in a service based industry?

Years ago a guy decided he had some talent making cakes and wanted to start a business. But he had no clue how to start. So he went to his dad who is already a successful entrepreneur and PhD in Economics and asked him how to get started. His Dad’s reply? “If you want to have a cake business, you need to sell cake.”

So this wannabe business owner took his father’s advice to heart. He went out and hustled cake. He built the best fake cake he could. Then he figured he needed to be where people naturally were going to become cake customers. Not in the yellow pages. Not on the internet. Not making cold calls. He went and physically hung out where his customers were going to be: wedding venues! Brides-to-be are constantly at wedding venues. Checking them out. Getting ideas. Making reservations. So he went over to the wedding venue by his house and dressed in his Chef whites with this fake cake of his. And he just walked. Slowly. Up and down the sidewalk. He’d lap around and around for 5 hours. Eventually a bride-to-be would stop by the wedding venue to make a reservation for their own ceremony, and they’d see this baker and his beautiful fake cake, and they’d ask for a card. In a couple months of this, he was making cakes for every wedding at that venue.

Today? You might know him as Duff Goldman, or as Ace of Cakes, a very popular show on the Food Network that followed some of Duff’s successful career. There’s a lot to take from Duff’s story.

1. Have a product worth showing off

You have to make good things. You can’t skip this step. You need to look at your product and see if it’s actually any good. Lots of people put out things they aren’t even proud of. Duff knew his stuff was good. People would see this fake cake and want it. You have to get honest with yourself. Would you buy the service you’re selling? A lot of folks are too scared to face this reality. Their product stinks. But then they don’t put in the practice to get any better.

2. Take your time

You’ve been in business for a couple weeks? “Tried to build some authority” with a blog in that time? Duff on the time it took to get his business in gear:

Within two months, I was making the cakes for every wedding at the place (Two and a half years later, I had my own shop. We did things a little differently, because if I were just to make the same cupcakes everybody else does, nobody would care. So we made huge cakes and cakes in strange shapes. Then came my own TV show, and business exploded.

Two and a half years to get his own bakery! For most people their own shop is something they expect to have… today. But the reality is: to be successful with your own shop you could use a big audience behind you. So he scoped down his dreams and worked out of his apartment until he had enough business.

You’ve been at it a couple weeks. That’s nothing. It took me years of writing to build any semblance of an audience who would consistently read my stuff on Twitter (@natekontny) or Medium. You’ve got to put in some serious time and work to make a blog pay off. It’s totally worth it. But it’s an investment. You can’t get discouraged after a couple weeks.

Success takes time. Give yourselves some goals, but get realistic about how long it’s going to take to become great. Basecamp the company (37signals at the time) was around for 4 years before they even had 4000 blog subscribers to Signal v. Noise. With that, they launched Basecamp the product, and it still took another year to support 4 meager salaries with their software products.

3. Go to where your customers are — physically if you have to

Duff didn’t just spray and pray on the emails. There’s lots of bakers. Lots of websites and yellow page ads. Brides planning weddings are inundated with noise. So he went out and actually pounded pavement where no one else was.

Inkling, was my first business of any success that I started with Y Combinator in 2005. Our first customers were the result of some emails we sent, but we were able to stand out. There wasn’t any other Prediction Markets tools out that were doing software as a service. We could email someone and had very unique things to say about who we were. Is your service unique enough you can email someone about? If they aren’t, you’ll need to figure out how to stand out.

Go pound some actual pavement. Go get some meetings with people close to you. Don’t sell them anything, but set up some time with them to get some feedback on what you’re selling. A common email I would send out starting Inkling and later another business I did (Cityposh with Y Combinator in 2011), was just “Can I buy you coffee?” as the subject line. And I would just layer on the compliments about how much I liked their business and see if they had a moment to give me feedback on my latest project.

If the meeting had to be virtual I’d send “Can I buy you a virtual cup of coffee” and would send them a gift card to Starbucks if they accepted. This worked really well.

I remember sitting across from the owner of a bar in my neighborhood. He didn’t have a need for the product I was selling, but in that conversation he outlined exactly what he had a need for that he would buy from me. That conversation was great feedback to help me mold who I was trying to help, and if I had given up on that idea, this guy had just given me the next thing to work on and he would have been my first customer.

Go get those feedback meetings. Often they turn into their own deals. If someone you talk to thinks you’ve got something great on your hands, just end the feedback meeting with “So is this something we can explore using at your company?”

4. Make a fake cake!

One of our first clients at Inkling was O’Reilly Media. We did for free. Why? Because their logo and name was enough to get us a lot of free attention amongst even more potential clients. We did another deal with ABC San Francisco. They paid us a fraction of what we normally charged. Now they were getting our name on radio and television. One of our biggest deals was with Cisco and that’s because the guy who brought us in there had seen someone on ABC San Francisco talking about us.

