Category Archives: Learning

10 things I have learned from running 10 demo days about #startup pitches

Ahh, the demo day. The arbitrary day the accelerator decides it is time to throw its babies to the world of investors. The number of accelerator directors I have asked the question “why is your program 3 or 4 months” is probably in the 50’s and the number of times I have not heard a thoughtful response is 100%. It is almost as if “that’s what everyone else does”.

This post though is not about being cynical, but more about what I have learned over the years and on what entrepreneurs can gain from my experiences of managing and running 12 demo days and helping close to 150 companies pitch, position and excite audiences.

First, it is important to set context. I am assuming you have a mix of investors and some non investors as well at your demo day. You have been through a 3-4 month program and have been practicing your “pitch” for a few months once or twice a month at least. I am also assuming that your pitch is about 3-5 minutes and your goal is to get investors interested enough to setup a follow on meeting to understand your company in more detail to express interest in investing.

I know that YC demo days have people in a frenzy with some investors texting they are “in” a round, even before the entrepreneur finishes their pitch, but for most parts I am going to assume that’s a rarity. For the rest of us, mere mortals, the pitch is an opportunity to prevent the audience from going to their smartphones distracted or otherwise bored by listening to pitch after pitch.

Here are the 10 things I have learned, in no particular order.

1. Show energy and passion – always be selling

You are in the spotlight, so if you dont wear your passion on your sleeve, you will likely get no attention. Even if you are a mellow person and tend not get excited much, find a way to show as much excitement you can about your company, the market and the opportunity. Investors are judging you and if “you dont seem excited about the opportunity”, they dont believe they should be either. You have been given an opportunity to sell your vision and this is one of the biggest opportunities you can get.
2. Visuals are only a prop – You should be able to tell your story without slides as well

Things have gone wrong with the deck or the projector only 2 times during the entire demo day for the 10 times we have done them, but those 2 times resulted in a meltdown for our founders. They were among the best in the cohort, but they forgot their pitch, got distracted and flustered when their slides went “blank”. Investors went believing that if they were to react this way if their pitch went dark, how would they react when sh*t hits the fan at their startup. Be cool. Use the Pitch deck as a prop alone.
3. Your goal is to a) get people’s interest to have a follow on discussion and b) to prevent them from getting distracted by their smart phones and c) ensure you are memorable enough for them to “tweet” about it, or make a note to email you for a follow up meeting

Dont imagine that someone will walk up after the pitch and give you a check. That would set you up for a high bar in terms of goal for your demo day pitch. You only goal should be to be memorable enough to get a follow on meeting.

4. Show traction – quickly after the problem and solution

Traction trumps all evils in a startup. Not a complete team, but have great traction – the investors think they can help you build the management team. Market sizing is still relatively small – the investors will try and help you expand to adjacent markets. But no traction? You cannot manufacture that.

5. Be specific about the total market, and addressable market

Most entrepreneurs have the time to only show the largest number possible and hope investors bite. Be more thoughtful than that. Over 60% of the folks that “went one level deeper” about addressable market, I have found, got a follow on meeting. The ones that showed a large gazillion dollar market, found investors ignored that number largely.

6. Tell stories that your day in the life has shown you, avoiding using phrases like – big problem, painful, etc.

If you generically use statements like “the problem is massive” for our customers, without being specific about the pain points, you are likely going to be dismissed. I’d highly recommend you use your “day in the life” scenarios to showcase what your user actually goes through as problems and how they are handling this right now.

7. Answer the question – why are you the best team to execute this problem

Many investors will tell you they invested only because they felt this was a great team and nothing else. That’s a lie. A big lie, but nonetheless, the team is one of the most critical aspects of any software opportunity. Just telling the audience who is in your team and letting them make the inferences as to why the team is uniquely suited to execute this problem is poor judgement on your part. Ensure that you let them know about your experiences, the fact that you have worked together, or that you have each unique learning that together helps build a great company.

