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Categories: my thoughts.

It takes 3 years.

The end of 2013 marks roughly the three-year mark for my company. As I reflect on where we are today, from initial product, to an advisory round, to seed funding and then to raising our Series A in December 2013, one thing that I’ve always perceived from came true: it takes roughly 3 years for you to truly figure out if what you’re working on can be a business.

Once you hit that 3-year mark, and you’ve figured out a way to stay alive, some magical things do happen. Now, just to be clear, after the first 3, it’ll take you 2 to 7 more years after that to make it a wildly successful business; that is if you want to come along for the ride. But at least you feel just a tad bit like this guy.


In this blog post, I’ll share some reflections as I look back on 2013, my journey and the past 3 years.

First, here’s some context:

In case this is your first time, here’s some context:

  • Back in 2010, I made the decision to quit my 6-figure hedge fund job and start looking into building my own startup again (the first startup I co-founded was sold to Plaxo as we graduated college). I ended the year with a few different products and a consulting business. Yay, I was self-employed.
  • 2011 was one of the roughest years on my life as I moved from NY to California, started and incorporated the business, raised our advisory round, got featured on the likes of NY Times and went from a team of 1 (I’m a solo founder) to 4 and then back to 1 again. So, needless to say it took me until February until I actually got around to writing a reflecting on 2011 post.
  • 2012 I built out the team in San Francisco, built out the product, validated the market and went from ToutApp an email plugin to ToutApp, The Complete Sales Communications Platform. The biggest thing we did in 2012 was build a fantastic product and hyper-focused on our conversion rates from a self-serve free customer to a self-serve paid customer. We spent about $0 on marketing. This was the year we also made the tough decision to focus whole-heartedly on salespeople instead of email users in general. The year was chock full of learnings, and I shared all of it here.
  • 2013, we went into the year with a fantastic product, a market that was warming up. The problem was not every sales team knew about us. So 2013 became the year we continued to grow our self-serve business (and our conversion rates), but put a bigger emphasis on being louder and starting our sales team. This became the year of sales, the year of 1-year pre-paid deals, and the year of fundraising for our first institutional venture round, otherwise known as a Series A.

For the rest of this blog entry, as per my last few year-end entries, I’m going to focus on lessons learned and scars healed and earned.

It’s actually real hard.

I’ll be honest right over here. It all sounds really nice, neat and clean when laid out in a bulleted list like the one you see above. Year 1: Build product, Year 2: Charge, Year 3: Sell; Raise Right? The last three years have been quite possible the three hardest and most grueling years of my life. And yet, there is some gene inside of me, some sort of programming in my head, or some sort of carrot (that I can’t identify quite yet) being dangled in front of me, that makes me keep going on. Even when a company I hugely respect gave us a compelling offering to buy us in 2013.

I think we all know that its hard, and a certain percentage of us do it anyway, and go on to survive in varying extents. There are also some in that budget that build businesses worth $1b to $3b in an 18-month period. I call this bucket of people “true believers.”

As I’ve come to meet more and more startup founders and CEOs, I’ve come to realize that no one in this group does it (and survives) because they do it for the money. It’s only the ones that have some sort of higher purpose that drives them, a chip in the shoulder, or a deep passion for a specific thing, those are the ones that make it to a 3-year point where you only come to realize, well — this may work, let’s double down more.

3 Years = This MAY work

For any business that you start, I can say more confidently than ever before it is going to take you 3 Years to figure out if this may work. Meaning, for anything < 3 years, you will know nothing more than small wiggles of hope. In fact, for the first three years, you’re primarily going to be in heads down more.

Expect to get your first point of true validation and proof that this may work for real at the 3-year mark when you’ve done enough things, had enough persistence, and focused enough to have real customers, real revenues, real investor validation, and real people as you look around the room of a committed team that will go to the ends of the earth for the cause (real people who you didn’t know > 1 year ago).

Don’t get me wrong, at this 3-year mark, things do start to come together beautifully. You have a ton of conviction around the business, hiring becomes a bit easier because a number of proof points exist around the business, and while you have to approach the coming years with vigor, optimism and gumption, you also have to keep in the back of your mind and be hyper realistic — this may work, but there’s hard work ahead.


No, I’m not talking about the 1%. I’m talking the .1%.

I was in a room with 30 CEOs the other day as part of the SigmaWest CEO Summit. One of the sessions was an analysis piece on the investment trends around the VC industry.  I’ll probably never forget this presentation, or more specifically, the specific moment when a slide showed some math around the general success of a startup entrepreneur.

He said, “Can anyone guess what percentage of people attempting to raise money for a business end up raising?”

Answer: 0.5% (Half of a percent)

Then he said, “Ballpark… what % of startup founders that do raise end up with stock that ends up being worth something real?”

Answer: 20% (Ballpark)

Now, I’m no stats genius (feeling a little self-conscious now because I hope I did the math right here), but I went on to calculate the general ballpark probability of a startup founder raising money and then making money from the venture.

.005 x .2 = .001 = .1%

Needless to say, here I was, three years in on ToutApp, four years in on being self-employed and on the journey of being a startup founder, and for the first time, a banker was explaining to me the true math around starting a venture-backed business. The crazy part? It wasn’t a moment of holy shit, stop this madness; the math is insane. It was a moment of: OK… Hmm. Keep going.

