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Avoidable Founder Mistakes

June 22, 2021

“If you are not embarrassed by the first version of your product, you’ve launched too late.”

– Reid Hoffman, LinkedIn co-founder 

Launching a startup is a risky venture. It’s been said that 90 percent of startups fail. The statistic is not surprising considering the amount of effort, time, and money it takes to build a company from the ground up.

Many founders, especially first-time founders, inevitably make mistakes. Some more costly than others and some which could have been avoided in the first place. Mistakes are hard and unforgiving in general, but especially in the startup space. 

As founders look to accelerate their startup, it can be easy to put the blinders on and ignore key issues that could slow down or stop the momentum of your startup altogether. Learn how to recognize avoidable founder mistakes and how to address them.

1. Launching in an Unfamiliar Space Instead of Sticking to What You Know

You’ve likely heard of product-market fit (which we’ll address later on), but there’s another type of fit founders should have. Technology entrepreneur and investor Alex Iskold calls it founder-market fit. The idea is that successful startups have a strong match between the founder’s expertise and the problem they are trying to solve.

Domain experiences and insights really do matter. Founders with domain expertise have the unique insights needed to understand the pressing challenges and golden opportunities to go fast and launch a successful business. 

The reality is that some founders start businesses in spaces they don’t know much about. Even Iskold mentions this is exactly what happened to him after selling his first B2B company to IBM and struggled with launching his second startup which was consumer-facing. 

There’s a flipside, it is possible to launch a successful company without having founder-market fit as seen with Convoy, a disruptor and leader in the digital supply-chain revolution, whose co-founders both worked at Amazon. They made it possible by bringing on other leaders who were experts in their respective fields.

2. Underestimating the Value of the Right Co-Founder

The right co-founder for your startup is critical. You need someone who compliments your strengths. Choosing the wrong co-founder could become a costly mistake for your startup. 

As a founder, you’ve learned to accept you don’t know all the answers to every question. You have blind spots too. You are going to make mistakes but the key is to limit the mistakes while mitigating the impact of these mistakes. That’s why having the right co-founder who brings in new perspectives and experience is key to failing fast and winning even faster.

Finding the perfect co-founder is like finding the perfect partner in a long-term relationship. There is a lot of blood, sweat, and tears involved. You want to make sure you find someone who can speak directly and honestly with you, especially during those pivotal business decisions and times of conflict. You want someone who understands your needs and you theirs. You want someone who can own up to their part of the company’s success as well as failures. 
Garry Tan knows all too well about co-founder conflict as a co-founder of Posterous (acquired by Twitter). He directly puts it, “I learned the hard way that if you haven’t prepared for conflict in your co-founder relationship, you’ll be at each other’s throats right at the moment when you most need to be working well together.”  

3. Waiting for the Perfect Product to Launch

“Perfection is the enemy of progress.” A quote attributed to Winston Churchill but is as relevant today especially in the startup scene. Nothing kills progress more than perfection. Perfectionism can kill productivity, ideas, momentum, and potentially your new startup. 

Don’t spend time perfecting an unproven product, launch as quickly as possible. 

Understand what the market is looking for and launch with the minimum viable product. The immediate market feedback will be the invaluable input needed to modify, pivot, and update the business. Tangible and actionable actions based on real market feedback versus the perceived feedback that happens in the space between four walls. By launching an imperfect product, you’ll have created a continuous feedback loop on how close you’re getting to product-market fit.

This is the approach Mary Biggins took when she launched her growing startup MealPal. “Getting it to market quickly (and with some rough edges) was way more valuable than waiting 6 more weeks to launch the perfect version of the product. You don’t really start learning until you are getting feedback from real users.”

As a founder, you want to see your startup succeed and not be part of a statistic. Some mistakes are hard to recover from but some are also avoidable. Remember to stick to what you know, find a co-founder who complements your strengths, and get real market feedback sooner rather than later.

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Nail Your Customer Discovery – Sean Sternbach

August 12, 2020

This article will highlight ways to start validating your startup idea. It starts by doing customer discovery.

Two years ago, Sarah, an engineer at Microsoft decided to take the plunge building her startup.  She quit her day job and then spent months building her product. The day came for her to launch the product into the market and when she did, no one wanted to use it.  Ouch.  Too often talented engineers build products without talking to customers first.  They wonder why potential customers do not want to use what they built.  The way to solve this is to start by doing customer discovery before writing a line of code.

Without getting technical, customer discovery is about talking to people and learning about their pain points with the intent to validate (or invalidate) your assumptions.  This is called primary research.  There are many ways to approach this process, and to set yourself up for success you should have the following steps in place beforehand:

Define your personas.  Start out by hypothesizing who will be your target customer. Personas describe characteristics of your target customers and you will most likely have several of these for your company.  If one persona is an engineering manager working in a tech company, you may highlight various aspects of her job, what motivates her, team size, and the type of company she works for.  If you are offering an e-commerce product, you may have more characteristics around user demographics.  You may not know who your target personas are, but you should start hypothesizing and iterating on this.

Once you’ve thought through the type of people to talk with, write your customer discovery questions down on paper.  With practice, you will refine this process.   Your questions (and personas) may change, but it is important to write them down.

Set up a CRM (this can be a Google sheet) to track everyone you are talking to as well as the feedback they provide you.

I often get asked how many customer interviews are enough before I can start building my product.  There is no magic number but if you have to ask the question you haven’t done enough.  Once you have a recognizable pattern of the pain your interviewees are experiencing you are on to something.  An example of this would be if the majority of people you talk to offer to pay you on the spot to fix the problem they are having.  If you are not hearing about a repeatable pain from everyone you are talking to, you should continue conducting customer discovery interviews.  

I’ve seen successful startups do more than 200 interviews before they were confident to build product and take institutional capital.  One of these companies is Iteratively.  Iteratively’s co-founder, Patrick Thompson, said, “Customer discovery was the single most important thing we did when starting Iteratively. It helped us identify a problem worth solving, validate our solution, find our early customers and close funding. It’s the single most important thing for founders to spend their time on.” 

Keep in mind, they made micro-pivots to hone in on the right target customer, which meant more customer interviews.  This was due to not hearing enough signal about the pain – and all of this was done before writing a single line of code.   

Other founders got lucky and received a strong signal about the pain with their first 25+ interviews.  No matter which group you fall into, you should know who your target customer is better than anyone else.  This will help you identify more customers that fit your mold and talk intelligently about them with potential investors.

Going through the customer discovery process will help investors know you did your homework.  They need to know that you know your target customer better than anyone.  You should be a SME on your customer and their pain point(s).  You should know the personas inside-out.  

For me, this means conducting 50 or more customer discovery interviews.  My logic for this number is that if you cannot find 50 people with this pain, how will you build a multi-million (or billion) dollar company with thousands of people using your product?  The best founders I’ve seen understand how to be scrappy, and get in front of potential customers to validate the pain.

Here are some things you can do to find more people to conduct customer discovery interviews.  The fastest way to do this is to identify communities that fit your personas.  The ones that I’ve seen work the great are below:

Slack groups

Reddit channels

Facebook groups and other social channels

Trade associations

Ask mentors, advisors, etc., for introductions

Meetup Groups

Google

No matter what, customer discovery interviews never stop.  Your customers continue to evolve, and hopefully your company evolves with them and that means continuously learning from your customers.  Here are a few additional resources to help you with your customer discovery:

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