8. Be clear about why and how you are different

In the absence of having something different to say, most customers (and investors) assume you dont have anything different, so you will compete on price. Competing on price is okay, but that usually signals a race to the bottom. The important thing I have learned about differentiation is that you have do something different in all aspects of your pitch – why is your team different, why is your product different, why is the market you are targeting different, why is your go-to-market different etc.

9. Your positioning forces people to figure out quickly if they are interested – get it right.

The first single line positioning is the thing almost everyone will listen to, which should be 5-15 seconds, when they are deciding if your pitch is worth listening to. Get it right and do it by A/B testing your startup’s positioning over time. Tweet-ready positioning is the best way to get some attention from the audience online.
10. Work your audience – Focus, 10 sec pause, Connect, Sweep 2 sec, Repeat. Make eye contact with as many people as possible. Engage your audience with a rhetorical question if you can.

These are tips for the folks that want to be a better public speaker. If your accelerator offers an opportunity to avail the services of a pitch coach, use it. As often as you can. While it wont make or break your company, the best public speakers generate more interest (not necessarily better, but more) for their companies than the ones who “show up and throw up”.

How to showcase the “problem you are trying to solve” in your overview deck #startups

This is a series of posts with a focus on your overview deck to investors, presenting your market opportunity, the team and traction your startup has had so far.

Customers, investors and partners want different levels of depth from your problem statement.

Investors want to understand the fundamental underlying trends of the market in the context of the problem you are trying to solve.

Customers want to understand the “day in the life” pain points that you help address.

Partners want to understand the contours of the problem in terms of the challenges that customers face.

You have to articulate the problem extremely well to get a buy in from all of the above audiences. Doing that solves more than 1/2 the challenges you have with getting buy in. The reason is because all of them believe that the person who articulates the problem best is the one who has likely the best solution.

Since you know the problem so well, you have thought about the solution as much is the assumption they make.

The best way to showcase the problem slide is to outline the trend that you are seeing in the industry first.

For e.g. Cloud computing is rapidly taking over enterprise deployments of new applications. Or, there is a dramatic rise in number of developers also performing the role of operations and this trend will continue until 2020. Or, there is a new role in companies which are progressively seeking to differentiate with great customer insight and the person in charge of it is called the Customer Experience Officer.

Now, it is important that you dont show that in the slide, but also provide your view of the impact that the trend has on your problem.

The reason this is important is that most every investor, and many early adopter customers will have access to these trends and will likely know about these trends already. For many of your late adopters, this might be news, but investors tend to be on top of trends for most parts, with some exceptions, especially if the are not deep in a specific category or industry.

So rather than say the generic statement, cloud is changing everything I’d offer a view on the way it is changing that affects the portion of the problem you are solving.

For e.g. Cloud deployments are increasing by 150% every year and that rise has caused a 220% increase in number of new Developer Operations roles, and these roles dont have the tools to be successful since the developer tools are available only to debug code issues, and the operations tools are focused on monitoring production instead of trouble shooting.

There are 3 tips I have learned to use when you share the overall trend part of your problem.

a) The trend needs to be something most people can relate to easily

b) the trend is best explained by using percentage numbers to showcase the growth (trend is your friend) and

c) the trend needs to have a disruptive nature to it, if you are playing in market with large incumbents.

The pain point part (2nd slide likely) is best explained when you have a day in the life of the person who is the user. What do they go through on a daily basis which causes them angst. What do they have to go though, which prevents them from being successful or causes them to waste time, or causes them to be inefficient in their job, or costs them more money than doing it with your proposed solution.

Any or all of these day in the life scenarios is usually explained best when you showcase what your user has to endure and how with your solution these go away. So in some ways, your user pain point should directly correlate to the solution you are trying offer that will solve these problems.

For example, the PR associate at a mid to small agency spends 3-5 hours going over google news and putting news articles into word, curating the influencers into an Excel spreadsheet and finally putting a report together that will share the key media coverage in a PowerPoint slide. This associate spends 3-4 hours every week doing this and we can do these things for them in less than 15 min.