Why we really do this and keep doing it: the people

In 2013, I figured our the real reasons the likes of Bill Gates, Mark Zuckerberg, Elon Musk, and of course Steve Jobs kept going to build corporate dynasties that went on to or will last 10+ years. Having studied all of them, having watched all their interviews, their books/biographies and yes, having watched The Social Network (joking), we can all see that these guys were machines that were driven by something, not exactly sure what, but I think after three years of doing this and watching my team grow and my business grow, I actually finally figured out what that thing is that drives startup founders.

It’s the people.

Through 2013, I had the pleasure of growing the team, hiring amazing individuals, seeing existing team members hit their 1-year marks and celebrate. I even got to meet countless customers and Tout evangelists. It’s a seriously amazing feeling when you meet someone you don’t know and they say “Hey! I use ToutApp! Love it. What do you do there?” … “I’m the founder. What do you love about it?!”

And as I reflect back on all of those moments, I can say that the single most important reason I do what I do and I fight the good fight is because of the people that we have who believe in what we are doing.

It’s funny that this is how it works. At first  it’s just you, doing this one crazy thing. And then there’s one more, then two more, and then eventually there’s a group, then a clan, a village, and then you hope eventually there is a nation and a whole eco-system.

The true essence of entrepreneurship seems to be the act of starting something from nothing for one’s self and then setting out to find as many people as possible to join your cause so that you can make it not just a cause of yours but a cause for all.

In 2013, I truly saw Tout Nation come to life. And its the single thing that kept me going, even on the hard days. If you want to see a visual depiction of what it feels like to be an entrepreneur, check out my blog entry on it here.

And… at one interesting moment, without even realizing, it switches from being about yourself to being about them. And you stop working hard for yourself and you start working hard because you want to protect your people, you want to grow the beliefs that you all uphold, and you want everyone that is part of your nation to thrive.

On Success, 300% Revenue Growth

Through 2013, a huge number of things came together beautifully around the business. The sales team started to hum, we started closing $40,000 1-year deals, and our inbound lead volumes went up to a point where we had to dedicate time just for lead qualification and nurturing!

Not only did our overall revenues grow by 300% in 2013, our self-serve part of the business, something we didn’t put as much focus on in 2013, grew beautifully as well. It was magic.

The customers were great, the product was starting to mature, we saw a strong following around our brand. It was official, we had become a tribe.

How do we go from a tribe to a nation?

In 2013, it started to become evident that we had a tribe, a following, a core group that believed and pretty soon we’d have to strive to become a nation and then a real eco-system to take the business to the next level.

I’m all about running a lean business, and I’ll be honest, I’ve scoffed many times at startups that raised outrageous rounds with seemingly small ideas or businesses. But as I sat there with a spreadsheet and crunched the numbers on what it’d truly take to grow the business faster, to win in the market, and to continue to innovate on the product, I slowly came to the understanding that we needed more money to grow.

In an interesting way, while going through that exercise, I finally figured out through my own model how a cash-infusion into the business can accelerate the bottom line growth. For once, I was thinking about raising a Series A NOT because it was “just the thing to do” but instead, it was “the logical next step.”

And so as our sales process started to mature, as our marketing become a repeatable system, and our product stabilized, I shifted my focus to thinking about further capitalizing the business and figuring out what to do next. Fortunately for us, through one of our largest enterprise customers, we got connected to Greg from SigmaWest, and by the end of the year, we went on to raise our $3.35m Series A.

On VCs, the ones that leave you in the conference room at the end of the meeting.

Through our fundraising process, I got the pleasure (and displeasure) of meeting about 20 VCs in total. While there are a ton of tools, websites, and relationship networks out there that helped me find out who would be the right person and firm to partner with, I did keep meticulous notes on my interactions with each of them. Fundraising is inherently a sales process, and so I actually kept track of it all through a SpreadsheetCRM sheet.

As I went through the process, I rated each of the partners I met with on different factors, just for my own notes. And so, after our round closed, as I looked through my notes and reflected on my interactions, there was ONE common theme I found in my barrage of notes and ratings.

The VCs that walked me out to the lobby or the door at the end of our pitch meetings turned out to co-relate with the best rated and successful VCs in the Valley. The ones that left me to my own devices at the end of our meetings and just went back to his office, turned out to be the less successful ones.

(In case you were wondering, Greg walked me out to the street and had an additional conversation after our meeting, so he got extra points in my book).

People = Everything

At the end of the day, the real business we’re in is the people we choose to enter into our lives and spend time with. Period. Whether it is hiring employees, partnering with a VC firm, selling to a particular demographic of customers, or building an eco-system, we are all in the people business.

Through firings, hirings, good experiences and bad, the one thing that I’ve come out with in 2013 is that the people make the biggest difference in all aspects of your life. Sure, someone might short  change you, or screw you over, or may fund your competitor after pretending to want to invest in you, without even a heads-up phone call, that’s all fine. Because what I’ve learned is… as long as you maintain your integrity, pick the right people, and deliver unparalleled value: the rest takes care of itself, the right people flock to you and you grow. Karma.

So while my metric for gauging VCs may come off as silly, think about it hard and make sure you have metrics in place to gauge the people you’re choosing to spend your life (both professionally and socially) with.

If you’re thinking of starting…

As I close out my thoughts, I did want to reiterate one thing. Although the last three has been hard and grueling, although I’ve had sleepless nights, tough conversations, and challenges, and even with the 0.01% likelihood, and even with the possibilities of failure, I still highly recommend starting a startup or better yet, joining a startup.

