5 Questions Founders Need to Ask, Annually

“Can I meet with you today?”  Usually, when I get such a call, which I do about once in two weeks, the entrepreneur wants to meet immediately. In this instance, I suggested that we can meet the next Tuesday. The entrepreneur, let’s call him Jack, persisted, “If it’s okay can we meet today please?” So I agreed we’d meet at 530pm that evening and moved around a few meetings to make it happen.

At about 445pm I get a call. It’s Peter, Jack’s partner. He says “I’m going to be about 10 minutes late.” As I’m wrapping up a meeting, I tell him “Don’t worry about it. I will be at the coffee shop. See you there.” At that time, I didn’t pay attention whether Peter had said “we’d be late” or “I’d be late.”  So at 530pm, I’m surprised to see only Peter show up with no sign of Jack.

“So what was so urgent that it couldn’t wait till next Tuesday?”

Peter was polite enough to apologize for Jack’s absence, “A major customer crisis has arisen. Jack had to go in person to placate the customer,” before jumping into why he’d asked for the meeting.

“BigCo has made us an offer. We’d approached them as a strategic investor. As we talked to one another, the discussions turned into an M&A one. They are interested in acquiring us. So we’re looking for advice on what we should do.”

Over the previous six years Jack, Peter, and another partner had at first bootstrapped their tech business and then raised both an angel round and a series A. They were on the verge of operational breakeven and had impressive Fortune 100 customers that any startup would kill for. They’d also dabbled in hardware and systems, pivoted a couple of times and overcome significant challenges in pulling together a fragmented supplier marketplace. In short, they were not just smart and hardworking but successful by any measure.

“What do you want?” I asked. “What does Jack want?”

Peter’s responses, many of which were questions rather than answers, sounded similar to ones that I’d faced more than a decade ago when my own startup was acquired. And one that I’ve heard from many entrepreneurs since. Most founders rarely stop during the madness that is doing a startup is, to ask, let alone answer these questions. So regardless of where you are in your own startup journey, here are some questions for you to ask yourself. I’d suggest revisiting these once a year, more frequently they’d be a distraction.

What do you want? Why are you running/doing a startup? To make a zillion dollars? Because people don’t have easy access to mental health? Because every kid should go to college? Whatever be your reason – only money, only greater good, some combination of both or yet another reason, knowing what it is, is important. This will help you figure out, are you close to it? And regardless of your distance from it, do you want to keep doing it?

How much money do you want? Despite startups being businesses, many entrepreneurs haven’t really put thought into how much money, specifically, they’d like to make or have. So when they are faced with a sudden offer to sell or particularly when they face a hostile or shall we say unwilling ejection, they are in no position to figure out what they want in any dispassionate manner. Surprisingly many entrepreneurs, starting with myself, find that they are uncomfortable talking about money for themselves. So this is a good question to answer if only to get comfortable talking about it.

What do your partners want? Usually your co-founders, especially at an early stage startup, much like you would also have not given this much thought. But in some cases may have greater clarity, which is usually a good thing, but you’d better know what it is and how different it is from your own answers to the question. Again, they may have thought of things only in terms of money or in terms of outcomes and not money. Knowing the answer to both and knowing your differences will be immensely useful.

What does your team want and what do you want for them? This may or may not matter to you, or you may even be unclear if this matters to you or not. Knowing this is critical at some many practical and even ethical reasons. For instance, what matters to them – that they work in a startup, the freedom or independence they get maybe very different than what they get from BigCo once they acquire you. What are they likely to get monetarily if you sell your company?

What will you do tomorrow, if you get what you want? If your company were to be acquired today, in an all cash deal, with no strings attached (and let me know if there are such deals out there 🙂 what will you do tomorrow or ninety days hence, after you take that well-deserved vacation. In many ways, this is similar to the first question around purpose? If you’d still do what you are doing today, what does that tell you? And if you’d do something totally different, what are you waiting for – what should you do differently today?

I believe if you ask and answer these questions both individually and collectively as a founding team, periodically, it would help you make better decisions when you are at crossroads in your startup.


As many companies that I’ve been involved with grow past their fifth or even seventh anniversary, they are facing new questions around exits – be the outright sales or mergers or in some case existential questions. I’m hoping to write about these questions in what I’d like to think of as “Selling your startup” series.

