About 3 months ago, I made a change to my schedule. I offered to drop my wife off in the morning, and pick her up in the evenings from the train station. At the time, it seemed like a small thing and more importantly the right thing to do. She has a grueling 2hr commute (each way) and easing the journey to and from the train station was the least I could do for her.

The train station was on my way to work, so it was a no brainer in the mornings, and its about 10 minutes from home, so even though I get home before her, the 20 minute pause in the evening didn’t seem like a huge deal at all.

My original schedule

As you probably know, I had a bit of an unique schedule already (before making the change). Since I am bootstrapping my own web business, and I am also ramping down at my day job, I essentially work two jobs. I generally wake up in the morning, work on my startup for a couple of hours, and head into the day job around 845 so that I get there just around 9ish. I work on my day job till around 5 and then head home to get more work done on my startup till about dinner time…which was generally 730. to make this sustainable, and to keep myself productive, I meditated twice a day for 20 minutes, usually at the point I context switched between my startup work and my day job.

I maintained this schedule through what I consider to be one of the most creative and productive times of my life. It is during this time that I conceptualized, designed and implemented Braintrust, Tout and atleast 5 other startup ideas that I haven’t talked publicly about yet.

The new schedule

At first glance, the change to the schedule seemed minuscule. In the mornings, the train station would be along the way, and in the evenings, it would be a 20 minute pause on my work. No big deal, right?

Creativity #fail

Wrong. While I got a decent amount of work done over the past 3 months, I realized that while small tasks were easy to get done during my startup office hours, I never was able to let loose and take on the bigger meatier goals that required my creativity.

I always left the bigger stuff for “later” — but later never came.

It turns out that the one thing I introduced into my schedule was an anchor. The anchor of the train schedule meant that I HAD to leave my home at 815, and so whatever task I picked in the morning worked back from that 815 deadline. Similarly, when I got home in the evening, I worked back from the 710 anchor and picked a small task that I could do in that timeframe.

Creative schedules cannot have anchors

The awesomeness of my original schedule was that there were very few anchors. I knew I could compensate for being a little late to my day job in the morning, so I never worked backwards, I just sat down and worked to a natural stopping point.

Similarly, in the evenings, it was OK if dinner started a bit later, so I always was able to come to a natural stopping point.

If you want to foster creativity, get rid of anchors in your schedule. Block out days where you don’t have anything scheduled — so that you can start and stop your work naturally — the results will be immense.

Changing back my schedule

I shared this reflection with my wife. Now that we are moving closer to her work in about a month (hopefully), her commute will go from 2 hrs to 30 minutes.

She was extremely nice to take on the train station grunt for the last month that we are here, so that I can switch back to my creative schedule.

Today is the first day I’m back on my new schedule, and I feel great.

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.

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.

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…

Do note though, 37Signals mantra here probably roots back to a saying my Dad, also an entrepreneur, has always said to me: “Necessity is the mother of invention”

Either way, here’s the problem I solved with Tout: as I’ve been ramping up customer development for Braintrust, I realized that typing, copying, pasting, re-typing all these emails was becoming a huge pain. Even worse, it became even harder to keep track of all these emails.

“There had to be a better way!” — and while there are tons of CRMs out there, the simple “get in, get out” type of solution didn’t exist. So, I decided to create one.

Introducing Tout – the simplest way to templatize and track (like you do for websites) your customer development emails. It helps me create e-mail templates, send emails quickly, and track when someone’s viewed my email, and whether they clicked on my link. It also lets me track whether my overall email was a “success” or not.

It took me about 1 day to get the app working to fit my own need. After realizing this could probably help other people, it took me another 2 days to get it production ready. WOW!

I think we’re at amazing times right now. With all the different “common services” startups cropping up, building, releasing and opening up shop for a web application has never been easier.

Here are the common services/technologies I leveraged to take Tout to market in 3 days:

All of my development is on Rails, and Heroku puts Rails on steroids. Thanks to their amazing cloud infrastructure, I had to do ZERO sysadmin stuff and was able to get my app online in literally 3 commands. More importantly, setting up DNS, E-Mailing, and SSl was all done through the web UI as well. I highly recommend them for starter applications, especially ones that are still testing out the market.