For as low as the lows have been, the highs of closing an Enterprise deal, of walking into an office where EVERY person including the engineer is on the phone with a customer, to meet with smart people who validate your business and understand your vision, and even to meet with personal heroes because they want to spend an hour hearing about the business you’ve built — all of those highs, have been the highest of highs of my life — and I wouldn’t exchange it for anything else. Nothing.

So if you’re thinking of doing that startup, or joining that risky early stage company that has a small room in a co-working space, DO IT. At the very worst case scenario, you’ll come out of it with real lessons learned and some friendships that you’ll hold dearly for the rest of your life.


As I look forward to 2014, and as I plan out my business, the biggest hope that I have is that we continue to be surrounded with fantastic, smart, and passionate people who join our team, become our customers, and partner with us. In 2014, it is my hope that we grow from a tribe to a nation and that we flourish and that we crush those that try to get in our way.

We’re all seriously excited about making sure every Sales Team uses ToutApp.

Email me your thoughts: tk at toutapp dot com.

Categories: entrepreneurship, my thoughts.

This is great. But I’m not coming back to your awesome web-app after signing up.

Almost every other day in Hacker News, I find the announcement about an awesome new web-app that potentially solves a critical problem in my day to day life. When it comes to the web, we’ve gotten very good about landing pages that clearly communicate values and absolutely frictionless signups that lets me get into the app with the click of a button.

I’ll Sign Up. I Probably Won’t Be Back

I sign up, go through their new user experience, take a look at their snazzy and beautiful interface and then I move on. Regardless of how many new applications I try, in reality, the actual applications I log into on a daily basis are the ones that are tabbed in my browser:

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Thats right. Aside from Gmail, GCal, ToutApp and Asana, there are literally no other web-apps I log onto. I started to realize this more and more lately as I try out new applications and web properties. I’ll sign up, I’ll look around, but then I get that sinking feeling as I “zoom out” from that browser window and realize all my other open tabs, my calendar alert for my next meeting or conference call, or better yet, my overflowing Inbox demanding my attention.

This is great. But I’m not coming back to your awesome web-app.

Coming Back = Changing My Daily Habits

Truth is, the caliber of web-apps I come across today all solve really great problems I have, but very few ever cross into the threshold where I change my daily habits of which web applications I’ll re-open after I reboot my computer. Could it be that web properties are becoming staples in our daily lives much like our de-facto coffee shop, supermarket or butcher?

5 Ways You Can Get Me To Come Back

Relax, all is not lost though. Over the past year, we’ve spent a tremendous amount of time working on how to make sure a new ToutApp user comes back. Here are a few things you can do and in fact I wish more awesome web-apps did to make sure that I come back… Because, in all seriousness, I do want to be back, but I probably won’t remember.

#1 – Don’t expect me to come back. Figure out a way to plug into where I already hang out.

This is the most sure fire way of getting me to come back. Just don’t expect me to. So instead, send me an email a few days later reminding me of the value proposition, teach me something on how I can better solve my problem and gently pull me back in.

#2 – Retarget Me

I’m a huge fan of both ReTargeter and Adroll. Their solution lets you cookie your new users and then re-target them with gentle advertisements across the web to pull them back into your site. Just be careful with this. You’ll want to track the lifecycle of the customer and retarget only during the first week or two and then stop — otherwise it just gets annoying.

#3 – Call Me

If you’re a serious B2B business then you should be asking for my phone number during sign up. If I’m a valuable enough lead to you, then you should actually hire a Happiness Officer to call me and ask me how they can help me solve problem X. Look, I signed up, I was interested, but I was probably too busy to figure it all out, so help me out will ya?

#4 – Integrate into my life, don’t expect me to integrate with you

Look, you’re great and all. However, unless you’re deeply integrated into my staples (Email, Calendar, Word Processor) I’m probably going to forget about you and more importantly you’re probably never going to be important enough to me. So if you really want me to come back, integrate into my life and stop expecting me to integrate into yours.

#5 – Be ridiculously bad ass

Lastly, if you don’t want to do any of the above, you just need to take me from Sign Up all the way to your core “A-HA!” moment right within the first 2 minutes and once you make me feel that “A-HA!” moment you have to be so insanely badass that I’ll have no other choice but to integrate my life into you. An example of this would be Facebook or Twitter.

In Conclusion

We’ve figured out a lot of things on the web when it comes to conversions and activations. But retention is tough. Follow the basic ideas above and you may get me to come back to your awesome new web-app. But just to be clear, unless you’re ridiculously bad ass, I probably won’t stay for long even if I do. Thats why SaaS businesses are hard but when you get it right they are incredibly lucrative.

Categories: Principles.

20 Years


Today marks the 20th Anniversary of when my parents decided to immigrate to the United States of America.

I was 9.89 at the time. My brother was 7.

My Mom and Dad were in their early 40s and they embarked on a journey of not only reinventing their own lives, but their entire livelihood and the trajectory of how my little brother and I would grow up.

Today as I reflect on the past 20 years here, I can’t help but be thankful for all the benefits, advantages and opportunities that this great country has provided for me. My parents changed every aspect of their lives so I could live in a city like New York, so I could go to an amazing public school like Townsend Harris and an institution like RPI, and most importantly, they brought me to a place close to Silicon Valley where I could push my passion for technology well beyond my wildest dreams.