Entrepreneurs & Mental Health

This last week, Brad Feld, a managing director at Foundry Group in Boulder, Colorado – shared a video (below) he’s made for an upcoming event about Entrepreneurship & Mental Health. Brad as an entrepreneur who went on to become a VC belongs to the small group of VCs (including Fred Wilson, Mark Suster) who are both prolific and compelling writers – demystifying the venture world, entrepreneurship and often taking a very pro-entrepreneur stand. I’d thought of Brad alway as different given his location in the Rockies (Colorado) rather than either of the coasts (Silicon Valley, Boston or New York) where most of the well-known VCs are based.

Brad’s open discussion of mental health issues, including his own depression, that he’s written about (here) and spoken about (here) makes him a very special person. In India, we’ve seen folks such as Indian actress Deepika Padukone recently talk about her battle with depression (video) and young entrepreneurs such as Richa Singh, who founded YourDost, and Shipra Dawar who started ePsyClinic try to help young people address mental health issues. Last October at the demo day of the Brandery, I saw Jordan Axani present his startup Bounde, which is “Tackling mental health through technology.”

In India, as many folks have commented two big challenges lie in the way of people getting the mental health support they need

  • Social stigma – both ignorance and the stigma (or fear of being branded) mentally unstable
  • Access to good counselors/psychologists and psychiatrists

In the US while neither of these issues is fortunately as big a hurdle, as Brad points out in his video – entrepreneurs in the US (and in India) suffer from the social pressure (real or perceived) of having to be strong leaders, without too much any self-doubt or exhibiting weakness. Also in both countries, certainly in the entrepreneurial ecosystem, there is little or no talk of mental health issues – which is a big shame. With folks such as Brad talking about it openly and with young entrepreneurs who’ve faced mental health issues themselves or seen in around them, we’ve taken the first step.

Entrepreneurship is hard enough without physical, emotional or mental health issues. But addressing these is critical for both individual entrepreneurs and the ecosystem. And talking about it is the first step. So break the silence and talk about it. Doing so gives others both permission and encouragement to do so. What are you waiting for?

Negotiating well in groups

The entire company, probably little over 50 people, was in the room. It was the 9th of December 2005 and we’d gathered to discuss the news that we were seriously considering an offer to sell the company. Nearly twenty people in the room had been with us more than five years – through two major pay cuts and one minor layoff – another 20 with us over the last two years, when it was certain we were no longer going to die. So the topic of the meeting and its consequences were not merely financial or professional but deeply emotional. If we chose to be acquired, our success largely lay in the hands of the folks in that room, in their willing participation and agreement to the decision to sell. Early in the meeting, we posed the question what would be your biggest fear or concern, should we sell the company.

As you can easily imagine when you pose such a question, to a large group of people, none of whom were at a startup because they were shy or retiring, things could easily degenerate into a free-for-all. Also while we had planned to take half a day for the meeting, there was a lot of ground to cover. So the challenge we were posed with was, how do we get the team to not only have their say, but to get them to converge on a few important things, such that the biggest concerns not only get aired, but acknowledged and ideally even addressed in the meeting.

Amazingly the 50+ people were able to converge on their three primary concerns and were unanimous with their first concern – “What would happen to our culture, if we are acquired?” thanks to a technique called Nominal Group Technique. And were able to do it within 15 minutes. This is a technique that I’ve had the opportunity to use repeatedly in groups, as small as 8 people to as big as 55, – to get rapid convergence – often from a standing start – of even what the key problems were that we needed to solve and what are the top 3 or 5 things to do to solve them. The technique requires that I write a whole another blog post dedicated to it to explain the manner in which we’ve used it, adapting it for different groups not just across countries but across age groups, and different socio-economic backgrounds. This morning I read about the a technique called Indaba, that was used at the recent climate conference (COP21) to get nearly 200 nations to sign-off to a binding agreement.

Negotiations are difficult by nature. Managing negotiations between 195 countries in order to arrive at a legally binding agreement, on the other hand, is nearly impossible. This was the problem that United Nations officials faced over two weeks at this month’s climate-change summit in Paris. To solve it, they brought in a unique management strategy.

