This is one of the problems that Braintrust has been solving. First, it does so by centering the conversation onto one page. But that wasn’t enough, today we released a feature that also helps you keep track of what’s “new” instead of having to scroll through an entire conversation.

The concept is totally simple. We’ve added a simple counter of “new messages.” So, when you log into your Braintrust account, you get to see the number of new messages that exist in each of your Braintrusts. For example, over here, I can see that there are 4 new messages in my Team Braintrust, but nothing new to check out in my Customer Braintrust.

Once I click through to the Team Braintrust, I’m shown all of the important conversations happening within my team (as it has always shown). But now, notice the little red circle underneath the second conversation. That tells me that there are two new messages in that conversation, so I should probably check it out and catch up.

Now usually, once I went into one of the focused discussions, I’d usually just scroll through the whole page, where the entire conversation has been neatly pulled together for me. For smaller conversations, it was pretty easy to see what is new. However, as conversations started to grow, we realized how it gets hard to see “just the new stuff.” And so now, you’ll see we highlight every new message in the conversation with a little icon.

Simple.

Now, with your Braintrust group discussions, you can get catch on the context of a conversation and see what is new all in a few seconds.

Who’s in your Braintrust?

So, with that said, I was inspired to introduce a new feature in Braintrust that I’m really excited about. It is called Braintrust Feedback. Now, the goal of Braintrust has always been to help small tight knit groups of people share ideas, get feedback and communicate better so that they can make great things happen. Although till today, you could always write a comment to give feedback to what someone has said, it didn’t seem like enough.

So now, with just 2 clicks, you can give a wealth of feedback to each share. Here’s how it looks:

As you can see, the design starts off with the basic fundamentals of Facebook’s “like” and Twitter’s “RT” but is taken a step further. It tries to replicate the same natural conversation pattern, where you can easily give either a “Good” feedback or a “Bad” feedback.

I’m really excited about this feature, I hope you are too. Try it on your Braintrust today.

While there is a pretty healthy discussion thread on Hacker News about this latest not-so-classy move by Posterous to deem all of their competitors as dying platforms, I’m not here to talk about that. I’m here to talk about an alternative strategy for Posterous that they should consider for their larger vision.

What I perceive Posterous to be doing now

Now, based on what I have seen, it looks like their goal is to become the next WordPress.com. They’re incorporating the same features (e.g. pages and themes) and they’re trying to (seemingly) convince users of WordPress.com-like sites to import their blog onto Posterous.

This seems kind of a waste to me. I mean…why bother? Why bother creating a company, and raising funds, and working as hard as you do (based on their twitter streams, they look like they’re really working their ass off) when all you’re doing is by and large going down an already paved path?

An alternative for Sachin to consider

If I were CEO, I would stop this chasing game that Posterous has going with WordPress.com. I think there is a better strategy to attack the blogging and CMS market. I’d go after the millions of businesses, startups, and individuals that do three things today:
1. Pick WordPress (Free)
2. Hire a consultant to do the “design” and “coding” ($$ Spent)
3. Research, analyze and implement the elements that helps the person achieve their specific goals ($$ and Time Spent)

This means that instead of creating a generic blogging system that just copies WordPress features, I’d focus Posterous on creating the “starter” blog for a set of verticals. A starter blog that has already been optimized to achieve my desired business/personal goals.

For example, take my blog. I’ve analyzed countless blogs and tried out hundreds of templates until I settled on this design. This design is optimized to the brim to explain who I am, re-share my content, and most importantly drive traffic to my products. It took hours to get to here, and its probably not even perfect.

If you were an entrepreneur that didn’t know much about coding, wouldn’t you PAY for a blog that has already been optimized to help build your personal brand? If you were a startup, wouldn’t you PAY for a blog that has already been optimized to spread your story?

So the idea is simple. If I were the CEO of Posterous, I’d create a set of ready-to-go, tested, and optimzed ‘starter’ blogs that has the right bells and whistles for each of these individual targets:

1. A startup looking to promote their story (have it pre-set with a “About Us” page, a sidebar section to explain their product(s) and what they do, and Twitter/Like buttons to promote the posts

2. An author looking to promote his/her (e)book. Have an “About the Author” section, have excerpts/reviews on the sidebar, and a way to profile sample chapters as blog entries along with a super easy big call to action for buying the book from amazon.

3. A small business trying to attract locals. Have a clear display on the sidebar for location, maps, hours, and phone number. Have a section showing off pictures of the business. Have custom post types for Sales, Events, and special SEO sauce optimized for the given zip code.

And we all know, there are a good 10 more solid verticals like this. Think schools, community groups, and even non-profits. There are probably niches within those that they can further optimize for and charge premiums on.

With an offering like this, not only will you solve a real problem (people like these having to create and customize these sites from scratch AND having to figure out what the right things to show are — even though its well known), you ‘ll be solving a problem that people are already paying through time and $$ for.

Sachin and Gary are both talented and are working hard. But maybe they’re just too caught up in the tasks. Step back and take a look at the forest.