As a country, we face a tremendous number of challenges in these changing times. Same sex marriage, women’s rights, gun control and even immigration reform the agenda is endless. However, let’s not forget that it is far better to live on a land where such open dialogue and debate is happening vs a place where nothing is.

Categories: my thoughts.

Rule #1: Show Up


Say you want to start your own company. Or perhaps make a career change. Maybe you want to approach your boss about that that manager position thats open in your department.

These days, there are countless resources available at your disposal to help you think through this process and take the leap. There are user groups and weekend events entirely dedicated to jumpstarting your entrepreneurial career, tons of career coaches, and countless books and classes on the subject. Conferences are particularly great to get the right vibe going and get riled up to take that leap.

However, most people don’t.

Most people don’t leave that shitty job.

Most people don’t pursue that idea in a real way.

Most people don’t step up.

Most people just don’t show up.

Interestingly enough, no-shows are not only rampant in career related events, its also widely rampant in personal endeavors as well.

Here’s a picture of my Mom and Dad at roughly the same age Mahrin and I are now. Here’s a picture of us for comparison. What’s the difference? At that age, my Mom and Dad not only already had me, they were already thinking about having my brother. They showed up.


My Dad was running a successful business in Bangladesh, my Mom was playing full time Mom and part time school teacher, and they both were just making it happen.

The interesting thing here is, they had less.

My Dad had 10x less resources around starting a business back then in a country where entrepreneurship is still not encouraged. They both had 30x less resources around how to raise a kid and grow a family back then.

This is where Rule #1 comes in and truly exemplifies itself. There is never a perfect storm and perfect time to take that next step. There will only be troughs and peaks of imperfection and its up to us to capitalize on that and just step up, and show up. It is a universal truth that for things that we find daunting and hard, there has been countless people that has done it before us with less.

I think in today’s fast paced information packed society, when we do think about taking the next leap we get so inundated with the pitfalls and watch outs and the ins and outs, we forget Rule #1: Show Up.

Don’t wait for only that perfect moment. Start by just showing up.

Just show up.

Categories: my thoughts.

You can do that? Why you should be a contrarian on the small things for getting big results.

I went to Bikram Yoga today. Yes, thats the one where you sit in an 80 degree room and do Yoga. As I set up my mat, lay down my towel, and sat awkwardly for the instructor to start the class, I looked over to my right and saw someone laying on their mat in deep slumber completely relaxed, completely calm, waiting for the class to begin.


“You can do that?” I thought.

Quickly I realized, why of course. Why couldn’t you lay comfortably and wait instead of doing what most of us were doing –  sitting in some awkward uneasy position awaiting instructions.

Unfortunately, unless you’re constantly ON and constantly thinking critically, most of our decisions and designs are geared to mimic what “most others” are doing. Rarely do we stop and say well, “How should this work?” or “What do I want?” or surely there’s a better way unless its something absolutely core.

Some think about how to be different for the big glaring things. Most don’t ever try to think differently for the smaller things.

However, companies and individuals that think critically about the smallest of things are the ones that truly innovate and make a huge impact.

Be a contrarian, not on the big things, but on the small things. Not for the sake for being a contrarian, but for the sake of finding a better way.

Categories: my thoughts.

Reflecting on 3-Years as a Startup Founder: Strength, Persistence and Fear

About 3 years ago (2010), I made a decision to quit my hedge fund job and start upon a journey to build my own company: Tout. This blog entry reflects on the past three years and gives you an update on where I stand today.


By the end of 2010, I had already quit my job. Shipped 2 products. Launched a Services business with clients. Now what!?.

As 2010 came to an end, Tout the most promising of the ideas I had been working on had acquired nearly a thousand users and even started generating revenues from day 2 of launching. Seems tiny in retrospect but for back then it was amazing. All I really had was a glimmer of an idea and a bit of market validation.

At that time, it was still just me. I was the Founder, Engineer, Designer, Marketer and Customer Support. But, beyond just me, others took a look and could tell there was something there. It was quite a bit of a contrarian view at the time. Instead of betting against email and trying to make everything “social”, even then, Tout was about making Email work better and believing that Email/Digital 1-to-1 communications would grow in usage and the tools we use to communicate would need to evolve.


In 2011, I decided to drop everything else and concentrate all of my efforts on building Tout as a real company.

With the rise of convertible notes, accelerator programs and the general fundraising climate of 2011, I decided to switch from a bootstrapped startup and raise money for Tout.

Through 2011, I joined the 500 Startups Accelerator Program, built out a team of some seriously amazing people, Raised a seed round of nearly $800k from the likes of Esther Dyson, Eric Ries, Dave McClure and others, and built out ToutApp to what I like to call “Version 1.0″

Although I had made it a tradition to write a “Year In Review” post since 2009 or so, I ended up not writing one at the end of 2011. I had done so much, Tout had grown so much, and yet I felt no sense of finality as December rolled around.

2011 was Tout’s Foundational Year

Through the course of 2011, we grew our user base, we grew the footprint of our product, we grew our revenues. We talked to customers and got a core understanding of the problems we were solving. Looking back, it was a foundational year that every startup with a long enough view needs to have and needs to go through. However, as the end of 2011 rolled around, things didn’t feel all that great.

After spending the summer in California, it became evident that I needed to stay there instead of going back to New York to maximize the outcomes around the business. However, with a distributed team stemming from New York, Indiana and California, merging everyone into one place would be downright impossible.