These deals were like the fake cake. They weren’t the real high paying deals we wanted, but go find one or two high profile customers that you can leverage for more attention. And figure out how you can help them for nothing. If you have a useful product, you should be able to get at least one person with some clout that would love to have your service for nothing. I wouldn’t do this more than once or twice, but if you find the right one, that freebie is worth a ton.

5. What other fake cakes can you make?

What else can you do to show off your value. Open source everything. Put out lesson after lesson you’ve learned in your life. Share all the ways you’ve gotten these first customers. Share the things that are working and the things that aren’t. Go answer questions on forums where your “brides and grooms” are asking questions. Just like a couple going to a wedding venue, your customers are going somewhere to ask questions and get help. Go answer them. Reddit? Forums? They’re searching for answers to something. Be there to help. The more you do this, the more chances you have to drop links back to your own blog, Twitter account, business, etc.

6. Make crazy cakes

We did things a little differently, because if I were just to make the same cupcakes everybody else does, nobody would care. So we made huge cakes and cakes in strange shapes.

We can’t just keep doing what everyone else is doing. Today I’m the CEO of Highrise, web-based CRM software. When Highrise first came out in 2006, it was unlike a lot of things. It was simple unlike Salesforce. And it was software as a service unlike all the local databases and address books people were using to manage their contacts.

But today, Highrise was recently spun-off from Basecamp to get the love it deserves, and the market is really different. There’s a ton of CRM competitors. Good ones too. We can’t just do whatever everyone else is doing. So I do everything in my power to be different. I send feature announcement newsletters to our customers with pictures of my family to stand out from the soulless news everyone else is sending. I write and teach what you can learn from the inventor of Instant Ramen noodles vs. the content marketing garbage everywhere. We built a way to send simple text based bulk email vs. the trendy, graphic laden, slick email campaigns other vendors are trying to steer everyone to make. And on and on, we realize no one would care unless we offered something others weren’t.

Is your service different enough from everyone else? If it isn’t then I’d spend a ton of time figuring out how you can get it there. Two really important books that have helped me make products that are different and innovative enough to stand out from the competition are Blue Ocean Strategy and Something Really New. Spend a ton of time thinking about how you’re going to be different.


I hope this helps some of the folks looking for ways to reach their first or even their thousandth customer. If I can be of any help to anyone please let me know on Twitter or shoot me a brief email (nate.kontny on Gmail).

And to see how we’re living our own advice, you should follow what we’re doing at Highrise.

Poor design — “doesn’t say tea”

Reddit user earthtokeebs posted a design he had worked on for his client, Natural Warrior Tea.

http://imgur.com/a/JIbwP

Some of the reaction:

It’s very pretty but nothing about this package says ‘tea’ to me

Exactly. Cool tea products usually have that “zen” vibe. Not “let’s go rock climbing”.

Definitely. This doesn’t say “tea” at all. Reminds me of a company that tried to take on the wine market.


There’s so much wine. And wine has always had a culture. There’s historically been a typical way to design a wine. How it tastes. How you talk about it. The history you share on the bottle. How many varieties you have. Even how white and red is supposed to come in different shaped bottles. And wine has become something that you need to educate yourself about to be able to pick something when you visit a store.

But a company comes in and decides, screw it, let’s not make wine for wine drinkers. Let’s make it for people who buy things like ready-made cocktails and beer. People who are in and out of a liquor store and know nothing about wine. So they made only two kinds of wine: a single red and a single white. They used the same bottle design for both. They made them a bit fruitier and less complex in taste which made them more easy to drink by people used to drinking cocktails and beer. It got rid of all the junk about the history of the vineyard and typical stuff on the bottle — going with a simple logo of a Kangaroo.

Critics hated it. “Too sweet.” “Won’t make wine drinkers happy.” But that was the point. This isn’t for wine drinkers. The result: [yellow tail] in just 2 years become the fastest growing wine, and then quickly reached the number one wine in the US.


I agree. This design doesn’t say “tea”, but that’s really the strength of this. Tea is a ridiculous commodity. There’s already a lot of what you think about when you think fancy, “cool”, “zen” tea products. Why not make the tea for rock climbers? Why not focus on the people who want energy and caffeine from tea, but don’t really care for all the flavors and culture that the rest of the tea market caters to.

This [yellow tail] story is just one of a bunch of awesome case studies in: Blue Ocean Strategy. Anyone making products and business should give that book a thorough read. Our goal should be to find market space that is uncontested. A blue ocean. If you try and compete with everyone else you end up in these bloody red oceans competing on things like price alone.

