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Ira Glass on killing your startup idea

I’ve been thinking a lot about Braintrust lately and whether this thing is truly going to fly or whether this is just a bad idea that I should kill.

There are a ton of different ways to think about it, some scientific (looking at customers, market, trajectory) and some more based on the gut (am I still excited by the idea and the space, does it look like I’m starting to build a tribe of followers, etc).

Interestingly enough, the greatest wisdom I came across on this subject came from an unconventional source. It was from this series of videos by one of my favorite journalists of all time, Ira Glass.

In the second part of this four part video where Ira talks about the art of storytelling, without even realizing it, he gives some amazing advice to entrepreneurs on how to think about their startup idea, how to curate it so it becomes something amazing, and also, of course, how to ruthlessly kill it if it doesn’t meet your expectations.

Here’s the video.

Categories: entrepreneurship.

An update on Tout, the web-app I built in 3-days

It’s been just about a month since I posted my article on how I built Tout and took it to market in 3 days. I think its time to do a bit of a retrospective and talk about how things are going.

To give the quick back story, I built Tout to “scratch my own itch.” I was sending out a ton of marketing and customer development emails for my other product Braintrust and I needed a way to do it more effectively. And so, I built Tout, a way to templatize my emails. Just for kicks, I added a Premium plan that would give web-site like analytics on the emails I sent.

The numbers

After about 30 days since launch, Tout has signed up a total of 334 users, processed about 1,600 pitches, and signed up 10 premium subscribers each paying $30 per month.

Changes to Tout over the first 30 days

Thanks to a rather passionate group of customers around Tout, I also received a ton of feedback around the service.

The first two weeks after launch were spent ironing out random bugs around the service, implementing things like a “Forgot Password” feature and adding some features that I wouldn’t have thought of myself such as integrating with Highrise, being able to change the greeting for templates for other languages, and ensuring people can put in HTML in their messages for customizations.

After the first two weeks or so, Tout got to a pretty humming state. It turns out the problem it was solving struck a real nerve in people. One of my customers put it best: “Copy-n-Paste is SO 1990s thanks to Tout.” With the fires put out, I started to focus more on customer development. I hooked up a Survey.io widget to gather feedback, and I also used Tout to email new users and ask them how their experience was going.

Screen Shot 2010 05 20 at 10.48.19 pm

About three weeks into the service being online, I got enough information from customers to realize that:

  1. people were looking for a slightly more polished interface for Tout (but admitted that it met their immediate need)

  2. and although some people were turned off by the $30 price tag, there were lots of people who were perfectly fine with it as long as I put in some certain features.

And so, on the three week mark, even with existing premium subscribers, I implemented the low hanging fruit of the premium features: the ability to share Tout Premium with up to 5 team members AND the ability to share the pitch templates across the team. This meant that if 5 of the team members used the same pitch template to deliver a consistent message, you’ll get 5x the amount of analytics data tracking whether your e-mail pitches (and messaging) is working with your audience.

The Premium update struck yet another nerve, followed with a set of emails saying “Perfect! I was waiting for exactly this feature…” I got yet another bump in revenues.

Over the last week or so, it seems I hit another peak, and people started to complain about slowness. And so, thanks to Heroku’s awesome infrastructure, I just dialed up the # of dynos, and added some background worker threads for synching Highrise and sending e-mails. Problem solved.

What’s next for Tout

Screen Shot 2010 04 29 at 10

At this point, I see a Premium subscriber sign up just about every other day or so. I told my self that since Braintrust is my first priority, working on Tout would not be worth it to me without the $30/month price tag. At this point, I’m pretty satisfied. Tout is more than paying for it self, and is also generating extra cash that I can feed into Braintrust.

More importantly, Tout is easily attracting the type of people that also happen to be perfect candidates for Braintrust. Which means that by placing a simple upsell link for Braintrust in Tout, I can more than recoup whatever time I’ve put into it already revenues aside.

Moving forward, I’ve got some killer feature ideas from my customers. As time permits, I’ll be implementing them over the next few weeks. If I see enough of a response from all of you, I’ll post another update reporting back in a few months or so.

Categories: my thoughts.

Introducing, Braintrust, my bootstrapped lean startup

I think an introduction to Braintrust in this blog is long overdue. While I’ve been writing a ton of blog entries about Tout (the web-app I built in 3 days), I wasn’t quite ready to officially introduce Braintrust up until now.