Tout was my baby. Moving to California felt like a no-brainer to me. Fortunately, my wife was incredibly supportive as well and didn’t give moving a second thought either. However, it wasn’t the same case for the rest of the team. They weren’t founders. They had families, friends, lives that they couldn’t necessarily uproot. And so, Tout came back to being just me.

As the end of 2011 rolled around, we did a holiday promotion called “Your 2011 Email Year In Review.” Through the course of the holidays, we signed on 20,000 users, and got featured on The New York Times, Mashable, TechCrunch, and countless other publications. The servers crashed and burned, but somehow we got through it. We acquired users, converted to revenue and got our name out there.

No one knew it was all being done by a now-1-person company. Not even the New York Times.

It was a serious conundrum that even I couldn’t believe. As our transition to San Francisco brought down our actual team count to 1, our user base continued to grow. Our revenues continued to grow. And since I was already used to being the one-man-show, the product continued to get better.

2012 – Tout Grows Up

So as 2011 ended, I stayed calm and carried on; however, I couldn’t find the mindset to write down a “Reflecting on 2011″ blog post because of the utter lack of finality or at least one worth writing about.

As 2012 started, it became clearer than ever that Tout was onto something important. Even if my faith or my beliefs faltered for as second, our amazing customers and community constantly reminded us how Tout made a serious impact on their day to day which they would more than happily pay $30/month for. And so while in retrospect January was probably an insane month for me, at the time I felt like a surgeon standing in front of a dying patient with steady hands and a plan on what needed to be done.

As January rolled into February and onward through Q1 of 2012, we closed the remainder of our seed round with Founder Collective and a few others. What we needed to build for Tout to take the business to the next level was clear, and so I continued to set out to establish ourselves in San Francisco and make key hires in Support, Engineering, Sales and Marketing as we continued to grow our paid customer base.

As I look back at 2012, I can wholeheartedly say that its been the most intense, most stressful, most amazing, most balanced year of my life that I have ever lived. In other words, it has been the quintessential definition of an Entrepreneurs life at its extreme.

2012′s Focus Was on Product

Through the course of 2012, we’ve achieved what we call “full coverage” here at Tout meaning, we’re now fully and deeply integrated into Gmail, Outlook, Salesforce, iPhone, and all major web browsers. We’ve developed our on boarding, training, support, sales and marketing programs and we’ve figured out ways to predictively convert new customers to paying customers to retained customers in a systematic way.

We completely rebuilt Tout’s GUI from the ground up and expanded the platform well beyond simple Email Templates which is how Tout got its start back in 2010.

And most importantly, while I always referred to Tout as “we” even when it was just me, through 2012 we grew Tout’s team to make sure all key areas of our business including Engineering, Customer Happiness, Training, Marketing and Sales had smart individuals to think through a design and operate it like a well oiled and beautiful machine.

Don’t get me wrong. We’re still tiny, there’s only 6 of us. However, the ratios around the business and the amount we get done with just 6 people, never cease to astound me. As 2012 comes to an end, we have more computer screens than we have employees. We are integrated into more platforms than we have employees. While most SaaS companies enjoy < 1% of their user base as paying users, we have nearly 3% of our user base paying us for our B2B offering. And of course there’s my favorite, nearly 8% of users signing up every week will end up paying us with their credit card.

2012 – I Grew Up as a Startup CEO

While the end-state of 2012 feel a heck of a lot better than 2011, I’d be doing all of you a disservice if I wasn’t honest about exactly how hard, tiring and painful this year has been. There is absolutely nothing of certainty when you’re doing a startup. And for the better part of this year, I’ve slept very little at night because of that.

When you’re just starting out, like I was back in 2010 and through a good part of 2011, you have absolutely nothing. Having absolutely nothing is one of the best blessings one could ironically ask for. Having absolutely nothing means you’ve no reason to fear anything because you’ve got nothing to lose. The smart ones through this period go through a period of amazing wonderment trying different things, taking bigger and bigger risks, and doing anything and everything possible to make something to replace the nothing.

Once things start to click. Once that first big customers comes on. Once that really great investor comes on board. Once you win that really great deal it all changes. Its the dream of every startup founder, some call it product market fit, some warn of it as “be careful what you wish for.” Once you have something its a whole different game you start to play. Once you have something its no longer about doing anything and everything and seeing what sticks, it becomes a careful game of management.

Management is a term we think we understand, but until you really stop and think deeply about it, especially as a Startup CEO you don’t truly understand the breadth and weight of the responsibility.

2012 – On Not Sleeping At Night

As 2012 came to be and things started to progress with our product, our market, and our team, I entered into a mental state for the majority of this year that I believe has no real name or categorization but can only be attributed to serving in the role of Startup CEO.

The first thing that happens in this state is related to sleep. Sleep becomes redefined. It’s no longer “go to bed because you can call it a day” it’s more of a “well I guess now is the time to sleep but all you can do is lay awake and stare while your mind processes thinks and reevaluates scenarios at light speed.”

You start to incessantly check Twitter/LinkedIN/FB in the morning only to confirm that the darlings of Silicon Valley are still indeed killing it and you get another fire lit under you just so you can try and “catch up” today.

God forbid you do get featured profiled or become the darling now you work 10x harder than your already 100x pace because behind the scenes things still feel like you’re running an ugly dirty sausage factory.

Although you conceptually realize that this job is all about keeping your head in check you still struggle to deal with the raw emotions of it all.

