“Great Customer Service” is not a real goal

After nearly a year of growing Tout, I went from doing all our customer service via email — to getting a ticketing system — and then to hiring someone for “owning” community management. Through this time, I’ve come to learn one thing: there is no such thing as great customer service.

Naiively perhaps, I always figured that there was one true way to do customer service. You give the customer what they want, as fast as possible and they’ll be happy, they’ll pay you, and everything will be fantastic in the world. Simple, right?

Wrong. It turns out much like most things in business, what you define your Customer Service experience to be is determined largely from a series of tradeoffs that you determine based on the goals of your business.

As we’ve grappled with the different challenges around meeting our customer’s needs within the natural limitations of a Startup, here are the key principles that I’ve followed to guide my decisions so that we can get to providing “Great Customer service.”

#1 – Know your Priorities

This may be obvious but in practice we tend to forget this all the time. When it comes to your customers, and taking care of them, know where it falls in terms of Priority. When it comes to choosing between handling the 100 E-Mail tickets that came in today vs. Releasing that 1 feature that will get you another 5,000 users, know which one is more important.

The idea behind prioritization should bubble upward and downward as well. Meaning, you should know how you want to prioritize your 100 tickets (priorities bubbling down), and you should also know how important customer tickets are on a given day, week or month with respect to your higher level (bubbling upward) business goals.

You have X number of hours in a day, by explicitly prioritizing, you can atleast tell yourself the truth. There is a huge difference between working on your next killer feature while worrying about your customer tickets in the back of your mind (you know that nagging feeling) VS. working on your next killer feature and NOT worrying about your customer tickets because you’ve made an explicit decision in your mind.

I don’t think there is a cut and dry prioritization here — which is the basic truth everyone should come to terms with. Just know what YOUR prioritization is. Given the stage of your business, your customers may not be #1 — and that is OK — as long as it is explicit.

#2 – Know the different ways you can say “Yes” to a customer

This one took a while for me to realize and define. The goal of a customer interaction is not to give them what he or she wants immediately regardless of what your company can afford to do — the goal is to make the customer feel “good” or even “Ok” with the situation if you cannot get to “Great.”

We often think that the best service organizations are the ones that always give the customer exactly what they want or go above and beyond. Not true.

I think the best organizations know how to make the customer feel good about the situation where they may have been originally feeling bad, and then work with the customer to solve their problems on a timeline that is realistic for everyone.

So, remember that saying “yes” is not the only currency you have. Figure out what else you can offer the customer that can alleviate their concern until you can solve the root of their issue.

One example of this is telling the customer “I’m sorry, but we can’t help you immediately because of X but I’m going to keep you updated through the process, and in the mean time, we’re going to comp you for X months.”  – giving your product gratis is a form of currency. So is sending them a hand written card, or giving them a phone call instead of firing off another Email.

So to summarize, figure out all the different things you can do for your customer — it’ll give you a lot more flexibility and remove a lot of stress for you.

#3 – Know whether you’re going to for “quick fixes” vs. “systematic fixes”

This principle actually doesn’t just apply to Customer Service, but can apply to any function in your business. As you’re working through your tickets, it can get very easy to just “do” them. In fact, thats what us human beings love doing — we love to “do.” It feels good.

Well, pause and take a step back. Its important to figure out what strategy you want to follow as you’re addressing customer issues. For any given customer problem, you always have the option of “going into the database” and “doing a quick fix” by “flipping that field.. or deleting that record” — OR — taking a step back, figuring out how many tickets are of this same nature and seeing if releasing a quick bug fix or feature enhancement would solve the problem for not only the tickets from today but will have a serious impact on your ticket volume overall.

Quick fixes are easy, fast, and gets your customer to a happy state. Systematic fixes preemptively solves the next 10 tickets that are going to come in.

Given the amount of development resources you have and the time cost of the person doing tickets — figure out which strategy you want to be following.

#4 – Try to be more “Proactive” vs “Reactive”

Over here at Tout, we think of anyone we hire around Community and Customer Service more as Content Creators and Communicators rather than “Service Reps.” In fact, I hate the term “Service Rep,” “Customer Service Associate” or anything of that nature — it is boring, uninspiring, and it just plain sucks to be in roles like that.

With that said, most Startups (and companies) take a more reactive approach to Customer Service. They wait for tickets to come, they resolve them, and then they move on.

We hate that. We hate the idea of only interacting with our customers when something goes wrong — and even worse, waiting until they write in about something going wrong.

So, our Tout Happiness Officer (we’re hiring one more by the way), not just responds to tickets, but is responsible for developing content for Tout University where our new customers can learn how to use Tout to be successful. She’s responsible for proactively reaching out to customers so we can learn how they are using Tout and feature them on our blog, and even flesh out our Knowledge Base where customers can go for quick help.

This principle reminds us that solving just this customer’s problem today is not success, but success is putting the systems and resources in place that can help the next 10 customers.

In Conclusion…

We have all these misconceptions and frustrations around Customer Service. I think it has become one of those phrases and roles that we take for granted without stopping and thinking… well — “What does it really mean?”

Our team works and thinks hard about customer service every day. There are things that frustrate us, there are things that we work hard on, and there are things that are working quite well. It ain’t perfect but atleast with these principles, we’ve started to get an understanding of how we want to serve our customers and how we can get there.

