Connect with us


What Startup Entrepreneurs Can Learn from Donald Trump



Learn from Donald Trump

I am not a fan of Donald Trump and dont agree with many of his positions, but he sure is entertaining to follow. I do actively follow politics, so I am keenly interested in campaign strategies, tactics and political news.

There’s a lot to learn from Donald Trump, in terms of startup strategy. There’s a great piece about him on Business Week, which is a good read.

Here’s the TLDR version – he inherited a lot of money from his dad, started building and did some real estate development, lost a lot of money, bankrupted his companies and then started fresh again.

Instead of risking a lot with loans, he instead, created a “branding and merchandising” entity which lends the Trump name to real estate companies. This licensing is how he makes a lot of money – risk free.

The 3 most important lessons I learned from him so far are:

1. Disrupt the incumbents and “insiders” by creating a new set of rules to play by. Political campaigns, we are told are about issues, depth of knowledge and having strong positions on those issues.

You need to be broad and deep on the issues – know who the president of Syria is, as well as the unemployment rate in rural Iowa and the daily working class problems of a single mom in Florida. Which realistically most candidates don’t have.

Trump, but no means is an expert (for most of the things that you need to be an expert on to be a President). In fact, he is the antitheses of an expert. He has forced all the other “institutional candidates” with pedigree and great backgrounds to make illegal immigration the #1 issue for the election.

Which, in itself is surprising, given how little impact it has on the economy or social well being. It does though, have a huge cultural impact.

The incumbents, now have to play by his rules and are falling all over themselves, looking like fools, and giving answers that indicate that the solution to every problem is to build a wall.

2. Make your competitors biggest strength their biggest weakness. Most political campaigns are about fundraising. You have to bring enough via small donations, contributions from rich investors and retail money (think $1000 private dinners).

Most of the competitors have been trying to do that, just like the establishment of the Republican party – which is confused as to how they can “checkmate” Trump. Well, their biggest strength (fund raising) is now inconsequential. Trump has spent no money (not really, but much less than his competitors) but has been constantly getting the attention and the coverage to be “in the news” all the time.

The rich Republican donors who want to stop him on his tracks are a loss to figure out how to do so, given that their money (with which I presume they can buy attack ads) is not going to buy them much at all.

3. Being an outsider in an industry helps frame everyone in that industry as “old school” and “dithering” to potential customers. Most customers like new approaches from other industries, even though they understand that 100% of them may not work .

Trump’s solutions for building walls, making Iran “pay if they violate the contract”, etc. are unlikely to work in the political arena, which are purely business ideas, but he has framed them well enough for people to think there’s a shot it might work.

I actually am among the few people who think Trump will will the nomination of the Republican party, since the rest of the crowd (save Marco Rubio) are just not that exciting. If, he does that, then he has a great shot at being President.

Imagine that. That’s the startup equivalent of an Unicorn. Very little chance of happening when you started, but going against an existing set of players in a predefined market, making it easy pickings at times.

Continue Reading
Click to comment

Leave a Reply

Your email address will not be published. Required fields are marked *


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.

Continue Reading


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.

Continue Reading


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.

Continue Reading