In contrast, making the decision to quit my day job back in March was a no-brainer.  I reflected on what I wanted to do with my life, and I knew in my heart that building startups is what I love doing. Knowing what you want is important, and sometimes hard, but now that I’m working through getting what I want…well this is where the rubber meets the road. And…it’s hard. To craft my plan, here’s how I went about doing it.

Answering the obvious questions:

I started with answering logistical and concrete questions like:

1. Are Braintrust and Tout the right products? Will it make money for me?
2. Do I need to focus on one product to succeed? Is now the right time to focus?
3. To make these products a success, do I need to bring on a co-founder? Is now the time to build a team?
4. should I look for funding?
5. should I apply to ycombinator?

   Note: I think both of these ideas are pretty strong in my opinion and it is unlikely I will kill either. I see no reason I cannot continue to grow both in the long run with short periods of focus on each.

Although thinking through these questions was helpful, and talking to people gave me a ton of insight, I realized that I was getting very fixated on the financial questions, and even worse was jumping to common solutions like “oh.. Just go look for funding.”

Transcending to the higher-level questions:

I paused.. And pulled myself up to the larger questions at play… What is it that will make me happy? How do I want to be spending my day? What is really the larger goal at play here? Fortunately, I already had the answers to this. When I set out on a conscious journey to build a startup, I wrote down my personal goal: “Be able to do whatever the fuck I want.”

It was funny. After reading that, it all became so much clearer. I’ve been having to prepare for months if not years to become non-dependent on an employer… Do I really want to turn around and get funding? Do I want to take the leap from one master and jump to another?

All the little questions became irrelevant.

Of course I don’t want funding. Of course I should work on my ideas freely. I don’t want to take on any masters. I want to be Bootstrapped, Profitable & Proud (inspired from the series that 37Signals has been running).

Hopefully getting what I want:

And so, armed with the clarity of knowing what I want (be able to do whatever the fuck I want), I defined my transition strategy. I know where I want to be…just read any one of those articles on the 37Signals blog. And I know I can’t get there in one fell swoop. Its going to take some steps, and some transitions. But on a 10-year timeline, I think I can get to a great spot (hopefully). Here’s what my transition looks like:

• Focusing on each of my ideas 3 weeks at a time. In about 6 months time, I’ll re-evaluate which idea should get less and which should get more attention.
• Spin up independent consulting for 50% of my week. If you know someone that needs help with UX, UI, Product Design or just to take an idea to a prototype, I’m your man, please send them my way (tawheed at gmail).
• Scale back on expenses. This means getting rid of my beloved BMW, moving to a smaller (but still cozy) place, and spending less money on going out.

I’m excited. I want to be Bootstrapped, Profitable, & Proud. I want the freedom to do whatever I want. I want to be my own master.

How I originally used Basecamp ToDos

I keep a project for each product, and over the past year and change, my To-Do lists have served me really well. I always kept multiple ToDos based on the general area of focus (e.g. marketing, a major feature, a general theme). Here’s a snapshot of what my completed ToDo Lists were called:

As you can see in the picture above, Basecamp has been right along with me for the whole ride. But surprisingly, after logging into Basecamp today, I realized that I hadn’t logged in for nearly a month! It’s not like I was on a vacation over the past month (far from it) — I had been doing lots of work. However, it didn’t occur to me to refer back to my ToDos.

This wasn’t OK though — because I still recognized the restless feeling in my OCD self. That feeling of angst, that fear that I’ve got lots of activities going on, but I’m not 100% sure if I’m achieving the goal, and I’m not really tracking what I’m doing and where my time is going and this could be bad. But at the same time, I just couldn’t get myself to start creating more ToDos based on what I was working on.

My new design for ToDos

Upon reflection, I realized that my whole paradigm of working has changed now that I’ve got two products that are beyond just defining the MVP but at a point where they need more refinement and more rinse and repeat.

More concretely, now that both Braintrust and Tout are starting to see some traction, it is no longer about just rolling out the minimum viable product and seeing whether it sticks. It has become more about setting some specific goals for each product and honing in on the set of tasks that will effectively achieve that goal.

And so, I started to reorganize my ToDo lists based on the specific goals I had already set for my products in my head. Once I did this, the actual tasks started flying in. My ToDo list finally aligned with my mental model, and I knew the movie of what needed to happen to achieve each of those goals. Basecamp felt like a friend again, and here’s how it started to look:

In the picture above, you’ll see how I split ToDo lists into the higher level goals I’ve set for Braintrust (this is a sampling, there are more) — and you’ll also see (vaguely — I’m still fleshing them out) how the specific tasks can add up to effectively achieving my each of my goals.

I think this “new” way will be really awesome in both sticking to my goals and keeping me honest on thinking through how to achieve a goal — instead of just attacking individual tasks that do not amount to anything.

Thoughts/Feedback are most welcome! How do you manage your startup’s ToDo list?

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.

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

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.

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.

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”

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

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

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.

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”

• 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.

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.