2012, I Know Why We Work So Many Hours

The interesting thing is the emotions rarely come into play during office hours. Between the hours of 9 and 7 (on average) when I was actually in the office, it was like being in a symphony orchestra. You focus on the most important things, you code, you talk, you brainstorm, you fix problems, you DO things because then at least you feel like you’re doing something about the fear of failure you’re doing what you need to so you can carry things forward to the next level.

Maybe this is why we work so many hours. Not because we are so damn productive at our 80th hour of the week, its more because not working is just so damn unbearable.

Speaking of non-work-hours. At some point you probably signed up for a real life with real friends and real relationships. Through 2012, I had to either make a conscious decision to cut off those ties and make my company my life or decide to pursue that elusive “work-life” balance.

Fuck work life balance. You never actually achieve balance because you can’t stop thinking about it. But – you still go to the birthday parties, double dates, you drive your house guests to napa and you spend Sunday afternoons grocery shopping.

You talk you laugh but inevitable you get a little quiet. A little reserved. Truth is you’re just going through the motions. You’re not really there. You’re numb.

Inevitably they’ll ask how’s the company you put on your PR face and give the byte sized clips. Worst case – you say “great!” Even worse, they happen to mention the name of a competitor. Thats it. You can now clear out the rest of your night schedule at that point and sign yourself up for at least one more restless night.

2012, Mondays, Days, The Concept of a “Day”

And so when Monday rolls around you’re just exhausted from trying to be normal and escape numbness but now that Monday is here all you really want is a day alone where you can just hear yourself think. But that’s out the window because there’s a slew of customers, employees, investors etc roaring to go needing things doing things and so you just jump in.

Thats fine though, give it 10 minutes into the office, and then you’re back into the symphony orchestra again. It doesn’t matter how tired you are. You don’t even remember it anymore at this point. You’re in the zone. You love it.

At the end of your day your loving wife might ask you how your day went. She cares. She deeply cares and she wants to relate. Except to you it doesn’t feel like a “Day” it feels like you started your day last Thursday and haven’t skipped a beat and you’re already planning tomorrow and tinkling about next week and so your exhausted overworked mind literally has no synthesis on how TODAY went because for all practical purposes there is no today and no tomorrow there is just ON and OFF and you haven’t turned if OFF for god knows how long and you won’t till you reach your goal.

None of these things are good or bad. This is no ones fault except your own. Its my own fault. I signed up for this. Remember? I quit that 6 figure job so I could have this instead.

2012 – Goals

Goals. Thats a funny word in this stage of the company. We have milestones, weekly goals and you hit them or you were aggressive in goal setting and maybe you don’t. In the back of your mind though, you know very well that all of this is arbitrary. The only goal there really is the only one that really matters is when you’re “wildly successful.”

By now you’ll have forgotten how many times you pushed back that goal post. You won the little battles and you just kept pushing forward because every win felt like a small win and you felt like there was always something more and so you forged ahead because that’s the right thing to do and so at this point what is the goal really? Wild success. Killing it. IPO. Acquisition. Surviving.

2012 and My Partner In Crime

“Are you still enjoying this?” When my wife sees that I’m stressed out, she always asks me that. Its her way of reminding me where I’ve been, the decisions I’ve made, and reflecting on where I am. I love her for it. In fact, while I made it a policy to not let my wife work within Tout, I’m not exactly sure where I’d be if she wasn’t around. Through the course of 2012, she made sure I kept by Gout in check, she made sure I went to the gym 3 times a week even if it meant being the bad guy and nagging at me. She made sure breakfast and coffee was ready and a nutritious lunch and dinner was at arms reach. There has been two big empires I’ve been busy building through 2012, one is Tout and the other is our family with my wife. And to be honest, because of her and her support and her love, I have unparalleled faith in the success of both empires.

I’m Still Loving This

From a well paying desk job to nothing to something to now. Today, Tout stands strong as the most complete Sales Communications Platform. Through 2012, we’ve come together as a seriously amazing and fun team, we’ve brought on customers that are using our platform to do amazing things, and I can’t help but shed a tear when I watch this year-end video we put together featuring the state of Tout and the team.


We’ve worked hard over the past 3 years and now we have a platform that is unparalleled. We’re switching from being inward and purely customer focused to expand into aggressive Sales and Marketing. This ain’t vaporware, this is a real throughly tested and deeply thought through solution now. We’re all seriously excited about making sure every Sales Team uses ToutApp.

Yes its hard. But this is Startup life.

Email me your thoughts: tk at toutapp dot com.

Categories: my thoughts.

Jab, Punch, Jab — the Startup Mantra

Recently, I took up Boxing. Not the Taebo Cardio punch in the air boxing, also not the get into a ring and fight someone boxing; a middle ground crazy workout three times a week for an hour including a punching bag and spar in the ring boxing.

One of the biggest things I like to do is to look for patterns in life and draw them to core principles that weave together everything you do in your life. Core principes are powerful that way because no matter the situation, you can still apply them to solve problems.

My boxing instructor told me, if there is one thing I want you to learn in this class, its the “Jab, Punch Jab.” Meaning, if in the real world you ever have to defend yourself, you want to be able to deliver a powerful Jab, Punch and then a Jab and then get the fuck out of that situation.

For those of you that never really looked into boxing, a Jab is a quick pump of your left hand (for righties) that go right into the face. Its quick, fast, and you take a Jab with a quick step forward and then return to your position to re-asses the situation.