There are 3 important tips I have see that work best to showcase your user pain:

1. The persona of your user and the “day in their life” has to focus on the top 3 pain points they have, daily. If your pain points are not the things that are high on their priority list, they will likely dismiss your solution as “nice to have”.

2. The best pain points expressed are in 3 specific things, not more. If you have one, then you will find your presentations to customers to be hit or miss, so you are better off, having 3 so the total surface area of the customer’s pain points are well covered.

3. The more “real” your pain point and the more they go through it daily, the better are your chances of getting customers to buy into the fact that you can empathize with them. The best way to test this is to ask questions of them to seek engagement. For e.g. “Raise your hand if you find yourself struggling to quickly understand which emails are important and which ones are not, after a quick 15 second glance on your email client”.

Let me know if these tips work.

How to be a more innovative startup by changing just 2 words in your meetings daily

Most every startup wants to be innovative. That’s the essence of being in a startup. To be innovative, most entrepreneurs realize they have to get their culture right. An innovative culture fosters and innovative workplace which builds an innovative company.

So, now the question is how do you build an innovative culture?

To build an innovative culture, I believe you have to encourage experimentation. Lots of it. Most people learn only by experimenting, not by sitting in classrooms and being taught. While it is important to sit and learn the first principles, most everything else needs to be learned by doing. You will have to let people try lots of things and learn what works for your company, your industry, your market and your customers.

The trouble with experimentation is that it breeds failure. Lots of failure. If everyone of your experiments were successful, then you are not taking enough risk, which means the company wont be as innovative. In fact, the leading indicator for innovation in most companies is the number of failures they have. Which means they are taking more, but managed risk. A good metric to measure, is the # of experiments your startup conducts in a unit of time and what the failure rate is.

The best way to do this is to practice the art of disciplined experimentation. Which is why I am a fan of the phrase “My discipline will beat your intellect“.

So, if you do conduct a lot of experiments, you will fail. How do you understand, organize and learn from your failure?

Most companies conduct an audit of their experiments, the hypothesis, the initial learning and the final results. That’s where the the biggest problem is to be found.

Most managers and executives are trained to ask the question –

“Who to blame”?

That’s the question that most meetings post experiments start with? What happened? Why did it happen? Who is to blame?

I propose a small change instead, which will get your people less defensive, more open to taking risks and experimenting.

The right question to ask is –

“What to blame”?

Focusing on the process, steps, methodology and systems brings out the best answers to the question “how do we get better”?

Surprisingly you learn more about people, their strengths, limitations, weaknesses and biases if you focus on the process that was broken instead of assuming that the people messed it up.

For most founding entrepreneur CEO’s this is one approach that works best to foster a culture of innovation and risk taking.

Do you have a manager who has followed this principle? I’d love to understand what you have learned from them. Drop me a note on Twitter. (I do respond to all @ replies BTW).

How to A/B test your startup’s positioning statement

I had a chance to talk to 2 of our startups at the accelerator yesterday and we discussed positioning. One of the first things that we focus on is to ensure you position your company and product well. That may seem like “fluff” and “soft” to many folks, but we find that to be critical to ensure that people who you interact with – customers, partners, potential recruits, investors, etc., get it quickly and accurately.

What I have found is that depending on the background of the entrepreneur, the positioning statements tend to be very long, mostly filled with buzzwords – (no, really 99% of the people in this world dont know ARM, resin-conductors or DevOps, and most likely 90% of your target audience does not either) or overly complicated.

The positioning statement should at its simplest help explain who you are at your core.

Most folks will try to explain their positioning by using the framework below.

For (specific customer description):

Who (has the following problem):

Our product (describe the solution):

That provides (the following difference):

Unlike (your competition):

Now, for most parts this was 15 years ago. This is still a valid exercise for you to come up with your positioning, but most of this may be not as effective in our Twitter driven world.