P.S. To see how we ourselves are taking on the bloody space of CRM and finding uncontested waters since we spun-off from Basecamp, you should follow what we’re doing at Highrise and the story on Twitter: here.

How I managed to get Tim Ferriss to advise me, launch a product to a huge audience, and take over…


You probably have no idea who Jason Allred is. Most people don’t. He’s a 35-year-old pro golfer who is far from a household name. Golf’s tough, and Jason has had more downs than ups with the game.

“At the end of 2008, Allred had lost his PGA Tour card, then failed to regain it in the qualifying tournament, leaving him nowhere to play in 2009.”

–Mike Tokito

Then he got to play in the 2010 U.S. Open. That was over five years ago. After that? Not another tour event, until all of a sudden he had a couple good tournaments in 2014. Great, right?

Not exactly. A couple good random tournaments doesn’t really mean much for a PGA golfer’s career. Even good, pro players can’t just play in any PGA tournament. If anyone were allowed to try and qualify, the first day of a golf tournament would never end. So only a pretty elite group are invited to most tournaments.

But, there’s a loophole.

These tournaments are sponsored by big companies: Northwestern Mutual World Challenge, Hyundai Tournament of Champions, Sony Open, etc. And with big sponsorships, comes a say in who gets to play.

So, Jason, who wants a lot more from his PGA career, emailed the corporate sponsors of an upcoming tournament, the Memorial. But a bunch of players send these exemption request emails.

Jason took it up a notch.

He also sent pictures of his home life to let sponsors know that he’s not just a golfer, but a real person supporting a family. And he’s persistent. He followed up with another note — this time, handwritten.

Who handwrites anything anymore?

That got their attention.

“He wrote a nice, compelling, personal letter to the exemption committee. And that stuck with them.”

Dan Sullivan, the tournament director

The Saturday before the tournament, Dan Sullivan called Jason and offered him a spot.

Jason took full advantage of the opportunity — placing 15th. Not too shabby. It’s a six figure paycheck and chances for more tour play, all because he stuck his neck out a little more than anyone else to ask for help from people who had the power to.


In high school, I really wanted to play basketball. I tried out for the freshman team. I wasn’t good enough and was cut during tryouts. But my father encouraged me to find the coach at school and ask if I could help the team practice. My father figured they might just need warm bodies to play against, and through the experience, maybe I’d get better enough to make the team someday.

It was nerve-racking. I knew the office where the coach would be at lunch. But I couldn’t get myself to open the door.

I looped around the building a couple times, passing the door each time. I was too afraid to go in. But, knowing I couldn’t go home and tell my Dad I failed to accomplish this, I grabbed the door knob of the office with my sweat-soaked hand, opened it up and walked up to the coach and made my pitch, “I’d love an opportunity to help the team practice if you need anyone?” He smiled, thanked me for coming in.

Then he said, “No.”

Many people would take that as a setback and never try anything like it again.

But I learned a different lesson.

I felt this tremendous accomplishment walking out of that office. I wasn’t going to play basketball, but I just got up the courage to ask someone to help me in a way no one else was asking.

And nothing bad happened. I was a little embarrassed, but I didn’t die from being uncomfortable.

I could ask anyone anything.

Later in high school, I ended up on the volleyball team. Unlike basketball, I was pretty good compared to most of my peers. But by junior year, I hadn’t grown as strong as some of my teammates, so it was getting tougher to stand out from the crowd in ability.

I found myself getting stuck in what they call a “back row specialist” position. This is a good place for a player who is quick and good at defense. There’s nothing to be ashamed of. I was actually really good at it. But I wanted more. I didn’t want to get substituted out every time it was time for me to play offense.

So, I walked up to my coach after a practice and asked him, “How can I get good enough that you’d let me play offense?”

This had the exact effect I wanted.

During practice he’d work me hard in offensive drills and scrimmages. Eventually I got better. By the end of the season, I was one of his starting offensive players.


I’ve been really fortunate on where Draft (a software product I’ve made to help people write better) has gone. But it’s not strictly because of talent or luck. Like Jason Allred, I was initially able to put a few good things and ideas together, but I needed help to keep the project going.

My blog, Ninjas and Robots, has been instrumental in spreading Draft. I got a big audience boost because it was one of the first blogs on Dustin Curtis’ SVBTLE blog network. But it was “invite only”. How was I lucky enough to get one of those invites?

For awhile, I had a guy helping me with Draft. We would meet every now and then about Draft’s product design and strategy. He was the one that pushed for great ideas like “comment out” your writing and little details that have really caught people’s attention. That guy is Jason Fried, the well known entrepreneur behind Basecamp and the publication where you are reading this. And that all eventually led to Jason asking me to take over Highrise and turn it into its own business.