The trick to getting through an over-complicated negotiation comes from the Zulu and Xhosa people of southern Africa. It’s called an “indaba” (pronounced IN-DAR-BAH), and is used to simplify discussions between many parties. Read the full article here.

If you reckoned negotiating with one party was hard, be it with an employee wanting to leave or customer or partner wanting more for less, negotiating with more than one party is incredibly more complicated. Luckily there are proven techniques that can help you do so successfully. It would be good to get acquainted with them, well before you’ll actually need to use them. Better yet, try ’em out today!

I’ve written about negotiating before here and conflict resolution here.

The gender wage gap is not misleading

For example, it’s true that not as many women choose to become mathematicians versus, say, high school math teachers. But is this really an independently made choice that young women take? Or is it socialized choice?

As the father of two girls, I’m always interested in what we as society and the communities we are part of signal to our children – especially when they are growing up. As the Cathy O’Neill, aka mathbabe looks at the gender wage gap (in the US) it presents a glass half full picture. Read the full article here  The gender wage gap is not misleading

How Shipping Container Changed the World

Often Om Malik shares interesting reads – this was one he shared y’day. I found it interesting for two reasons – good stories can be about things (in this instance containers) and not just people and many more engineering stories, like this, that impact nearly everyone of us needs to told more often. I’d love it if you share other stories you’ve read.

It took a pugnacious North Carolinian named Malcom McLean to launch the container revolution. An ambitious truck-company owner with little experience when it came to shipping, McLean—who had made a fortune in trucking in the boom years after WWII—was looking for a way to move goods up and down the East Coast’s traffic-choked highways faster and more cheaply.

via How Shipping Container Changed the World.

Brandery Demo Day Insights

The Seed Accelerator Rankings Project reports over 150 accelerator programs in the United States. In India too we’ve seen a large number of accelerators pop up over the last two years. Yet this last week, Dave McClure of 500Hats was quoted saying “If you think that running a startup is a bad idea, then running an accelerator is an even worse idea” at StartupIstanbul.

Tweet from StartupInstanbul

Yesterday I attended the Demo Day at Brandery, (ranked #12 accelerator program) based out of Cincinnati, thanks to an invite by Tony Alexander, ex-entrepreneur and GM of the Brandery.  The day was eventful for many reasons – all of which I’m hoping to write about. But the thing that struck me most was how the Brandery has followed much of the advice we give entrepreneurs to set itself on the path to success. Not just accelerators but regional ecosystems everywhere can take a leaf or two out of the Brandery’s playbook.

By playing to their strengths and clearly articulating what those are, the Brandery have set themselves up for success. The short version:

  • Focus strong & narrow focus on branding, marketing and design, playing to their strengths
  • Partnerships Strong local ties with consumer goods & retail firms – both as investors and partners
  • Geographic Mix Attracting startups from around the country (& the coasts) to magnify networks
  • Metrics Measuring and reporting key outcomes – exits, startup equity raised, jobs created
  • Long game focusing on their entire ecosystem and the long run gets community commitment

Of course they offer the table stakes that all accelerators & incubators need to bring – strong mentors, equity, good cohorts and co-working space. I’ll get a longer version of the insights garnered hopefully soon.

How to Talk to Journalists

Despite having been through four startups – and dealt with journalist across two continents, it never is too late to remind oneself of what it is that journalists are looking for and how best to build relationships with them. Great piece by Pete Warden

Pete Warden's blog

newspapers

Photo by Jon S

Now I’m at Google I don’t get to talk to reporters, which is a shame because they’re a lot of fun. When I was doing startups I learned a lot from hanging out with them, because they’re generally very smart, curious people who have a lot wider perspective on what’s happening than anyone else. I even dabbled in writing articles myself at the old ReadWriteWeb site many years ago.

I was talking to a startup founder recently, and realized she didn’t actually understand the basics of what a journalist’s job is like. Knowing the day-to-day routines and constraints on reporters is essential if you’re going to do a good job helping them cover what you’re doing.  Here’s my advice, based on my personal experiences over the last few years. I’d love to hear more from other people too, since I think this is far from the final…

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Anger & Knowing One Self

ConflictLike nearly every family WhatsApp group, mine if often filled with all kinds of forwards – that I tend to largely ignore or quickly glance and not dwell too long on. This morning my sister shared this piece on WhatsApp and it made me stop & think. It’s always sobering to see oneself in the mirror.