Once you jab, and you hit, you want to go for a full punch. A punch is a where you put in your whole body weight, let out a serious breath and use your right foot to “squash the bug” — lunge a bit forward and deliver a seriously strong blow to your opponent with your right hand.

And finally, while your opponent is literally flabbergasted with the Jab and the Punch, you want to finish the combination with another Jab. Except this time around, that same simple jab will have an even more profound blow building on the previous two blows you dealt to the opponent.

Thats the Jab, Punch, Jab.

I’ve found the same applies to Startups in terms of a core principle.

The most successful startup founders out there, in my opinion, start with a series of quick jabs to feel out different ideas. They take quick easy hits into problems they think they can solve. Some end up going into empty air, some end up being a partial hit, and then one ends up being a direct hit.

Most thriving startup founders today kept jabbing when they hit thin air, and as soon as they hit the bullseye on that first jab, capitalized on it and went for the punch — either through raising funding, starting the startup, expanding the product — but all in the sense of building on the jab and doing the harder work to solve the deeper problem.

And finally, they followed the punch with an even quicker jab – a jab that built on the punch, was just as effortless as the first jab, but had a seriously more profound effect because it built on the initial jab and the hard work of the punch.

So regardless of whether you’re looking to start a startup, in the midst of Heads Down Mode, or are just about to come out of a period where your team has been hard at work building some seriously defensible technology, remember the Jab, Punch, Jab principle.

If you’re just staring out, keep jabbing till you make a hit

If you just made that first jab and made a hit, figure out that seriously hard problem that needs to be solved and put in the hard work to go in for the punch. The punch takes time, takes effort, takes discipline, and is where most startups fail — but if you pull through then you deal a serious blow to your “opponent” and can follow up with a serious of jabs and combinations that have far deeper impact but are way more effortless for you than it would have been otherwise.

Once you’ve put in the hard work, look to finish out the combo with another Jab, a jab that builds on the hard work of the punch, a Jab that builds on what you’ve done so far, is just as effortless as the first, but would’ve been impossible to deliver without the punch, and delivers a profound impact.

Rinse, Repeat. Build. Win.

Jab, Punch, Jab.

Categories: entrepreneurship, my thoughts, Principles.

Bumbling and Awareness During Heads Down Mode

My last blog entry about heads down mode for Startup Founders seems to have struck a bit of a chord. So, in spirit of continuing the topic, I decided to write out some thoughts around how I bumbled around at first and then eventually got into a cadence of effectively staying organized through a seemingly endless and dark period that I call “heads down mode.”


Although this now pretty-standard graph outlines different stages that your company goes through, I don’t think it quite captures the stages that you yourself as the founder go through in your own head. As I reflected on the past year or so, I’ve been able to break down this period of heads down mode into two distinct mindsets: the bumbling period and the awareness period.

The Bumbling Period

One of the biggest points of discussion that stuck out in my mind about the heads down mode thread was that this is the period when tons of startups die. This is the period where if you’re not careful, resilient, and organized, you’ll basically lose sight of time, lose interest, or even worse, run out of money and fail to get to the promised land.

Obviously, when you’re deep in it, its hard to take a step back and realize where you are and what the pitfalls to watch out for are. The Lean Startup methodology teaches us build -> measure -> learn at all times, and to look at meaningful metrics at all times, but doesn’t speak much in terms of having the right mindset, outlook or basic organization around running and building a team/business.

In the earlier months of ToutApp once we raised funding, my first inclination was to push down hard on the gas pedal. We rented an apartment in Mountain View, and pretty much started working right after getting out of bed till late at night. This went on for 3 months. We had To-Do lists, we kept an eye on our metrics to make sure we were seeing incremental improvements, but there was just so much to do, all we knew was that we were behind and we needed to push as hard as possible in time for Demo Day so we can make things go “boom.”

The Awareness Period

Eventually you realize, this is not a sprint. Sure you can get lucky and strike gold and at the end of your sprint you can win Gold by tapping onto the perfect distribution channel and the perfect viral loop — but those things are 1) hard to come by 2) usually not a strong foundational thing (e.g. Turntable — which encountered this phenomenon during the same summer we started ToutApp).

Eventually, after you push through 3-months, after Demo Day, after even a couple more months, you realize that while there will be improvements to your metrics, it still takes quite a bit of time to build a solid and foundational business. A business. Not a consumer sensation, not a build it and flip it for an acqui-hire (which is finally getting the amount of hate it deserves), but a business, that makes money, maybe even a profit.

So eventually, you’ll come to realize this and you’ll either decide 1) you can’t do this, so you’ll stop and get a job again (nothing wrong with that) or 2) you’ll sit down, get comfortable and figure out how you’re going to manage things thing for the long run.

Welcome to the awareness period. This is when you know you’re going to be heads down and you’re going to have to work your ass off for a long period of time to make this baby fly.

Fear = Your Biggest Enemy

As you navigate from bumbling to awareness and forge ahead, I’ve come to realize that your biggest enemy over the coming months/years is going to be your own mind, your fear, and your own ability to visualize success. Secondarily, as a founder, its going to be your own ability to extend positive beliefs onto the rest of the team to keep them moving forward as well.

Now obviously experiencing fear is all natural. And probably expected. Each of us got in this game because at one point or other we were in a situation of stagnation and decided we wanted more. But fear is probably the key thing that can lead to the greatest detriment during heads down mode — atleast in my mind.

I found that as soon as I could get my fear into check everything else became 10x easier.