There are 3 more manifestations I have seen for this statement:

1. Position your company / product in less than 8 worlds so that someone coming to your website can get it in less than 5 seconds

2. Positioning by successful similarity – We are XYX (an awesome product, e.g. Uber) for ABC (a very large market, e.g. school kids needing rides)

3. Retweet ready positioning – A positioning statement that is retweet worthy, so it should be less than 100 characters – so you can still provide a link to your website

The important thing to note is that your website should reflect positioning for your biggest audience – target users or customers, not potential investors or employees.

I am also not a fan of using multiple positioning statements by audience – so you should avoid telling investors you are a disruptive solution for ABC market, and tell potential employees you are X for Y.

It never adds up and wont scale.

Instead, I’d recommend you start with first making a list of segments of your customers. Preferably you are able to segment a small niche customer segment to start.

Then write down the list of problems your customers have. For example. a) the existing products are too hard to use b) the existing solution is too expensive c) the existing solution is to do something manual d) potential customers are unable to be successful since no solution exists to help them with this pain, etc.

Then you have to document the features of your product that correspond to solving the problems you listed above in the problem statement. For example: a) Our export to excel feature allows customers to get the data via API’s b) our API based mechanism lowers cost of delivery. etc. This is also sometimes the “how you do it”.

Then you have to record the differentiation associated with the features. How do you do something different to enable that feature(s). For example: our algorithm for ranking generates a proprietary score for each customer segment.

The next step (which you may not need for the positioning, but will later on) is to document the benefits of the feature / differentiation. Benefits are fairly easy to document based on cost savings, revenue generation, etc. and are based on the feature list. For example, if you have X feature and Y differentiation, that results in a reduced cost compared to existing competitive solutions for customers,.

This should suffice for you to start A/B testing. Now, use these in your web copy, presentations and when you are describing your company to others at events, meetups, etc.

Keep a log of the first 100 people (or some good enough sample size) of people you to talk to, and get a sense for which statements resonate.

Test different positioning statements until you get to the minimal set that gets people exited enough to ask you to tell them more.

Until that point, keep testing.

Before you know it, your startup is now a “big” bureaucracy with “approvals” for everything

Often when I meet wannabe entrepreneurs at events, I ask the question, why they are willing to give up their relatively easy job, with good pay to take up the roller coaster world of starting their own company. About 20% or so of the folks I meet at these events work at another startup (typically < 3 years old, about 20-50 people). I think of most of these companies as startups as well, so I am curious as to why, after seeing all that happens in an early stage startup, they want to start their own company.

Sometimes it is because they want to be their own boss, or they see the success of the founders, who they claim have little intelligence, but still managed to start their own company and be moderately successful. At other times, I hear the burning itch to start and solve a problem or other times it is because they always wanted to start one, but were not able to because of other constraints.

Every so often I will get a person who was the 1st or among the first 10 employees of a startup. They will reminisce about the “early” days of the startup they are working at and talk about how everything was simple and easy during those days and how bureaucratic their 50-100+ person startup had become.

When I press further about the “bureaucracy” and what makes things slow and inefficient, the word that always comes up is “approvals”.

“Approvals” are the tool misguided managers use to make themselves feel important.

If you are a person that needs to feel important so you can “approve” things, you dont have enough work to do.

Approvals are used by big companies to kill any ounce of individual responsibility and trust. They also kill the very initial set of values and culture that you might set out to build your company’s foundations on.

Approvals send one of many messages:

1. I did not hire the right person so I have to ensure they “stick” to the rules of the company that HR has arbitrarily come up with.

2. We have hired way too many people who dont have enough work to do, so they have to be around to “approve” things.

3. We need policies and procedures for everything since we dont trust the folks we hired to use their judgement.

Notice that the common word in these (and most other) examples is “hiring”.

Approvals are the child of poor hiring and recruitment.

You can cop out and say it is a HR problem. It is not actually.

As a founder, it is your responsibility to ensure that the vision and culture of the company are consistent with the ethos you started it out with.

The first 10 employees are indicative of the zeal you brought to the table, which convinced them to join a high risk startup at such an early stage.

If these first 10 and many other employees feel that the company is “approval” heavy and requires big company (productivity killing and sans accountability) procedures, then you have something wrong with your hiring, not with your HR policies.