What is Braintrust?

First, let me explain the problem Braintrust tries to solve. I believe there is a magic spot between group e-mail collaboration and real-time chat. Historically, this has been filled by mailing lists and discussion forums, both of which now pale in comparison when it comes to the Web 2.0 user experience we demand from our tools.

Today, there are a handful of products trying to fill this void, trying to bridge the gap between e-mail and chat, keeping the organizational benefits of discussion forums, and introducing the snazziness of social networks, comments, and news feeds. Google Wave, SocialWok, and some others are examples of this space, and now, so is Braintrust. To be clear, Braintrust is not trying to be everything Google Wave is, it is simply trying to solve the same problem through my own vision of how the problem can be solved.

Simply put, Braintrust is a social collaboration tool that helps groups organize their conversations. I built Braintrust by combining the timeless elements of a traditional discussion forum and innovative features from popular social networks. Braintrust is hosted in the cloud, works in real-time, and provided as a SaaS offering.

For the impatient, here is a quick demo of how Braintrust works:

Why is Braintrust a lean startup?

First of all, up until a month or so ago, I never paid attention to the lean startup movement. After hearing/reading a lot about it, it just so turned out that my principles around starting a business by and large matched up to a lot of the practices that lean suggests. But, when looked at through the lens of lean, there are a lot of interesting observations.

When I started out with my idea for Braintrust, it wasn’t called Braintrust, and it didn’t look much like what Braintrust is today. As Steve Jobs said in his Stanford commencement speech, “you can’t connect the dots looking forward; you can only connect them looking backwards.” The Braintrust you see today is the result of atleast 3 major pivots (along with a number of smaller “recalibrations”) and a fair amount of customer development.

  1. My idea for Braintrust first started as a crowdsourcing tool where people could ask a question and have structured discussions (read: Q&A) on the best answer. I called it Recommnd. I pivoted away from this idea because a) UserVoice nailed it and b) I realized that I didn’t believe in crowdsourcing, I really just wanted to get the opinion of a select few that I trust.

  2. So my idea of Recommnd morphed into “Ask My Braintrust” — the idea was to take the interface I designed for crowdsourcing and apply it to a private set of “advisors” — a Braintrust if you will. While doing customer development around this product, I kept failing to reach “product market fit” — people loved the idea, but no one had a ready made group of advisors that they could tap into to create a Braintrust. And for the small number of people that did, the market just wasn’t big enough or wasn’t exciting enough. The best piece of advice I got during this phase was “You’re going after people and trying to convince them to create a group and then use your product… why not go after people that are already in a group?”

  3. And so, that lead to my third pivot. Instead of focusing on “advisors,” I focused on teams (a.k.a. existing groups). Also, instead of just trying to appeal to all kind of groups (e.g. families, social groups, communities), I decided to narrow my focus as well (this was one of the smaller re-calibrations).

  4. I don’t think I’m fully there yet, but I think I’ve reached a point with enough people loving the Braintrust product that I want to get it out to a larger audience. I wouldn’t be surprised if there are going to be a few more pivots in the path ahead, but I think the core product is by and large there.

The development of Braintrust has been lean as well. I did most of the development myself and used contractors when I could. With the size of Braintrust, and all of its moving pieces, it literally would have been impossible to build something like this without the use of open source and the common services on the cloud. So here goes the shoutouts:

  1. If it wasn’t obvious already, I’m a total Rails fanboy. Without Ruby on Rails, I don’t think I would be in the web business, and Braintrust almost certainly would not exist.

  2. Braintrust is hosted on EC2. Because it uses XMPP, ActiveMQ and ActiveMessaging to deliver the real-time features, going with Heroku like I did with Tout was not an option.

  3. Being a single founder, I didn’t want to risk wasting time on OPS, so I wanted to automate as much of my infrastructure configuration as possible. So I used Chef and Capistrano for infrastructure setup, packaging and deployments. Everything is automated. “chef-solo and cap production deploy” — you still rock my world.

  4. Not to boast or anything, but Braintrust has a ridiculously sick UI and User Experience. I mean it, but I can’t take credit for all of it. If it wasn’t for the AMAZING jQuery library and the even more amazing plugin development community, I’d never be able to get Braintrust to auto-expand text boxes, automatically embed Youtube videos using oEmbed, or show growl-like real-time notifications.