In fact, the next thing we’re doing to make our service more excellent is to hire our first full-time Tout Happiness Officer. If all these principles and the things I’ve talked about here are interesting to you, drop me a line.

As an Entrepreneur straddling both coasts, I get asked the same question almost every day: “So are you going to stay in Silicon Valley or go back to New York?!” The questions intensified when I went back this past week, so I decided to reflect on it a little. I had always been bullish about New York but after spending this past summer in California, and after having spent about 18 months in California back in 2006, I thought I’d compare, contrast and reflect here.

The New York Startup Scene is Important

Not to be overly dramatic or anything, but the New York Startup Scene is going to be incredibly important. But after experiencing Silicon Valley all over again, I came to the realization that New York is never going to be Silicon Valley, but it’ll be important for a whole different set of reasons — that is if New Yorkers choose to let it. Let me explain by drawing a parallel in the Finance industry.

When it comes to the financial industry, most think of New York to be the center of that world. Images of stock brokers, wall street, and huge bonuses come to mind. The opening bell in the New York stock exchange beacons the start of trading for the worlds complicated financial ecosystem.

However, there is one other key “center” that actually takes precedence over New York. Not becuase of the volume of trades, or for being the source of actual innovation, but because of its location and it’s reach in terms of distribution. London, because of its relative centrality to all timezones, serves to be the true center and financial mediator of our advanced financial world.

The brokers in London, through the course of their workday, have the most access and therefore the most liquidity with all relevant financial markets. In an industry where real time connections drive profits, London’s ability to get on the phone with any important financial market through the course of their natural workdays makes it the real center of the financial world.

With that said, I believe that while Silicon Valley will be the center of pure technology innovation for the foreseeable future, New York is quickly becoming the London of the tech industry.

Let’s think about that analogy for a second. Undoubtedly, Silicon Valley has been the chief source of grand technology innovation for the last 50 years. And because of that, we’ve become incredibly good at rolling out new and exciting applications of that pure technology to solve real industry problems.

However, much like how New York is at a disadvantage in reaching out to world markets during their official trading hours, Silicon Valley faces a similar disadvantage due to lack of convenient access to domain knowledge in industries in need of tech innovation.

Enter New York, the London of the tech industry. With unlimited access to countless industries, any meetup, bar, restaurant or social event you attend will be filled with domain knowldedge from atleast 5 different industries.

In this era where pure tech from Silicon Valley allows people to release beauiful, functional, and diruptive applications in just 3 days, it is no longer about tech innovation, it is about problem space innovation. This makes New York very very important.

New Yorkers: quit trying to catch up to Silicon Valley

So New Yorkers, my advice to you is to quit trying to mimic, model or catch up to Silicon Valley. If New York is going to become important in the tech sector, its time you do what every nerd does when they come of age and finally stop trying to mimic the popular kids: Play to your strengths.

About four months ago, I packed up my bags, said goodbye to my friends, family, and wife in New York and ventured out to California. I had been fundraising for Tout and during that process made the decision to join Dave McClure’s 500Startups accelerator program.

This post outlines my key thoughts and reflections on the overall experience of being part of Batch 001 of the 500Startups Accelerator Program.

Note that this is a seriously long blog entry, so you may want to skim through the headlines first and then zoom into the parts you are interested in.

Thoughts on startup accelerators in general

Tout is not my first company. It is actually my 3rd startup, and the 4th company I (co)founded. Out of the 4, one completely failed, one had an exit and one proved to be a very successful family business for a long period of time. So naturally, whenever I came across suggestions to “apply” to accelerators/incubators like YC, TechStars or any others, I always felt that it’d be more of a distraction.

However, when Dave offered to invest in Tout he also casually asked “why not spend the summer in California and do the accelerator program?” I really had to stop and think. Hmm… why not?

After having gone through the program, I’ve found that the maturity of a company and the level of experience of the Entrepreneur is by and large irrelevant when it comes to deciding on whether to do an Accelerator.

An Accelerator gives you five key things (in order of value):

1. Initial investment (although it may be costly)
2. Advice/Guidance/Mentorship
3. A natural forcing function (i.e. Demo Day) to rile up the troops and perform at non-human levels
4. The “social card” that only Medical Students and Surgeons enjoy to get out of any of your social and life obligations
5. Credibility for PR, More Investments, Recruiting

Now, as with any other business decision, anyone that comes to me these days asking “Should I do YC/500/TechStars?” — I basically tell them “It depends on what your goals and needs are for your business.”

So if you are pondering whether an accelerator can truly accelerate your business, you should figure out the top 3 Goals you have for your business and then figure out whether any of the things above can help you achieve your goals faster. After you’ve figured that out, it becomes a simple Cost/Benefit analysis of whether the amount of equity you give up is worth the amount of “acceleration” you receive. Simple.

Thoughts on 500Startups

I honestly don’t know what the true “pecking order” in the world is for 500Startups vs. TechStars vs YC and frankly I don’t care. I viewed selecting accelerators the same way I viewed Fraternity rush back in College: You don’t go pick the Fraternity with the biggest house, the raddest parties or the hottest chicks, you pick the house based on how good of a time you have AFTER the rush event is over when you’re just shooting the shit with the brothers. You pick a Fraternity because of the people, and you should pick your Accelerator program or even your Investors based on the people. Its all about identifying common values.