A lot of people keep asking me, “How on earth did you manage to get Jason as a mentor?”

I’ve gotten some other really insightful advice during an hour-long phone call about Draft with Tim Ferriss, who’s famous for his Four Hour books. The phone call led to five action items that immediately improved the product. Not to mention, he’s even recently mentioned his love for Draft on his podcast. How’d I get someone as busy as Tim Ferriss to give me the time of day?

Dustin Curtis, Jason Fried, Tim Ferriss — none of these guys reached out to me saying, “Nate, what can I do to help you?” Why would they? They are inundated with their own lives.

The only way I entered into their orbits was by simply following my Dad’s advice from that time I wanted to make the basketball team:

Open up your mouth and ask.


P.S. It would be awesome to meet you on Twitter, or check out how you can improve your chances of asking for opportunities and following up using Highrise.

Business Failing? You Might Be Asking The Wrong Questions


Going around asking for “feedback” won’t get you anything useful. Here’s how to dig deeper and find real answers.

I did fine in Catholic school, up until 6th grade. I don’t know why Sister Freda hated me, but I think she was trying to teach me a lesson. And I did learn a lesson — just not the one she had in mind.

The turning point happened like this. During a reading comprehension exercise about becoming a veterinarian, Sister Freda asked me, “Name one challenge people have in becoming a vet.” I gave an answer. It was wrong. She told the entire class that this is what happens when students don’t pay attention. If I had done the work, she explained, I would have seen the section in the reading that held the correct answer. It was intended as a humiliating lesson.

At lunch, I showed Sister Freda the reading passage in my book. She apparently wanted me to regurgitate the challenges that students face when becoming vets. But I pointed out a later paragraph that contained my answer — that many vets struggle to run their own practices as business people.

“Ah, ok,” she said, and that was it. She saw that my answer wasn’t wrong — if anything, her question had been too vague.

At that moment, I realized that teachers are like everyone else — they make mistakes. And if I was going to be a great student, I couldn’t be so passive about my education.

Starting in 7th grade, I asked a ridiculous number of questions. My hand lived above my head. I forced myself to think of hypothetical or advanced questions beyond the realm of the text or the day’s lesson. People groaned when I was called on.

I remember a fellow student turning around when tests were handed back. He noticed that I had gotten the higher score. “How did you get a 100% when you’re always so confused and have to ask so many questions?”

Despite ridicule from my peers, I kept at it. My grades soared, and at the end of 8th grade I graduated second in my class. If only I had asked more questions, sooner.


Don’t Forget The Real Question

Someone emailed me recently with the subject: “A question about start-ups.” But the email didn’t contain a question mark or anything remotely looking like a question.

Often I get advice seeking emails ending with, “Do you have any feedback?”
 But that’s not a question; it’s a cop-out.

Similarly, I’ve attended meetings where entrepreneurs make presentations to experts expected to share helpful guidance. But often the presentation is, “Here’s my product, what do you think?”

Same problem. That’s not a real question. And so a conversation with these experts is unfocused and frustrates the entrepreneur because her real problems go untouched.

I’ve made the same mistake myself, but I’ve been lucky to learn a different way. The most valuable feedback session I ever had with a mentor came before I released Draft, a software product I made to help people write better. I was prepared. Instead of asking for feedback, I asked how this mentor and successful entrepreneur would design a specific feature in Draft or how would he communicate the business model I had planned? I got much more than feedback; I got answers.


How To Ask Better Questions

There are plenty of people who’d love to help you with your business; you just have to ask, but they don’t have time to waste helping you figure out what your actual problems are. Get the most out of a potential mentor by approaching them with specific questions you’ve already identified and they’ve probably answered for themselves. How would you:

  • Increase the conversion rate?
  • Set up pricing?
  • Design this feature so that it’s clear and easy to use?

And force yourself to go deeper with your questions.

Toyota’s engineering processes are famously effective. One reason is that employees are taught to ask why five times when trying to solve a problem.

  • Why is the battery dead?
  • Why is the alternator broken?
  • Why didn’t the customer get alerted to this before?

This process helps engineers identify and fix the root problem instead of just treating symptoms. The same practice can be applied to your startup venture.

Act like a Toyota engineer and ask why at least five times.

  • Why is my business not making enough money?
  • Why am I not measuring my conversion and attrition rates?
  • Why is attrition so high?
  • Why haven’t I surveyed anyone who has canceled?
  • Why haven’t I added feature X which most canceling users are asking for?

And most importantly… Don’t worry about looking silly with the number of questions you have; just ask more of them.


P.S. It would be awesome to meet you on Twitter, or check out how we can help you start or improve your own business with Highrise.