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Top 5 Tips on Coming Up with #Startup Metrics That Align with Milestones



Startup Metrics

Startup milestones both internal and external help you understand and explain how your company works, grows and scales. While most entrepreneurs will continue to tweak their milestones and keep setting new ones as they scale, the metrics that underlie tend to change as well.

The way to think about metrics is that it should answer the question:

If we align all the resources at our disposal to optimize and improve this metric, will my startup do better the next time we measure this?

Most entrepreneurs initially measure everything or nothing at all. Operating from gut (measuring nothing) is as bad as operating with lots of useless data (measuring everything). When you measure everything (or as much as you can), you tend to get overwhelmed and try to optimize everything.

Which is why most every accelerator program I know of, advises entrepreneurs to pick one metric and focus on them.

Without trying to give you a list of metrics that you should consider, I thought I should outline the thinking process you should follow to come up with the metric you should care about, measure and track.

1. Leading vs. Lagging metrics: Metrics fall into multiple segments, but the are usually leading vs. lagging. A leading indicator tells you what’s going to happen to your business, while a lagging metric tells you what happened. For example, usage of your product with customers is a leading indicator, but revenue is a lagging indicator.

2. Financial vs. Operational metrics: A financial metric, as it implies, affect your top or bottom line. An operational metric is useful to track and improve your efficiency. For example, Customer Acquisition Cost (CAC) is a financial metric, but Conversion Rate is an operational metric.

3.  Actionable vs. Reporting metrics: An actionable metric is useful to change behavior. A reporting metric is useful to disseminate among key stakeholders. For example, % of candidates who applied for any position is  a reporting metric, % of those who you interviewed is actionable. You can change an actionable metric and it will affect quality. Change a reporting metric and it will look good, but not affect the way you operate much.

4. Primary vs. Derived metrics: Primary metrics are measured directly, derived are determined by a formula or combination of 2 or more primary metrics. For example, number of visitors to your website is a primary metric, visitor engagement, i.e. # of visitors and time spent on site is a derived metric.

5. Absolute vs. Relative. Measuring absolute numbers for a metric tell you where you are at a point in time, but a relative metric give you a sense of the metric over time. For example, # of open bugs is absolute, Growth in # of  blocking bugs is relative.

Given the segmentation and type of metrics, and that they serve different purposes, if I had to choose one metric, I’d choose:

A metric that’s leading, operational, actionable, derived and relative until I raise my series A funding.

You need to choose only one metric and it will be hard to pick one without others, but I’d highly recommend you do this exercise and paste the metric everywhere and communicate it constantly, so you can have everyone align around it.

One of my companies had a bell that they rigged up that would constantly ring when the metric turned south. The pain of listening to that bell was so bad that the entire company would rally around it to “switch the bell off”.

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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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