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10.15.18

Dear Founder

Dear Founder

W
HAT BEGAN AS a project to provide guidance to a select group of founders in the Webb Investment Network has been expanded and offered to founders of all types and those who need to have a founder’s mindset. The result is Dear Founder written by Maynard Webb with the help of Carlye Adler.

Maynard Webb is a Silicon Valley veteran and investor. Behind all of these letters is real-world experience from his days at IBM, eBay, Yahoo, LiveOps, Gateway, Bay Networks, and Quantum. They are organized to follow the trajectory of a company’s life cycle from getting started, getting to relevance, getting to scale, to finally leaving a legacy.

Being a founder is complicated, and with each step in the life cycle, the success stories become fewer and fewer. Webb’s wish is that these letters will help you and your team through the tough issues that most founders inevitably face.

Too often, Webb finds that founders set the bar too low. It’s uninspiring, and the company doesn’t “achieve the destiny it’s aiming for.” “I’ve learned,” says Webb, “that it is better to aim very high and not quite achieve perfection than to nail every goal and deliver mediocrity.” He encourages, “We are all capable of more than we think we are. Dream big, and execute bigger. If you are willing to dream and then work hard and execute well, you can achieve more than you ever imagined.”

Fundraising while exhausting, can make you better. “Fundraising is a lot like sales, only this time you’re not selling a product but rather shares in your company…. It can offer a window of self-reflection and a chance to tighten your story and focus on the important drivers of your business.”

There are many letters on the nuts and bolts of growing a business, but not surprisingly, many of the letters deal with the human side. It’s all about people. Here are some excerpts from several of the letters:

When You Need to Delegate

“Effective delegation means that you know that the task/project will get done with the results that you expect. At the outset, this means that you have to:

“Assess the capability and willingness of the team to do the task. Often, people will volunteer for a cool assignment, but can/will they really do it?

“Communicate what success looks like to the people you are delegating to. What is the timeline, quality, etc.?

“Ensure they know that if they encounter problems, you are there to guide them. Overall, you are still accountable for the results. Delegation is not abdication.

“Establish checkpoints to monitor progress, so you don’t get any nasty surprises at the end.

“When the team delivers, celebrate their success.

“The more confidence you have in a team or person, the less structure you need to make delegation work.”

When You Are Overwhelmed

“The important thing is to realize that it is a momentary state. By shifting into action, you can get rid of this uncomfortable feeling. Once I realize that I am feeling overwhelmed, I don’t need to actually fix everything to get rid of the overwhelming feeling; I just need a plan that I believe in and that I can start executing.”

When You Are Confusing Hubris with Boldness

“Of course everybody that comes in thinks they have a winning strategy, but when someone truly has conviction, it shows. How? It’s when someone can crisply articulate the vision, the value proposition, the market, and the potential. They have clarity on what their next steps are and what will be done with the money. Rather than downplay competitors as dumb and naïve, they explain what the strengths of each are and why these strengths will make the difference for them to outcompete this new startup.

“Here’s the one thing that signals a bold attitude that might be more counterintuitive: being secure enough to identify the parade of horrible things that can go wrong.

When You’re Accused of Working Too Much

“In staring a company, the unfortunate reality is that there’s no such thing as balance. Taking an idea to greatness requires extreme—Herculean—efforts.

“Sometimes these trade-offs will be worth the cost, and other times they won’t be. If they are not, don’t commit to doing your job halfway.

“Our work and personal lives often collide, and they will only continue to do so. The best way to make it all work is not to silo off these distinct parts, but to weave them together into a custom tapestry. If you do that, and if you are truly doing what you love, it trumps the desire for balance and achieves something better, something magical.”

When You Self-Impose Limits

“When you create limits that don’t really exist, you are justifying where you are. And where you are is never as great as where you could be.

“Generally we put more limits on ourselves than any outside force ever can.

“If there is a recipe for success, I believe that it is this: Get out of defense mode and go into wonder mode.

When You Receive Public Criticism

“I’ve come to realize that getting input—good or bad—is a blessing. It gives you invaluable information on how you are doing, and more importantly, how you can do better.

“So what do you do when you’re on the receiving end of critical reviews or negative comments? First of all, congrats—this is validation that people care about what you’re doing.”

Other letters include:

When you are selecting a co-founder
When nobody wants to give you money
When everyone wants to invest
When you need to spend your money wisely
When you need to figure out compensation for your sales team
When you need to know who owns what
When you need to have an open door
When you need to build a great board
When your first key hire leaves
When no one is excited to be here
When you need to deal with poor performers
When you have to face that your startup is failing
When you need to pick your battles
When you need to improve execution
When you need to scale
When you have just missed your quarter
When the board says they are replacing you as CEO
When you have a big payday

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Of Related Interest:
  Rebooting Work: How to Make Work— Work for You

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Posted by Michael McKinney at 12:07 AM
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