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10 Things I Have Learned from Running 10 Demo Days about #Startup Pitches



Demo Day

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”.

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Creating Artificial Constraints as a Means to Innovation




Artificial Constraints

Many of the entrepreneurs I know have created new innovative startups thanks to real constraints they had. For example, I was hearing AirBnB’s Brian Chesky, on the Corner Office podcast and he mentioned that when he and his cofounder were trying to get some money to get started and the only way to keep afloat was to “rent” their air bed they had in their room. That, then led to Air Bed and Breakfast, which is now AirBnB.

This was a real constraint they had – no money to “eat” so they had to make it happen somehow.

I have heard of many stories of innovation where in the protagonists had real constraints of either financial, technology, supply, demand, economic, social or any number of other characteristics.

The interesting story that I have also recently heard of how Facebook has “pivoted” from being a desktop offering to getting a significant part of their revenue from mobile is how they were given the arbitrary constraint of only accessing Facebook via the mobile phone.

So there are ways that you can create “artificial” constraints to force innovation to happen.

Most larger companies and some smaller ones as well, have to constantly find ways to create artificial constraints – to find a way to innovate and be more be a pioneer.

While some constraints are good – lack of funds at the early stage for example and lack of resources, there are entrepreneurs that are stymied by these constraints and those that will find  a way to seek a path to go forward.

I think this is a great way for you to think about innovating in a new space. If you have constraints, find a way to use it to your advantage.

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The Great Mobile App Migration of March 2020




Mobile App Migration

Over the last few weeks as many in the world have been in lockdown, there has been a temporary “mobile app migration” happening. There are new apps downloaded and they replaced existing apps on the “home screen”.

While some of these apps are likely temporary use, for e.g. I have 6 “conferencing apps” – Zoom, Uber Conference, Webex, Google Hangouts, Blue Jeans and Goto Meeting. That is because of the many people I have conference calls with – each company seems to have chosen a different web conference solution.

Other apps seem like they will have staying power – Houseparty, for e.g. which has games, networking and video conferencing all built into one app to keep in touch with friends and relatives.


The apps that have moved away from my “home” screen, which I expect will come back once the crisis will be behind us include – Uber, Lyft and all the airline apps from Delta, Alaska and United.

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Perseverance with the Ability to Pivot on Data: 21 Traits We Look for in Entrepreneurs




Perseverance with the Ability to Pivot

There are 5 key inflection points I have noticed which makes founders question their startup, to either make a call to continue working on their startup, pivot to a new problem or quit their startup altogether.

It is at these points that you really get to know the startup founder and their hunger and drive to be successful. I don’t think I can characterize those that choose to quit as “losers” or “quitters” because of many extraneous circumstances, but there is a lot of value that most investors see in entrepreneurs who face an uphill part of their journey to come out on the other side more confident and stronger.

These five inflection points are:

  1. When you have to get the first customers to use and pay for the product you have built after you have “shipped” an alpha / beta / first version. Entrepreneurs quit because they have not found the product-market-fit – because the customer don’t care about the product, there is no market need, or the product is really poorly built, or a host of other reasons.
  2. When you have to start to raise the first external round of financing from people you are not familiar with at all. Entrepreneurs quit because while it is hard to get customers and hire people, it is much more harder to get a smaller set of investors to part with their money, if you do not have “traction”, or “the right management team” or a “killer product”.
  3. When you have to push to break even (financially) and sustain the company to path of being self sufficient. Entrepreneurs quit at this stage because they have now the ability to do multiple things at the same time – grow revenues and manage costs, and many of them like to do one but realize it is hard to do that without affecting the other. So, rather than feel stuck they decide to quit.
  4. When you have to scale and grow faster that the competition – which might mean to hire faster, to get more customers, to drive more sales, or to completely rethink their problem statement and devise new ways to grow faster. Entrepreneurs quit at this point because they are consumed by the magnitude of the problem. They overassess the impact the competition will have on their company, give them too much credit or focus way too much on the competitors, thereby driving their company to the ground.
  5. At any point in the journey, when the founders lose the passion, vision or the drive to succeed. Entrepreneurs quit a these points because they have challenges with their co founder, they don’t agree with the direction they have to take, or encounter the “grass is greener on the other side” syndrome.

While I have observed many entrepreneurs at these stages at  discrete points in time, I have also had the opportunity to observe some entrepreneurs in the continuum, and I am going to give you my observations on 3 of the many folks I have known, who, have quit.

Perseverance separates great entrepreneurs from good ones
Perseverance separates great entrepreneurs from good ones

One went back to college to finish his MBA after getting a running business to a point of near breakeven, another found the business much harder than he originally thought he would and got a job at a larger company and the third was just unable to have the drive to go past 11 “no’s”‘ from angel investors.

Over the last 8 years, if I look at my deeper interactions with over 90 entrepreneurs, who I would have spent at least 100+ hours each, I would say that of the 24 people that are not longer in their startup, the one thing that stands out among the ones that persevere is that it is not “passion” or “vision” at all.

It is the inherent belief that they are solving a problem that they believe is their “calling”. They also don’t believe that there is any other problem that’s worth solving as much, even though there may be easier ways to make money.

So most of my questions of entrepreneurs to test whether they will pivot or quit are around why they want to solve this problem (which I am looking to see if they know enough about in the first place) versus any other one.

The answer to that question is the best indicator I have found to be the difference between the pivots, the leavers and the rest.

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