  5. I think special recognition also goes to the open-source community (and the magic of Github) in general, which lets not-so-talented developers like me bring my ideas to life. I really want to make it a goal to give back, I’m just afraid of whether the OS community is ready for my terrible coding skills. If I had to spend time writing G-Mail address book imports, or messaging libraries, Braintrust would never have come to market.

I think the last thing I want to mention is that lot of people think being lean means not having a vision. This wasn’t the case with Braintrust. Through customer development and pivoting, there were numerous times I could’ve slapped on a ToDo list to Braintrust and turned it into a project management tool and called it a day (otherwise known as Product-Market-Fit) — because that is what the people I was talking to were asking for. But, I stuck with my vision and my goal, that this would be a tool around conversation management and not about project management. I still don’t know for sure whether this was the right move, but helping people communicate better is what excites me, and so I stuck with that goal and to this day still continue to find a better product-market-fit. I have this vision, and I’m sticking to it.

So…what’s next?

Well, I’m still bootstrapped, but I’ve given my resignation at my day job to work on this full time. Whether I go in for angel funding or whether I keep bootstrapping this while doing consulting on the side is still unknown. It really depends on how much $$$ Braintrust starts generating with the PR and Marketing push I’m kicking off with this blog entry. That and the apetite for risk my wife OKs.

Ideally, I would like Braintrust to get a decent number of paying customers so that I can build out my team. There are so many more ideas I have to move Braintrust forward, but I don’t want to continue development at this point until I see whether this thing can truly fly at the level I need it to.

In Conclusion

Wow, what a ride. I’m excited, I’m jazzed, and I’m scared shitless. But, I need your help. No really, I do. Please go to Braintrust and set up a FREE account and give it a try. Then, email me and give me your honest, brutal, unfiltered feedback.

Also, please RT this article and help me spread the word. Countless hours have gone into this, I truly and deeply care about this, and I really want it to succeed.

Thank you for reading.

Categories: my thoughts.

3 ways to show screenshots of your product

As I’ve been working through and applying my 9 Principles behind an Effective Landing Page, I’ve been experimenting with different ways to “show” what Braintrust and Tout does. So far, I’ve found about 3 ways to effectively show people what your app does, and 1 that I’m absolutely in love with.

There is the “show the app in all its glory, and point to stuff and explain what is going on without getting in the way”

Braintrust Screenshot 1

Then, there is the “show the app in all its glory, but don’t count on people moving their eyes back and forth AND reading so put it the explanations on top of the app” way

Tout Screenshot 1

While this worked pretty well, I never liked the messyness this introduced. And then, I saw Panic’s amazing solution to this problem.

Screen Shot 2010 05 05 at 5.59.13 pm

So far, I love this one the best. It has these emitting red dots around interesting areas. The red dots emmit a red halo and basically call out “hover over meeee!!” and when you do, the explanation appears gracefully.

I haven’t gone on to implement this technique yet, but it looks like this tutorial on mimicking imagemap behavior using CSS is the way to get this going along with some jQuery tools tooltip action.

Categories: my thoughts, Principles.

How to efficiently follow up with new customers using Tout

Since both Tout and Braintrust are in their infant stages, I like to get in touch and personally talk to most new customers who sign up for one of the services.

I wanted to share with you my process for doing this, since it has been working out reasonably well for me.

  • I set up a template in Tout called “New Customer Signups.” Here is what it looks like:

Subject: Greetings from Braintrust

First of all, thank you for signing up for Braintrust. It is a new service and we’re really excited about it.

I wanted to reach out to you personally to see how everything is going with your new team Braintrust.

Since we’re constantly looking to improve our service, any feedback would be immensely helpful as well.

There are two ways you can give us your insights, you can either fill out this brief 8-question survey: http://survey.io/survey/a6db6 (it usually takes about 4 minutes to complete) or you can just hit ‘reply’ and write out your thoughts over e-mail.

I’m looking forward to hearing from you!