The only downside for Heroku is that they have no way to support real-time applications (i.e. run an XMPP or NodeJS server to push out real-time updates) — can you guys start working on this?

Even though the biggest “feature” of my web-app is sending emails, I had to write next to no code for actually sending out emails or even configuring e-mail servers. All of this got taken care of by Sendgrid.

They were also very diligent about validating my site and making sure I was compliant with CAN-SPAM laws and ensuring this doesn’t turn into another spamming machine (Thanks Jose!)

Tout has a premium feature, and charges credit cards, handles recurring billing and even sends out invoices. However, I didn’t have to write more than about 50 lines of billing code. Chargify takes care of all of this — all I have to do is build out hooks to keep the subscription level of the customer up to date.

The reality is, it has become so ridiculous easy to take web applications to market now that I don’t have to spend time working on plumbing — instead, all of my time and energy goes toward the creative aspect of the product — which is the way it should be.

And, if you’re wondering what Tout looks like, here’s a 2 minute screencast showing what it does:

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.

First, so that you have the context, here is the 3-minute video explaining what they are all about. The basic gist of which is “You can actually achieve a whole lot in FOUR YEARS” along with the usual “this may be our last chance to save the planet.”

The video got me thinking… 4 years is indeed a long time, heck, I’ve achieved so much in the PAST 4 years, what will I be achieving in the next 4? And THAT is when my epiphany hit me.

See the thing is, I have been SO focused on getting my business off the ground, I haven’t really been thinking about a timeframe beyond this week and the next… forget 4 years.

Sure, I’m all about “the dream” and so is this blog, but my dream of attaining freedom and never having to worry about $$ is this idea that is in the “future” somewhere — there is no timeline associated at all. I just know that this is my best idea, and this will get me there… eventually.

However, I think that is the wrong mindset to have. I think it is easy for entrepreneurs to get sucked down to the day to day, just trying to make sure you get that demo video out, or that landing page updated and then end up completely falling out of synch with your goals.

I’m not proposing that you make a 4 year project plan and a path to get there However, I am proposing that you sit down and think about where you want to be in 4 years. What does that feel like? What does your business look like? Having that north star will give you perspective, and having that perspective will make you prioritize today better.

So. Where do YOU want to be in the next 4 years?
I have no idea, I actually need to sit down and think this one through.

I am a single founder. I haven’t diagnosed why, but after co-founding two prior startups, I decided that I like it better being the sole founder. While I can code, design, and have picked up some business acumen, there are still deficiencies that you face when you don’t have a sidekick. To make up for not always having a co-founder to bounce ideas off of, I made up an imaginary friend named Charlie (No, I am not joking).

However, Charlie can only go so far, and its probably kind of weird,  so to compensate I’m starting a Single Founder “mastermind group.”

I mentioned this a few months ago on Hacker News, and now am talking to a few people that expressed interest. It looks like it is going to be a bit of a tango dance to zero in on a like minded group of people to create the mastermind. I’m posting this blog entry to widen the audience a bit and make sure I talk to enough people and get to a real quality group to form the mastermind with.

I believe that part of this is going to be serendipity, but it doesn’t hurt to have some principles established either. Here is how I’m envisioning it to work:

My goal is to bring together a small group of like minded single founders.

Ideally, this is the profile of people I am looking to bring together:

1. Actively working on an idea
2. Focusing on it full time or on a track to focus on it full time
3. Has an actual skill, i.e. A graphics designer, or developer, or a pro marketer — NO IDEA GUYS
4. Has a blind spot/lack of skill in a recognized area (for example I am working hard to develop my marketing and customer development skills).

Given the principles above, I think the value of the group becomes clearer. You’ll contribute to the group by helping others on what you’re good at, and you’ll get value by getting help on what you’re bad at.

Once we get the initial group together (which will be a bit of a tango dance), we can work to figure out where we are deficient as a group, so we can work to recruit more people from there. I’d probably want to limit the group to about 11 people. The key idea here is to give each other support, help each other, and just be available to the group.