Given that benchmark, I give 500Startups an “A-.”  Over this past summer, I’ve met some of the most humble, most interesting and most intelligent people I have ever come across — all qualities that I deeply value.

You know you’re surrounded by great people when the ideas they are working on become irrelevant. The ideas become irrelevant because as you talk to them you know that sooner or later, one way or another, this guy (or girl) is going to figure it out and make it rain. And I think this very aspect of 500 is what makes it more than just another accelerator program or investment fund — this very thing is what makes it a Family. A Family that is fornicating like mad to selectively establish blood lines across the globe.

“How does it feel to be Startup #89 in Dave’s 500?”

I used to get insecure when people snarkily asked me this question in the beginning of the summer. Now I just laugh.

500 is a family. When you start to internalize the concept of a VC fund that is building a family you start to understand why that is a stupid question. Most investment funds are built to function in a 1:N interaction model. Dave is building a system to meet the needs of portfolio companies that fosters N:N connections rather than the traditional model of 1:N connection that Partners in funds usually stick to.

When you start to think about building systems for N:N connections, everything including the scale at which you can execute drastically changes. Things such as SMASH Summit, Inbox Love, 500′s Mentorship program, and even the Mailing List is just the beginning of building a system that supports these N:N connections — and I’m excited to see where Dave takes it.

So just in case you want my official answer: It feels great.

Key Lessons Learned

Overall, the accelerator program was one of the best things I think I could have done for the long term viability of Tout. While we were slightly ahead of most of the companies in the batch in terms of product, Tout was way behind in terms other core foundational things such as having a team and having a full understanding of why we exist. Going through the program helped myself start to clarify our long term vision, think and re-think through the “A-Z” acting as if we just started, and even start to build out a core team around the company.

With all things turning out “as expected,” I still think its important to always pause and reflect. So, here are the high leven take aways that I think are important to mention:

Lesson #1 – In business, a sprint is almost never worth it.

Through the summer, Derek and myself ran a serious sprint. We lived and breathed Tout24 hours a day, pretty much checked out of our social responsibilities and cranked out features, code and updates at a ridiculously ridiculous pace.

Needless to say, when Demo Day arrived and went away, we slowly came out of trance and came to realize that the level of productivity we saw through the summer didn’t come at a low cost.We were totally consumed by Tout and I don’t regret a moment of it. But if I were to do it again, I’d figure out a better way to harness all that energy and make sure we ran it more like a marathon than a sprint. Unless you are building a “built it and flip it” company — something I am fundamentally opposed to anyway, you shouldn’t run a sprint.

Lesson #2 – Demo Day is a day, which means there is a “Day after Demo Day”.

This is one place where I have to seriously ding Paul and Dave. To us Freshmen, the way Demo Day was described to us was sheer mania. Investors, craziness, pitches, checkbooks, checks being written, deals getting done, cow bells being run because of the funding coming in.The truth is most of the things that will happen ON Demo Day will happen because of what you did leading up to Demo Day (by forging relationships and starting conversations) and anything else that you expect to happen around fundraising will actually happen AFTER Demo Day as you start to have more detailed conversations.

You can argue here that “Wait a minute! Thats not how it works at YC Demo Day… people really do write checks on the spot” — yes, they do.. but thats only for the Top 10% and maybe 5% of the class. And let’s be honest, they didn’t need Demo Day to make that happen, that was going to happen anyway.So, related to #1, realize that there is preparation to be done leading up to Demo Day (always be raising), and make sure you save your real energy for the weeks after Demo Day. It is a marathon, not a sprint.

Lesson #3 – An Accelerator is just the Lubricant. You still have to have the Sex.

Pardon me for being explicit here but there is really no better way I can phrase it. Within the first week of the program, I came up with my “wishlist” from 500. Meaning, the accelerator program can enable you to move faster through your game plan, but you still have to drive the car, run the company, put in the gas and actually know where you want to go.With that said it is also important that you hold the people running the program accountable and give them feedback (Dave and Paul will be getting a book from me in addition to this blog post). You gave them a good chunk of your company, make sure you make them work for it and you get your moneys worth.

Lesson #4 – When it comes to Early Stage, California is a better bet even if it is temporary.

I’m a New Yorker. I have lived in New York since age 10. I went to College in New York. I love the New York tech scene. In fact, that is where I got my start.

However, I have to be honest. When it comes to early stage, when you are at the very beginnings of your idea, you are going through the “Shawshank Crawl” — you’re dealing with all kinds of shit, figuring things out as you move along, and there are tons of unknowns and very few things working.

When you are at this stage and unless you are seeing instant success (i.e. you are the rare lucky one), there is only one kind of investor that truly understands what you are going through and has the mental capacity, context and extrapolation skills to figure out whether you are a good bet or not. That investor is the guy (or girl) that has built a company already, been through the same “Shawshank Crawl” and now can invest in you.

New York has very few of these investors. Instead, what you have are investors that ask you questions that you obviously do not have answers to because they just don’t know any better. Its the same reason why Boston lost the Zuck, and the same reason why New York still loses great Entrepreneurs today.

This will get better. It will only get better as more NY Entrepreneurs exit and as more Entrepreneurs that came FROM New York exit (I’m looking at you Matt M.) and then go back to NY to invest. This will also get better as more California investors look to NY companies and set up shop there (this is starting to happen to).