Cheers,

TK

Founder and CEO of http://braintrust.io

  • I don’t like to blindly send out these emails to every new customer. So, I set up a little link in my admin console so that for every new customer, I get a special link to Tout with the name and email pre-filled in. It looks something like “http://toutapp.com/pitches/new?name=TK&email=tk@email.com”

Pitch Stats

  • Based on the stats from Tout, you can see that I’ve got a reasonable amount of success. I’ve already tweaked my message a bit, and I’m sure I’ll be tweaking it more, but having the ability to track these emails and the stats around them has been immensely helpful.

Being able to keep track of these kind of emails for customer development has been hugely helpful. Both in terms of delivering a consistent message but also in terms of having actual stats so that I can iterate over the message.

Tout is a simple web-based application that helps you templatize and analyze your business emails.

Braintrust is a web-based private social network and discussion forum that helps organize your team’s conversations.

Categories: my thoughts.

How I gained more confidence as an Entrepreneur

When it comes to being confident as an entrepreneur, and being confident about the likelihood of your startup’s success, it makes a huge difference on how you got there.

The first way to get confidence is what I call the “hopes and dreams” confidence. You have relentless passion for what you are doing, and tons of hope and faith that you are going to make it big. You feel ready to take on whatever that comes up next. Good luck with this one.

The second kind, the one I prefer is the “I know what I know, I know what I don’t know, and I have a design for taking the things I don’t know and understanding them. Therefore, I am confident I will make it big.” This is where you want to be if you want to truly have a high probability of success and feel confident about it.

Its so easy to go around and say “I GOT THIS” and exude confidence — what I didn’t realize before is, it is actually EVEN EASIER to just say what you don’t know. Surprisingly enough, not only is doing the latter easier, it also increases the likelihood of my success.

Which category do you fall into? How did you get the confidence that your venture will succeed? Did you figure it out yourself?

To get your confidence the right way, just sit down, and write out what you don’t know and how you plan on attacking the things you don’t know. Believe me, at the end, you’ll feel way more grounded, confident and it’ll actually help the next time you’re on the bottom cycle of the entrepreneurial roller coaster.

For example, here is how I thought through it:

What do I know?

  1. I want to build technology that help people communicate using Braintrust.
  2. Building something awesome isn’t enough, I need to craft a compelling message that matches with people’s world view and figure out an effective and cheap way to distribute that message.

What don’t I know?

  1. I don’t know how to do PR and get featured in prominent business articles that are read by my target audience
  2. I don’t know how to run an effective social media campaign
  3. I don’t know how much money I should be spending on marketing
  4. I don’t know how to make Braintrust’s website show up first when someone googles “braintrust” or “group collaboration”
  5. I don’t know if my free plan should have ADs or whether it will turn businesses off.
  6. I don’t know whether I should start an affiliate program
    (The list goes on)

What I didn’t know but now know

  1. I didn’t know how to think about defining my price points. So I did some research, thought through it, looked at what others were doing and then established my principles behind a freemium pricing model. You can check out the pricing model for Braintrust to see the end product.
  2. I didn’t know how to build an effective landing page for my product. So I bought a copy writing book, read a lot of articles online, read some marketing books and then established 9 principles behind an effective landing page. Now, I’m pretty proud of the landing pages for Braintrust and Tout.
  3. I didn’t know how to think about an effective social media strategy. I’m still researching this and am getting close to establishing some principles around it.

You see, it is SO liberating to think through things this way. Sure, I don’t have all the answers, but I’m confident I will get to the right answers because I know what I don’t know, and I’ve got a solid principled process.

I’d encourage all startup entrepreneurs to blog about what you don’t know — chances are, we might find we have a lot in common…

Categories: entrepreneurship.

My 1-page Wireframe for Tout

As I was flipping through the pages of my Moleskine, I ran across my initial sketch of Tout. I’m so glad its there when genius strikes.

Its funny how Tout (originally called Pitch) went from a simple paper sketch to a product (in 3 days) and is now generating solid revenues. I love the web business. I love what I do.

Categories: my thoughts.

Tout integrates with Highrise

Although I use Tout to send out my customer development emails, but bulk of my relationships are managed in Highrise (the awesome CRM software by 37Signals).

Today, I spent an hour integrating Tout into Highrise so that the people I pitch to are automatically added to my Highrise address book.

Tout Highrise Integration

That wasn’t enough for me though, so I also integrated all the website-like analytics that Tout tracks for my pitches. Now, as events are tracked, they also automatically get added as Notes under the Highrise contact.