As entrepreneurs, there are a million things that frustrate us, tick us off and many times we want to scream at someone – some of us do, others keep it inside and the rest try to drink it off I assume. But this little story or parable brings home the message of “responding and not reacting” – to recognize our reactions stem from what’s inside us and not things that happen outside of us. Enjoy.

A monk decides to meditate alone, away from his monastery. He takes his boat out to the middle of the lake, moors it there, closes his eyes and begins his meditation. After a few hours of undisturbed silence, he suddenly feels the bump of another boat colliding with his own. With his eyes still closed, he senses his anger rising, and by the time he opens his eyes, he is ready to scream at the boatman who dared disturb his meditation. But when he opens his eyes, he sees it’s an empty boat that had probably got untethered and floated to the middle of the lake. At that moment, the monk achieves self-realization, and understands that the anger is within him; it merely needs the bump of an external object to provoke it out of him. From then on, when he comes across someone who irritates him or provokes him to anger, he reminds himself, “The other person is merely an empty boat. The anger is within me.

Is Success Even the Right Metric?

“How can I be as successful as ….?” This is a question, that not just my daughters ask, but many of the young people I meet. Of course, this gives rise to the question “What is success?” No two people define success the same way.

While I’ve read and heard a variety of definitions, I feel, VR Ferose, the former Managing Director of SAP India said it best. Success is personal and often about yourself. To the young man who is the first in his family to have attended or graduated from college, that is a success. To the security guard at his company who’s the first, from his village, to have landed a city job that’s success. To the young woman who became the CEO of a tech firm, success is attaining that post.

So doctors, engineers, lawyers, politicians all believe various things that they have achieved or seek to achieve as their success. But is success even the right metric for our lives?

I’d argue, as Feroze did that day, that impact, what impact are we having or will have on others lives is a far better metric. Unlike success, where the focus is on you and your accomplishments, impact is about other people. “She’s created over 200 jobs, as an entrepreneur” or “He’s helped 30 kids graduate from college.”

Does this mean we should quit our jobs or not pursue “selfish” goals such as running a startup? No, absolutely not. But we should revisit how we measure what we do, what we believe as success in ourselves and others. Entrepreneurs are among the greatest contributors to society, whether simply as inspiration to others or in creating real impact on the ground it terms of wealth or job creation,

Does a Babajob, create new economic opportunities for those in the disorganized service sectors? Hell yeah! Does Vaatsalya enhance the quality of health care and life for folks in Tier 2 & 3 towns? Certainly. I’m sure you can think of many more. Of course, their being financially viable as a business is important to deliver the impact that they do. However, measuring or celebrating entrepreneurs and their companies as a success merely because they raised a round or their founders are cool is both limiting and unimaginative.

So what is the impact you and your organization are going to have today?

8 Secrets of Success

As the father of two teens, there are many moments when my children ask, even implore, me to “Just tell me what to do!

As a parent, it’s hard not to TELL your kids what to do. Of course there are far more times when they don’t want to hear the things I’d like to share with them. Mentoring entrepreneurs in many ways not that different from raising teens – you’ve gotta resist the urge to tell them “the answer” even when they ask for it and you’d better get used to your advice not being adhered to or at times even heard.

That of course never stopped me as an entrepreneur, mentor or parent from sharing, lessons and insights that I never cease to learn. Even while urging kids or entrepreneurs to focus on impact and the journey, rather than “success” – the question of how does one get to be successful comes up all the time. Luckily better men than me have grappled with this issue and here’s a short (3.5 minute) video that answers this very question. For those that prefer to read over watching a video, however short, I have provided a short summary at the end.

The eight secrets are

  • Passion – be passionate about what you do (& the money will follow as Marsha Sinetar put it)
  • Work – work hard but have fun. As Richard St. John puts it, be a workafrolic and not a workaholic!
  • Focus – focus – on one thing is critical to being successful
  • Persist – persistence is an attribute that comes up consistently
  • Ideas – be creative and constantly come up with new ways to think & do
  • Good – practice, practice, practice – so that you get good at what you do
  • Push – you have to push yourself, past doubts & doubters, obstacles to be successful
  • Serve – be of service, whether with your business or product or in life