So on a macro scale, New York is getting better. But when I’m giving advice 1on1 to an Entrepreneur I believe in and care about, I tell them: Go to California. Spend atleast a summer there.

Lesson #5 – Using the Accelerator as a point of leverage works

Regardless of which state you are actually in as a company, being in an Accelerator paints the picture of an extremely early stage scrappy startup. So make sure you use that to your advantage in all your negotiations. Use it with customers to make them feel like they’re “getting in early” on something new and exciting, use it for recruiting to show not only as an opportunity to work for the company but also be part of the larger accelerator, and definitely use it to get price breaks.At numerous points through the summer, each of our batch mates were able to negotiate significant discounts with various vendors for the WHOLE class just by asking for it. It’s free exposure/marketing for them and well its money saved for you and your class.

The Cliff-Notes-Version

For the anxious, here is a summary of the key principles I defined. You can read the rest of this (lengthy) article to read about the thought process and thinking behind each of them.

1. Only hire for the core of your business
2. Don’t hire for Skills, focus on VALUES and ABILITIES
   
3. Incentivize for all senses (i.e. its not just about the paycheck or the equity)

Why should you hire someone?

It may seem like an obvious decision to a lot of startup Entrepreneurs to just go hire people, but I think it is important to recognize that there are a number of different ways to go about staffing. With the number of service businesses that exist today, it is possible to literally outsource every single business function in your company — everything from design, development, marketing to the obvious stuff like legal and accounting.

While for most technology startups it is a no-brainer to have an internal development team, I think its important for you as a startup Entrepreneur to stop and think through which aspects of your businesses should be “core” and which aspects you can get away with contracting or even sourcing from service companies.

With this context — I established my first Principle – Principle #1 – Only hire for your core.

For Tout, our unique advantage, our secret sauce if you will, comes from our ability to create clever user experiences and rapidly connect into various technology platforms to create the best e-mail client possible. This makes Engineering and User Experience the core of our company — and directly defines that types of people we should be bringing on initially.

And so, I set a short term of goal of hiring a Hacker and a Community Manager as the first two key hires for Tout.

What kind of person should you hire?

As a Technical Founder (who can also put on a sport jacket and do business development) — I absolutely CRINGE when I meet potential hires and they tell me “I only do front-end.” What do you mean you only do front-end? How did you draw that line and why did you do it?

When it comes to sifting and sorting through people, one of the biggest lessons I learned (from my last job) is to be able to tell the difference between a given person’s Values, Skills and Abilities.

Most companies focus on Skills when hiring, they focus on “C# developer with 3 years experience” or “CSS, XHTML and Javascript” and even resumes that read “PHP 4 LiFE, I’d never mess with Ruby.”

Let’s think about that for a second. Does that really make sense? The reality of the situation is that “Best Practices” come and go, Frameworks rise and die, and most importantly, Skills can easily be taught — PROVIDING — the person has the right Values and Abilities.

So, let’s establish our second Principle — Principle #2 — Don’t hire for Skills, focus on Values and Abilities.

Tout happens to be built on Ruby on Rails today. It is a platform that I have learned to love, but in the past 12 months, I’ve also built stuff on Python, PHP, .NET and even C++. If we are going to be building in a technology startup — you simply can’t afford to blindly support a single platform — you have to be open to different technologies, different languages — you essentially need to build an engineering team that is willing to be open minded and pick the right tool for the right job.

And so, as I defined who to hire, I definitely didn’t want the “Front End ninja” nor the “Backend rockstar” — I wanted the person that would pick the right tool for the job, and if he never used it, would figure out how to use it. This meant that the person had to have the abilities of a natural Engineer, a Hacker or a Tinkerer if you will — and it also had to be someone who values learning and trying new things.

A Values match is the most important thing

I think entire books should be written on how Values are the single most important thing when picking people to join your company. Skills can be taught, Abilities can be developed — but Values never change — it is the core of a person and it is what makes up that je ne sais quoi of successful teams.

There are different ways to identify a Values match between two people — whether it is the simple litmus test of “Would I want to grab a beer with the guy every week?” or something more involved like a detailed categorization of what you value in life (see my blog post about how I defined my own values) — it is probably the most important thing you need to figure out about yourself and your company.

Inspiration, Compensation and Incentivization

People are built differently. This means that what incentivizes and motivates me as a person can and will be very different from others. In addition to that, once you start to consider other factors such as location, married vs. single, kids, experience, etc — you start to realize that a blanket stock equity package with a base salary is neither fair nor enticing to every person.

With this realization, I established Principle #3 – Incentivize for all senses.

Having known Derek for a while, I knew he wanted to explore beyond his day job and really wanted to learn more about building great technology in a startup environment. So, when I initially approached him, my entire sell to him was the idea of joining Tout’s journey to build a great product. It was the opportunity to build a beautiful user experience, figure out unique new ways to integrate into APIs, and most importantly, really transform how people communicate using e-mail. Only after he was bought into the vision for the company and the ideas around how we were going to actualize that vision, did we talk details about salary and equity.

Both Derek and I are happy with the package we put together for him to join Tout and I’m really excited about the tremendous impact he is going to make on the product. However, I’m very cognizant about the fact that the next person I hire, which will most likely be a Community Manager, will require a completely different set of incentives and value propositions to be inspired to join the team. So remember, appeal to all the senses when you’re working to inspire someone to join your team, it is almost never about the money.