Tout Events Integration

Tout + Highrise has made an awesome secret weapon for my customer development and PR efforts both for Tout itself and for Braintrust.io

Categories: my thoughts.

The most fundamental principle for startup success

It bothers me how there is so much dogma going around on how to effectively build your startup. The latest was Paul Graham’s essay on how you should only work on organic problems.

Although I love his essays, this particular one inspired me to think about the principles around picking the right problem to solve, because I don’t think its simply about “my problem” vs. “others.”

While thinking through this in a principled way, I think I came across what I believe is the most fundamental principle for any business (including startups). The principle is: Focus on problems you can understand.

The goal of a startup

To get to this principle, I started with defining what the goal of any startup is.

The goal of any business, including startups is simple: Profit by providing a valuable solution to a problem.

If profit is not your goal, you are not running a business, you are running a charity, or even worse, a business doomed for failure.

Picking whether you should solve a problem that is organic vs. someone else’s problem is part of the design that achieves your goal. Similarly, Business models (Freemium, Free, Paid), Funding options (VC/Angel/Bootstrap), Platform choices, Distribution strategies (walled garden/open integration) are all other options that feed into your design.

Focus on problems you can understand

Now, to achieve your goal of Profit, there are a number of things you have to define in your design.

The most important thing that people back into without realizing it as they define the design is “the idea.” With luck, just focusing on the idea works for some, but as we all know, most businesses just fail since people are so focused on the solution a.k.a “the idea.”

Keeping the the most fundamental principle, if I were to create my business in a principled fashion, the most important thing for me to do would be to choose a problem I already understand or I can figure out how to understand.

Thinking about it at this level opens up a world of clarity and more importantly a world of possibilities for my startup to make profit.

For example, I don’t quite understand all the problems CEOs face, but I could easily talk to 30 of my CEO friends and get a threshold level of understanding of what their problems are. If I can do that, then I can most certainly pick one of those problems and solution it.

As you can see, it is not just about “scratching your own itch”, or picking “organic problems,” or just about attacking problems others may have. This is why Paul’s essay came off as too… specific to me, too dogmatic even.

Categories: Principles.

9 principles behind an effective landing page

It is no secret that I’ve really been struggling with marketing and customer development for BrainTrust.io (a conversation management tool for companies and teams). Along with trying to start a mastermind group to get myself some help, I’ve also been reading a ton of marketing books (All Marketers are Liars, 22 Immutable Laws of Marketing, Web Startup Success Guide, and the Copywriters Handbook) to get better at this. This entry outlines what I’ve learned after reading a handful of these books and after carefully looking at some of the most successful sell/landing pages out there.

As a follow-on the my principles for defining a freemium model, I’ve distilled what I’ve learned into a set of principles for creating an effective homepage that can sell your product.

Goal: Convince the customer to purchase your product

The most important thing to keep in mind:

Don’t think of this as a website. Think of this as a kiosk at a crowded mall. How would you design your kiosk to attract attention? How would you make the potential customer feel comfortable even though you are not a huge established department store? How would you, in 30 seconds explain what your product is, if you were speaking to the person? And most importantly, if the potential customer’s interest does pique, how do you make sure you sufficiently answer all of her questions?

Principles:

  1. Have a clear tagline that identifies and categorizes your product in the viewers mind
  2. Do not tell them what it is, show them
  3. Establish credibility, why should the viewer trust you?
  4. Tell a story. A good story communicates the problem you are trying to solve, and explain the benefits of using your product
  5. Define what you are delivering. Don’t try to explicitly define, relate it to something that is already defined in the viewers mind. Use “like” not “is”
  6. Have a clear call to action that leads directly into achieving the goal
  7. If the user has taken an action beyond initially landing on your page (eg clicking on a call to action) you’ve mildly piqued her interest, and chances are she has questions. PEOPLE ARE ACTUALLY READING AT THIS POINT. Have an extensive FAQ visible anticipating and answering all pertinent questions.
  8. Put off as many decisions as possible, make it frictionless to achieve the goal.
  9. Make it easy + encourage viewers to help spread your story

I’m still working to apply these to BrainTrust.io’s homepage, but it always helps me to establish principles before designing, so I’m posting them here for debate/discussion.

Categories: entrepreneurship, marketing, Principles.

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