CEO Archives - The Grassy Road

The choice we make to be loyal, or not

Is loyalty a good thing – or is it a dirty word? Depends on the context – politics, business, your family? But when talking about professional loyalty it can be a double-edged sword. Fundamentally to be loyal to another person is a choice you make. You may have several different reasons to choose to be loyal. You may admire the person – their intellect, their effectiveness, their values. You may be grateful to them for helping you through a tough situation. Maybe they made you money, or promoted you and [...]

By Penny Herscher|2021-09-15T05:56:09-07:00September 14, 2021|Career Advice|Comments Off

Stop focusing on your startup valuation!

It never ceases to amaze me how hung up entrepreneurs get on the valuation of their startup as they raise money. It came up in a coaching session again yesterday. In the abstract yes, valuation matters. It tells you how much of your company you are going to sell in order to raise money. It sets a baseline for you which you will (hopefully) exceed on your next raise. It's a validation that your work has value. But it is NOT a measure of pride, or ego, or size. Your [...]

By Penny Herscher|2020-06-17T11:18:17-07:00June 17, 2020|Leadership|Comments Off

So you want to raise money – chose your investor carefully

At least once a week I take a call, or a coffee, with an entrepreneur who wants advice on how to raise money. We talk about her product and market, the stage of her business, how good is her story and what her vision is. And then we talk about the tactics of raising money. How to get a warm intro to reputable investors, how to think about angel vs. seed vs. venture, how much to raise, what a strong pitch looks like - the usual tactical coaching. Yesterday I [...]

By Penny Herscher|2019-01-04T09:59:20-08:00October 27, 2018|Career Advice|Comments Off

How does your investor make money?

So you want someone to give you $100,000? $1,000,000? How does that person or firm make money? Too often I review business plans which have a great idea, a huge market, but no viable business plan that explains how the investor makes a return. I saw two this week like this (one in the US, one in Israel). Terrific technology ideas, potentially large markets, enthusiastic smart young teams but no P&L, no future financial plan and no discussion of current valuation, or even readiness to discuss it. Before someone other [...]

By Penny Herscher|2019-01-04T10:00:25-08:00August 2, 2018|Career Advice|Comments Off

Winning as a CEO takes courage – does your CEO have it?

It takes courage to be a great CEO and yet our world is populated with mediocre ones so how do you assess a company CEO before you chose to join his company, or whether you have the mettle to be one yourself? The evidence is there if you know where to look. It’s not just about a CEO who can give a rallying speech (although it’s fun to watch a CEO like Marc Benioff do it). It’s not just about a brilliant technical founder CEO who can talk product and [...]

By Penny Herscher|2019-01-04T10:02:33-08:00April 24, 2018|Leadership|Comments Off

5 Pros and Cons of Being CEO of Your Company

Being in the role of CEO can be terrific. You're it. You've gained the power to put your brilliant idea into practice. You're synonymous with the company for your customers, your employees and your investors. Your family is proud of you. You feel like the sky's the limit. And yet, the role is a double-edged sword. If your company is a big public company, you can possibly be looking at $10, $20, $30M+ a year. Or very easily get fired. If it's one of the handful of $1B unicorns coming out of Silicon Valley, then this time [...]

By Penny Herscher|2018-02-26T08:48:07-08:00January 27, 2015|Leadership|0 Comments