In Conclusion

Those are the three key principles I applied as I thought through and made the decision to make the first hire for Tout. This was not my first time hiring, nor was it the first time interviewing, but this certainly was the first time I literally built something and created a job.

Seasoned Entrepreneurs always talk about the emotional rollercoaster our journeys bring — emotions that take you to the highest of highs and the lowest of lows. Although I conceptually knew about these highs and lows, I think I came to truly realize how much of a high Entrepreneurship can bring — its no wonder so many serial Entrepreneurs exist in this world.

Calling someone up, looking him in the eye, and telling him to quit his steady and secure day job to join a startup was one of the highest highs I have ever experienced as an Entrepreneur or as a Human Being — ever. As I reflected on my train ride home, I thought to myself — “I created a job today.” — it felt amazing.

To set the context: Last year, I quit my day job and decided to experiment with a number of different product ideas. In the beginning of 2011, I reflected on the year of experimentation and shared my game plan for the year in a blog entry titled: I quit my job. Shipped 2 products. Launched a Services business with clients. Now what!?

As I said in my gameplan, there were a number of hard decisions I made in the beginning of the year. The most important decision being the one to focus on Tout and double down on it; even though my other products showed promise as well.

The Known Problems in my 2011 Plan

As I set the goal to build Tout to a revenue generating product, I saw two key impediments to actually achieving my goal:

• I was still relying on my Consulting business to pay my bills
• I am a one-man team spending 50% of my time (sometimes less) on building Tout

I flagged these as impediments but I was still willing to work through these without any drastic changes since Tout 2.0 had just launched and it was still more of a hunch that it would make a significant impact in increasing user retention, user growth and revenues. Additionally, I still had consulting contracts that would go on for at-least another two  months that I wanted to see through to the end anyway. I got these customers through my relationships, so the last thing I wanted to do was screw someone over.

Here’s whats happened in 2011 so far

• Tout passed 1,000 users
• We’re close to processing our 10,000th email (note that Tout doesn’t let you mass-email — so that makes 10,000 times that an actual person pressed the Send button on Tout)
• I’m starting to see regular upgrades to Premium — which means some real revenues for Tout
• I’m staring to see the marketing strategies (which were mere theories before) actually working
• I’m starting to see beyond the current version and well into the future where Tout can actually EVOLVE how we use email
• I’m working 80+ hours a week juggling my time between Consulting and Tout

Here’s what I’ve learned so far

• I’ve come to the realization that Consulting is a treadmill. There is very rarely a natural stopping point or transition — especially when it comes to 1-man teams. 37Signals and Harvest may have transitioned but thats about 2 companies out of the ~20 consulting companies and independent consultants that I’ve talked to or read up on.
• I had a ton of reluctance to even think about funding when I was working with theoretical ideas. But as soon as I started to see a product “click” — as soon as I started to deal with support requests with happy customers wanting more, and as soon as I started to see settlement reports in my Inbox…. my entire perspective changed. As soon as I saw traction, all of a sudden, I had ZERO issues looking an investor in the eye and asking for money — because all of a sudden, I was able to map out in my head how I’d not only get him 3x his money in a few years, that I’d also achieve my dream of building my own company and changing how the world communicates.

Ever since I was in 3rd grade, I knew that I wanted my own company. I never wanted to run a huge conglomerate or anything. I wanted a small outfit of about 10 extremely talented people that worked on a few products that truly changed the world. Most importantly, I wanted to be working on my vision and my ideas. Thats the vision I had since the 3rd grade, and part of that was the idea that I’d build up my business naturally with no one else’s help.

Now, I don’t know where I got the whole idea of doing it all myself — but as I grew older, as I worked in actual teams, as I managed people, and as I saw how relationships were just as important as ideas, and how a small braintrust of people can actually accomplish a hell of a lot more than one person or a large team, I slowly and begrudgingly started to morph my views of how I’d build my empire.

In Conclusion

Call it growing up. Call it turning 28. Call it getting wiser. I don’t care what you call it but what it comes down to is the fact that today, I’m ready. I’m ready to focus 100% of my time on Tout. I’m ready to build and evolve email through Tout. I’m ready to look an angel investor in eye and tell him or her: put your trust in me and my company, here is why we think we can deliver.

If you are an angel investor and would like to talk, just shoot me an email: tk@braintrust.co. I will immediately respond with a 2-pager PDF with an overview of myself and Tout, and then I will work with you to set up a time to talk/meet.

My goal is to close out this funding round before SXSW starts, so that I can focus my time there on evangelizing Tout and meeting awesome people to help build by team.

However, at the same time, its been wreaking havoc on my schedule.

Meetups can kill your productivity

All these little lunches, dinners and coffee meetups has been breaking my primary principle of not having anchors in my schedule, and pretty much been wreaking havoc on my creative process.

I learned last year that if I’m going to have a productive work day packed with creative output, I need to have little to no anchors in my schedule. This means no conference calls, appointments, or meetings. I found that all it takes is a simple 2pm conference call, and I end up counting down to 2pm for the entire morning and thinking about what I can quickly get done before than rather than embarking on solving a tough and meaty problem regardless of how long it will take.