The main commitment would be a 1hr conference call once a month or so, we can define the format later. And, if the group agrees to it, a private community online where we can talk about stuff in between meetings.

If you are interested, please get in touch with me, and if you have any ideas on how to make thjs better, just comment below.

Last night, I was out with three of my closest friends. After a few drinks at some random pub, getting dinner on curry row, and hitting up a roof top party, we decided we needed to take the night to someplace a bit more low key. We all agreed that we wanted it to be a wine bar. I decided to take them to The Immigrant.

Now, there are literaly HUNDREDS of wine bars in the city, many highly rated on Yelp. The Immigrant was not even within the vicinity of where we were and yet, that was still everyone’s place of choice. Why? Because I had a story to tell them about this particular wine bar. It wasn’t much. I just said “its this awesome wine bar, they have a reasonable selection, but its run by these two guys that run it like they OWN the place. They really go out of their way to make sure you’re happy.” That story was enough for my friends to get back on the FDR and make the trek.

What does it mean for startups?

It means that having a character, a story, a personality is SO much more important that your idea, and your product. It seems like there is SO much emphasis on these nitty gritty details about your business plan, term sheet, acquisition strategy, people are forgetting the single thing that will get people to use your product: A STORY.

I drive a BMW because I buy their story of a joyful driving experience. I use Twitpic over the million other photo sharing services because I think Noah Everett is a great guy and has a great story. I use 37Signals products because I buy their story that says simple tools can help you get shit done. And finally, my friends all agreed to go to the Immigrant because they bought the story of choosing the place where the owner is serving you and REALLY taking care of you.

The moral of this story

Now the important thing is, just telling your story isn’t enough. You have to actually back it up. I wouldn’t keep using 37Signals if their tools weren’t actually simple. And similarly, my friends wouldn’t have had a good time if they didn’t get the experience my story promised. A great story will attract people to your storefront, but a great product is what will make the sale.

As for The Immigrant, when Jason (who indeed turned out to be one of the owners) saw us trying to get in through the door in the crowded place, he ushered us in, and lead us to the back where there was plenty of room. He shook my hand and said “its been a while!” and then proceeded to take care of my friends. When we asked him about the crowd, he said “yeah, we’ve been open for 2 months and its starting to get real busy.” That’s no surprise. That’s a great story and a great product in action right there.

The moral of this story? Its okay for you to create the 100th Twitter client or iPhone app of the same genre, just make sure you have a compelling story to tell. That is what people want the most.

While thinking through a pricing model for BrainTrust, after numerous failed attempts (including the one shown on the site right now), I decided to write out some principles first.

1. There should be a free plan to give the casual user a taste of what we are about. Anything given for free should only give a taste, at a clearly limited scale. Not all features should be given out in the free version.

2. There should be a “recommended” plan. This plan should cost what we need the majority of our user base to be paying. It should also have the appropriate features to give the BEST OVERALL EXPERIENCE our product has to offer.

3. There should be a “cheap” plan for the skeptics, that includes all of the essential features but at a limited scale. Remember, we’re only giving a few limited features in the free plan, skeptics can upgrade to the chapo plan to get a feel for all the features. However, the cheapo plan still doesn’t provide the “best experience” — thereby giving the customer an incentive to upgrade to the recommended plan once their concerns have been alleviated.

4. Finally, there should be a “hail mary” plan. This is the fully equipped, no expenses spared version of your product at a triple digit price, to test out the upper limits of our market and our overall pricing assumptions.

5. Our customers should be able to take any of the paid experiences for a trial run. The trial run should be long enough for the custimer to run through all the important use cases the product supports.

6. There can be “filler plans” that give our customers a healthy gradation to pricier plans — so that our customers can slow upgrade to larger scales without having to jump straight to the “hail mary” plan.

I hope this helps. I’ll be sharing how our new pricing strategy works out for BrainTrust once we go live.

In the mean time, comments, thoughts. debates are all welcome.