A Calendar and a Graph

Now, to be honest, it took me a few months to come to a point where I had my fear in check. I did it by trying a whole lot of different things right along with working as hard as possible. But through my experimentation, I found these two key things to be the biggest help in staying aware, staying calm and carrying on:



  1. A 6-Month Calendar: In the main whiteboard at our office, we keep a whiteboard that maps out the next 6 months, with each month divided into 4 boxes. And in those boxes, we decided listed out as a team what our top 1-3 priorities for the week would be. These weren’t our tasks for the week, nor were they list of projects or anything. These were concerete things we wanted to work on and improve through the week. Not only did this help us “write the story” of what our next 6 months would be like, it gave us a good idea of whats important every week, where we’re headed and how things are going.We revisited this calendar every Monday morning and reviewed how the previous week went, whether we needed to reshift our priorities for this week or the coming weeks and how our overall plan was looking.

    Not only did this help us stay organized, it helped give me and the whole team piece of mind — it became our compass.

  2. A Graph of our Atomic Unit: the atomic unit for our service is an email. Fred Wilson recently blogged about the importance of knowing what the atomic unit for your business is. While there are a lot of other metrics that we look at, I always kept an eye on this guy because it told me over time whether we were fundamentally getting better in terms of usage (the thing that matters the most for any business).

In Conclusion

As I mentioned in my last entry, I don’t claim to have all the answers. In fact, I still continue to experiment and explore. But so far, this has been working quite well for myself and our team. The biggest thing I want to do is to get more founders talking about this heads down mode. To share more experiences, to have an outlet, and to talk more about what works and what doesn’t.


Categories: my thoughts.

Heads Down Mode

There has been two distinct stages to my life so far: 1) The stage where I started ToutApp and become a Startup Founder and 2) The stage where I dreamt of starting my own from scratch and lived vicariously through other startup founder blogs, TechCrunch and the 37Signals blog.

The one thing I always promised myself I wouldn’t do was go into the abyss once I actually started my company. I hated it when Founders made a ton of noise, shared a ton of insights, get a ton of PR, passionately talk about their startups but then went into complete silent mode shortly after they raised funding or hit a couple of milestones.

Needless to say, I did the exact thing that I found myself hating on others for. As ToutApp grew over the past few months, and as I switched cities, raised funds, defined the vision for the company and grew the team, I blogged less and less. I shared less and less insights. Even though I moved to Silicon Valley from New York because of the connected eco-system here, I’ve gone to exactly 2 networking events and one of them was by accident.

Why Founders Go Silent

So in true form of how this blog works, I decided to reflect upon why I went into silent mode. The easy answer is that I was too busy and no longer prioritized sharing my learnings with others. But I don’t think thats actually true. I still continued to talk to other founders and share my insights whenever someone reached out to me; infact, it is something I really enjoyed.

The slightly less of a copout answer is that I just didn’t want to be as transparent as I once was. As ToutApp grew to understand its market, its customers and develop our product, copycats started to arise. Whoever said that “imitation is a form of flattery” was bullshitting, its not flattering at all, its simply annoying especially when ideas you have worked hard to think deeply about and develop are copied into cheap knockoffs.

To say that competition and my need for less transparency was the reason I didn’t share as much about what I’ve been doing still feels like a copout. Dealing with competition deserves a separate blog entry of its own but I truly believe that the best way to beat your competition is to check in on them once a month but by and large ignore them and shift that energy toward stalking your customers — and so with that spirit, saying that I don’t share more of my thoughts because the competition will get a view into my thinking process is also not a real answer.

So finally, with those two relatively easy answers being struck out, I was left with one cold hard truth: I was afraid to continue to blogging because I didn’t have any amazing mind-blowing news to report.

No Amazing Mind-Blowing News = You’re On Heads Down Mode

The biggest thing I’ve realized in the journey is really how long it takes to make your business a success. We’ve been at it with ToutApp for nearly two years now and while there has been a ton of tremendous and amazing milestones with more to come including us fast approaching a 1,000 paid seats, when you’re two years in, unless you are a rare exception, you’re still somewhere in-between the “trough of sorrow” and “the promised land” — otherwise known as “Heads Down Mode.”

And while there is a ton of learning happening as you’re navigating this treacherous territory, it just feels akward sharing any of your learnings because you just don’t know if its validated learning or just a misconception thats going to take you deeper into the “crash of ineptitude.”

And so, following a line of many other startup founders who I’ve hated on before, I ended up doing the same thing. As I buckled down, I went heads down into focusing on our team, our product, and our customers and thereby slowed down on PR, slowed down on blogging and most importantly slowed down on sharing my learning.

We need to talk more about being Heads Down Mode

Just to be clear, although I’ve justified why I haven’t been blogging, I think the reasons are fundamentally wrong.

I’m going to make a conscious effort to blog more actively about being in Heads Down mode and I think other startup founders need to make a conscious effort about talking about this as well. Yes things are tough, yes in one minute you’re thinking “Holy Shit, we’re going to be a billion dollar company” and in the next minute you’re thinking “What the hell did I do to my life?” And yes, you don’t quite know if the conclusions you’ve drawn and the decisions you’ve made will take you out to the promise land, but still share those thoughts and learnings so that we can all get better as a whole.

We’ve heard this story time and time again. Start starts, huge fan fare. Start blows up and becomes an overnight success, and huge fanfare again. No one ever talks about the 3 years that happened in-between where the real “entrepreneuring” happened.

Let’s change that.



Categories: my thoughts.