I believe that if you’re going to be truly productive, and produce something actually creative, you need to eliminate any reason for you to be “counting down”  – in fact, you need to be in an environment where you’re just not thinking about time. You start when you start, and you stop working when the job is done. Period.

Moving all meetings to Tuesdays

And so, I’ve instituted a new policy called “Tuesdays work best.” Anytime I’m coordinating a meetup with someone, I always start with Tuesdays work best. For the month of January, I’ve been cramming all of my meetings, Skype calls, coffee/dinner/lunch meetups into action filled Tuesdays.

If this Tuesday is booked, that’s too bad, the next time we can get together is next Tuesday.

For all practical purposes, Tuesday is just the arbitrary day I picked. It just happens to work best for me because I can use Monday to catch up on everything that happened over the weekend, and then I can use Wed-Friday to get sheer amounts of work done feeding off the energy and inspiration I got from meeting all these interesting people on Tuesday.

In Conclusion

So far, this experiment has given amazing results. Not only is it easier to schedule, there are way less things for me to have to worry about re:travel, context switching, getting into the mood for meeting people, etc.

Do you have a  trick of scheduling? Do you have anchors on your schedule? Reflect on that and get back to me.

Note: Originally, I was going to do this as a 2-part post. I’ve changed my mind and consolidated it into one.

Major milestones of 2010:

1. I quit my day job through a principled decision making process
   Blog: How I made a principled decision to quit my six figure job
2. Launched Braintrust, a collaboration tool for small tight-knit groups of people
   Blog: Introducing Braintrust, my bootstrapped lean startup
3. Launched Tout, a web-app that helps you spread your message faster
   Blog: How I took my web-app to market in 3 days thanks to common services in the cloud
4. Established my umbrella company: Braintrust & Co. - my NYC-based design firm that believes in actuating change that leaves the world better than we found it, and does so by building awesome technology products. I also made the conscious decision to stay bootstrapped, and do consulting to pay the bills.
   Blog:  I want to be Bootstrapped, Profitable and Proud
   Link: Learn more about my consulting services
5. Started a Single Founder Mastermind Group — which eventually failed but connected me to some of the most amazing people including Andrew Wicklander from Ideal Project Group.
   Blog: I’m starting a Single Founder Mastermind Group
6. Built Main Street during NYC Startup Weekend, pitched it, and won a couple of prizes.
   
7. Launched Tout 2.0 – after nearly 700 users and 7,000 emails processed through the system.
8. Helped build and improve the user experience for NotaryCRM – it was a pleasure working with Paul Singh on this. I learned a tremendous amount about customer development and SEO.
9. Did some more consulting projects: Helped prototype and build a series of Internet Applications that will be debuting at a major industry show in Las Vegas in early 2011. Also, helped build a creative way to evaluate and view people’s competencies and capabilities for my previous employer

2010 year-end reflections

2010 proved to be an incredibly transformational year for me. I started the year with a standard Technologist job, and ended the year with owning my own company, a consulting business, and a couple of products in the market with real customers. Some days, I don’t even recognize my life and I have to remind myself that “this is not a movie…I’m living this!”

Concretely speaking, 2010 was a year of rapid prototyping.

1. My wife and I moved twice and lived in three different places this year. We finally feel at home at our new place on the UWS.
2. I experimented with a home-office, working out of coffee shops, and finally settled into to getting some office space down in SoHo with a couple of really close friends.
3. I took on a wide variety of consulting projects and experimented with hourly rates vs. retainers, project-based work vs. longer term arrangements, and enterprise clients vs. individuals.
4. I churned out rapid iterations of features and concepts for both Braintrust and Tout, and constantly measured metrics and talked to customers to gauge which idea/concept fit.

By the end of 2010, I ended up with a ton of data points, reflections and observations on the possible “design” for each of these various aspects of my life and my business. Armed with all these reflections, I believe I have a much better grasp of “what I want” and definitely a better grasp of “what I don’t want.” Similarly, for my products, I believe that I’ve got some solid theories that I can comfortably double down on to make these product visions a reality and a success.

In summary, I think the big theme for 2010 was “understanding the possibilities” and establishing a base foundation. I think 2011 is going to be about raw-and-powerful execution.

2011 Gameplan

Life

Fortunately, now that we’ve set up our home base in Manhattan, I feel that not only are we infinitely happier, it also feels like we’re standing on a strong foundation. Between our friends that are close by and the strong energetic startup community, I am 100% convinced that this is the place to be for us for the next few years. It’s an interesting thing — with a happy life, being able to focus on the business and make great things happen seems to become infinitely easier. Hopefully this will continue to trend upward through 2011.

Products Business

With the release of Tout 2.0 — getting this product to be profitable and successful will be my #1 priority. In 2010, I was able to figure out the ins-and-outs of rapidly developing products and features and got pretty good at it. In 2011, my focus is going to be to sharpen my marketing skills for these products and completing the last mile to make them successful. Things like SEO, content/article marketing, engaging in social media, drip campaigns, business development, and continued customer development are my primary focus and the skills I’m going to be sharpening+applying this year to make Tout, Braintrust and eventually Main Street a success.