Remember this, if a manager in your company feels so important to want to “approve” everything anyone does in his organization, he has practically no work and likely a heightened sense of importance.

Reducing complexity and making choices – things I learned from Apple’s product designs

The other day a friend who was closely watching the Watch and Macbook announcements mentioned to me that Apple had introduced its new notebook with only one port – the USB C.

He gave many examples of why he need more ports, simultaneously, including charging the Macbook and a phone at the same time, for example or being at your desk and transferring files from a USB flash drive.

I thought they were all good examples actually, and situations I had faced before. Then I decided to challenge all the assumptions he had made with the fact that those situations are the exception not the norm.

With a battery life of 12 hours, there were very few situations where you will need to charge and give your iPhone some juice as well. You could plug the notebook from the power unit and it would go for hours even if it had to charge your phone. Similarly with its long battery life, the chances were slim that it would really run out of charge for “normal” usage.

Then it struck me that most of us do the same thing with all of our daily possessions. Take a look at your backpack for example. There are surely 100’s of things that I have in my own backpack that I have rarely used, but need for a “rainy day”.Truth is, during those “rainy days”, I had options.

I dont need 3 pens because there are 3 pen slots in my bag, neither do I need my check book, etc. I dont need a backup credit card – well I have not for the last 3 years, but I do carry them all and more things.

I believe we make these choices because of our fear of “what if” and apply it to the worst case situation. Which to a large extent prevents us from the “what if” and enjoy the best case scenario.

Optimize for the “likely case” and plan for your options might be a better situation – at least in my case. I think that’s a key learning from the USB-C port discussion.

Trying to save for a rainy day is great, but too much saving results in most days being gray, without enjoying the sunshine that’s all around us.

Trends among the Ultra High Net Worth Individuals that will shape Global attitudes

There are 170K+ individuals in the world who have more than $30 Million in net worth according to the Knight Frank report on UHNWI. They own a total of over $20 Trillion in wealth. That’s a staggering 25% of all wealth in the world. Owned by less than 0.00001% of the population. By 2025, the number of UHNWI is expected to be at 230K.

Over 82% of these people had their wealth increase over the last year (2014) and over 80% expect it to increase the next year as well.

The biggest concern about their ability to generate more wealth (as if that’s needed) was family succession issues.

What does their asset allocation look like? 45% in equities (stocks), 10% in home (property) and rest in other assets (cash, gold, art, etc.)

Where are these UHNWI located? 45K in the US, 60K in Europe, Latin America has about 10K and Asia the rest at about 40K+.

Surprisingly only 40% were inherited wealth. The rest made money via entrepreneurial means – real estate and “other business” were the top professions. Technology UHNWI were less than 5% of the total.

The other surprising part of the equation is that there are 1844 billionaires, 38K $100+ Millionaires and over $172K UHNWI. Over 17 Million people are merely millionaires. Turns out the millionaires are the new lower middle class.

As the “poor” become “richer” the “rich” get “wealthy”. There is a direct correlation between the increasing middle-class, their aspirations and the wealth of the UHNWI.

The most important cities where you should look for UHNWI – London, New York, Hong Kong and Singapore top the list, San Francisco is in the top 20, and Mumbai is the only Indian city in the top 50.

The air traffic information from private jets is another interesting story within the story. The top 10 routes for private jets are mostly from and to the US, but the fastest growing are mostly to the US from other places. Meaning even if wealth is created elsewhere, most end up in the Americas – to invest, to hang out, etc.

Where are they going to and where are they coming from? They are going from China, India to the UK and Singapore.

So where’ the money – Chinese investing in Miami, commercial properties in New York and London.

The Indians are investing in Europe more – London, Zurich (not a surprise here).

If you are an entrepreneur looking to raise funding from UHNWI, you should expect to meet with their adviser than with them directly apparently. Most of the UHNWI prefer to work on their own business and spend less time mentoring or guiding anyone but their own kids.

Overall it is a very interesting report. Worth a long plane ride read.