One thing I noticed in 2010 is that since I tried to build as many repeatable systems as possible for development, creating Tout and Main Street after originally creating Braintrust became infinitely easier. For example, I didn’t have to re-create a login form, a forgot password mechanism, nor did I have to create another billing system. I tried to make these things as repeatable so that I could create and launch something like Tout over the course of a weekend.

Similarly, I’m going to try to build out similar repeatable processes/systems for marketing and all its components so that not only will I apply them to Tout initially, I’ll be able to quickly flip a switch and apply them to both Braintrust and Main Street when the time is right as well.

For 2010, my consulting business paid the bills. My intention for 2011 is that the products business takes that over and I continue to do consulting not to pay the bills but because I truly enjoy connecting with new teams and helping them prototype new and creative ideas.

Consulting Business

As I mentioned earlier, I tried a wide range of projects and consulting engagements in 2010. Through these different projects, products and types of organizations that I worked with, I developed a pretty good idea of the type of consulting work I like to do, where and how I can provide the most value, and most importantly, how much I should be charging.

It turns out that I provided the most value when a company had a vague idea of what they wanted to accomplish and needed someone to take on the goal and develop something “end-to-end” with everything from conceptualization, to design, to development to a game plan. The best way I found to describe this was rapid prototyping but with the idea that we’d still release something into the “real world” a the end of the project so that all our assumptions could be tested.

For 2011, I want to continue along the theme of providing end-to-end prototyping services, but I want to make a few tweaks. They are:

1. I want to reduce the number of clients or simultaneous projects to TWO at most. Ideally, this would be two clients that I establish a long-term relationship with through a retainer of some sort.
2. I take on projects that are less “internal facing” and more “external.” I want to build prototypes and test ideas for people/companies that are much like my own ideas — they must have the potential to actuate real change in this world and impact a large group of people. My initial research shows that this would probably mean connecting with some design agencies in New York City, but this is something I have to dig into a bit more.
3. I want to continue to prototype with web-based technologies, but I want to be able to work on projects that embrace more fo the established platforms on the web. This means that I want to do more projects that are in-line with Twitter-based, Facebook-based or Twilio-based applications.
4. I want to charge based on the value I provide, not the number of hours I work. One of my friends said it best. I’m a guy that can “build the shit out of just about any idea” — meaning, I can very rapidly take a vague goal/idea, establish a set of hypothesis, design a solution and bring it to life so that you can actually test it. This means a few things, but in the context of $$ this means that I do things very fast and at the same thing provide an incredible amount of value.

In order for my consulting business to be worthwhile, I want to be charging for the value and not for the # of hours. Maybe this is the entrepreneur in me speaking rather than the altruistic developer, but I do want to explore idea further in 2011.

I’m still finishing off the two major consulting projects form 2010 through January, but I will start actively looking for my TWO key clients for 2011 very soon. The Derek Sivers RFP looks very interesting right now, having him as a client and working on those projects would be AWESOME and is one of the leads on my list of people to approach.

Building out my team

Through 2010, I was basically a one man band. I did all of the conceptualization, design, development and marketing for all of my products (Braintrust, Tout and Main Street) and all of my clients for consulting.

I know very well that this has to change in 2011. So along with Products and Consulting, building out a real team that compensates for my weaknesses is going to be my 3rd and final priority for 2011. Ideally, I’m going to be building out a team that believes in the same things I believe in and we share the same values.

At the onset, this will probably start off as me setting up some contract positions to help get leverage on either my products business or consulting business. But hopefully, the contract work will turn into full-time positions. I’m 99% sure this won’t be about “finding a co-founder” — I’ve gotten very lucky with finding a life partner, I doubt I’m going to get lucky twice and find a great co-founder. At this point, my energies will be around filling up my team through employees and possibly phantom equity.

I fully recognize that I am severely limited due to that fact that I’m just one person — I want to fix that in 2011.

Things I’m still contemplating

The things I’ve outlined in my game plan are things that I’ve though about pretty hard  and am quite confident is the direction I want to go in. The game-plan is going to be all about raw-execution. There are a few things that I’m still unsure about and therefore will want to still mull over and experiment with.

Funding

I like the fact that I call the shots and can set the direction. However, I do wonder whether the consulting business is going to help or hurt the products business. There is something to be said about Focus, but it is also hard for me to ignore that my consulting business has been a fresh source of inspiration and ideas to fuel into my products business (and vice-versa ofcourse). I do better when I’m working on a couple of things rather than working on one single thing non-stop.

Nevertheless, I still wonder whether I should take on any seed funding to help move faster — especially for hiring people that I need to actualize my vision. I want to explore this a bit further in 2011 and understand what the right course of action is.

TechStars/YCombinator/etc.

I’ve gotten this once or twice. Not that many times, but it was suggested by people whose opinion I do trust and value and so I haven’t dismissed it. I don’t know whether joining one of these programs would just introduce more noise into my “raw-execution” plan or actually provide a ton of leverage.

Now that TechStars is setting up shop in NY, I’m started to consider this a bit more.

So, I’ll also be spending some time in early to mid 2011 to explore whether applying to TechStars or a similar program is a good move for me.

In Conclusion

So there you have it. That is my game plan for 2011. I’d love to hear thoughts, commends and feedback. Even more importantly, I’d love to get to know you if this type of thinking jives with you and if you’re on a similar path. Feel free to post a comment below, or just e-mail me directly.

Happy New Year.

For 2011, I want to take things to the next level.

It’s actually pretty complicated these days with Tumblr, Posterous, WordPress, Facebook, Twitter, LinkedIn and all the other ways to publish content. There is no doubt in my mind that producing good content and publishing it on the web is not only excellent for clarifying my own thought processes, but is also great for relationships and revenues (two things I care about deeply as a Startup Founder and Entrepreneur).

I’m writing this blog entry to share my thought process on how I’ll be thinking about publishing content and make sure I’m using the right tools and employing the right strategy.

#1 I want to continue to churn out good, timeless content

Most of the popular blogs out there today are by Entrepreneurs with huge exits under their belt. They churn out a ton of valuable content on how they’ve been-there-done-that-and-here’s-how-you-can-too. Well, I don’t have to offer. I’m still hustling and so I decided to write about the hustle, I decided to write about the journey of entrepreneurship as I crossed each exit and took each turn. To make sure  it appealed and was helpful, I made sure to always distill it into Principles. Principles are timeless, universal, and most importantly appeals to a wide range of people. For 2011, I’m going to continue to blog timeless content about my journey on this WordPress blog.

#2 I want to experiment with Video and Podcasting

Written word is great and has wide reach. However, after presenting this year at Startup Weekend and participating in a panel at BootstrapMD, I realized how much I love shouting out my ideas. It feels so much more dynamic and the rush is absolutely amazing. So in 2011, I want to experiment more with posting Videos (Gary Vaynerchuk style) and short quick thoughts. I’m also hopefully going to be starting up a Startup-related Podcast with a couple of good friends in 2011. Details on these will be coming soon.

I’ll be using my Tumblr account to post/share this kind of new media content. I’m using Tumblr for this because I consider it more of an “in-the-moment” thing, which I expect these videos, pictures and quick braindumps to be. Whereas, I expect  my blog to be more thought out content that spans a few hundred words and focuses on being timeless and about the meta.

Most importantly, I’m choosing Tumblr for this because I think the community aspect of the site is really cool and has a ton of potential to bolster my two big goals (remember? relationships and revenues).

#3 I want to embrace email

RSS readers are dead. Getting on the front page of Hacker News brings traffic spikes but not long term visitors. So with all of this timeless content I’ll be writing and with all these in-the-moment thoughts I’ll be putting into Tumblr, I want to be able to build a more dedicated following. I want to be able to distribute my content more effectively. To do this, I’ll be starting to develop an actual Mailing List.

In case you haven’t picked up on it yet, Mailing Lists and E-Mail in general is making a major comeback in our community, and realistically speaking has been the real money maker for all other “normal” people for quite some time now.

I’ll be building one master Mailing List where my blog readers, my customers, and people I have relationships with will be opting into. I’ll be segmenting the list as best as I can (based on Product, Relationship, etc). Once I have this set up, I’ll be taking the best performing new content  and will be sharing it with my mailing list monthly.

#4 I want to use Twitter/Facebook/LinkedIn primarily for Relationships and secondarily for Distribution

I signed up for Twitter back in 2006. Ever since Day 1, I always just assumed I “knew” how to use Twitter. I was wrong. Twitter works best when you stop copying and pasting the link to your product/blog-entry/whatever blindly and start focusing on all those little clues Twitter gives you on who you should be talking to.

I’ve found that Twitter works best when you follow up on the lists of people Twitter says is “similar to you” — when you follow up with people friends you think are awesome are talking to, and most importantly, when you “@” someone and say “Hey, what’re you working on?” instead of just shouting at them about how awesome you are.

So, in 2011, I’ll be doing more of this on Twitter, on Facebook and most importantly on LinkedIn.

#4a Do Not Write Off LinkedIn

Whatever you do, Do Not write off LinkedIn. LinkedIn is awesome because of their Groups section. In there, they have atleast 2 vibrant groups for any imaginable target audience you can think of. Go join those groups. Don’t just join and shout out your product, join and observe, join and have conversations, naturally, your awesome solution that can transform that target audience will surface and you’ll make a lot of money.

#4b Relationships first, Distribution second

My first focus will be on forging relationships and getting to know people on all these networks. Hopefully a byproduct of this will be a really large following. Once you have this, I’ll probably take advantage of that and share a few self-serving links here and there to promote myself/my product or a new blog entry. As long as my focus is relationships, I’m sure I won’t come off spammy and lose followers. And more importantly, since my focus is relationships, I’ll hopefully end up with followers that actually pay attention to my tweets.

#5 Easy-peasy CMS for each of my product’s domains

The last part of this content strategy is a very specific thing having to do with content related to my product’s target audience. I mentioned that this blog is the #1 traffic driver to each of my products. While thats great news for this blog, its actually pretty bad news when it comes to my products. As part of stepping up my Marketing game for my products, I’ll be churning out a ton of very specific content that will hopefully appeal to my product’s target audience. While these may take the form of blog entries, these will actually be highly specialized landing pages.

For example, Domainers happen to love Tout. They use it to pitch potential buyers on their domain inventory. Since I want to get more domainers, I’ll probably be publishing some content on Domaining best practices and a HOWTO page on how you can make more money with Domaining if you use Tout. I”ll be using a simple CMS for publishing this kind of content within my product’s domains.

So there you have it. That is my content strategy for 2011. What’s yours?

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.