entrepreneur Archives - The Grassy Road

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

Five practices you can learn so that “I told you so” is a gift

Does it irritate you when someone says “I told you so” to you? You’d be quite normal if it does. There is nothing quite as annoying as having a know-it-all tell you that they knew better than you all along and you did not listen. And yet, if you can check your ego, and if he did actually tell you so, then you’ve been missing a gift. Of course, this only makes sense if you are getting advice from someone who is often right, and who cares about you, otherwise [...]

By Penny Herscher|2019-01-04T10:10:47-08:00August 11, 2017|Career Advice|0 Comments

5 reasons it’s critical to truly understand your P&L

In the last month I have had the experience of three small business leaders talking to me about their P&L in moment-in-time terms. Something like this... for this quarter (or this year) we'll make $X, we spend $Y less than I thought so we're $Z ahead. Usually followed by why $X and $Z are so great, and how they'll spend those extra dollars they are ahead, or why their company is successful as a result. Naive. Unless you have a steady business that has been the same for a while, [...]

By Penny Herscher|2019-01-04T10:12:19-08:00July 20, 2017|Leadership|0 Comments

The importance of being humble

Photo: At the Jordan river where Christ was baptized and Israeli and Jordanian soldiers watch each other, guns cocked We’ve all met this person in our professional lives. Smart but self-absorbed, in love with their own success so far, or with the self-importance of their title, or the size of their business, or how attractive they are. Executives who are so used to everyone catering to their every need that they forget to be courteous. VCs who are so used to entrepreneurs beating down their doors they forget to be kind (or [...]

By Penny Herscher|2017-12-07T10:33:34-08:00July 16, 2017|Leadership|1 Comment

How 2016 rocked my world as I talked with women entrepreneurs

I am more convinced than ever that there is a bright future for women entrepreneurs and 2016 proved it to me! I stepped back from being a full time CEO a little more than a year ago. It was time, for family reasons, and I set out to change my life. I still work (I serve on two public company boards) but I decided to spend a great deal more time with my father and my family than I have ever been able to do before, and to prioritize my [...]

By Penny Herscher|2017-12-10T12:01:17-08:00January 4, 2017|My Personal Journey|0 Comments

The difference between being right and getting the right answer

Entrepreneurs can be a hard headed lot. It takes courage, determination, a lot of luck, and sometimes just old fashioned, bull-headed persistence to create a company but as a result entrepreneurs don't always listen well.But even if you know you resemble this description, ask yourself - is it more important for you to get to the right answer, or to be right? You want to be right because your team wants to follow someone who knows what to do. You want to be right because it's more efficient, and it [...]

By Penny Herscher|2017-12-10T12:12:13-08:00October 29, 2016|Leadership|0 Comments

Why you need a CEO on your board when you are the CEO

One of the first decisions an entrepreneur needs to make once she has raised money for her great new idea is to build a board. This is a conscious act. Yes, your investors probably have board seats, at least the lead investor will. If your investors are angels maybe 2 or 3 of them have demanded to be on your board. But beyond this crew you owe it to yourself to step back and think about who do you want on your board to help you build your company. It [...]

By Penny Herscher|2020-01-09T11:24:55-08:00July 20, 2016|Boards, Leadership|0 Comments

Who needs sleep anyway

Sleep. What a concept. As an entrepreneur it's more rare than cash, and harder to come by. As Mark Suster wrote in his recent blog post about Entrepreneurshit "It’s 4.50am. Sunday morning. And I couldn’t sleep. I have much on my mind since I just returned from a week on the road. 5 days. 3 cities." Most nights I lie awake for 2-3 hours in the night. The gerbils running on the treadmills in my mind never stop. Problems. Opportunities. Equations. Spreadsheets. People. Endlessly running. Until recently I worried about [...]

By Penny Herscher|2017-12-03T02:44:32-08:00November 27, 2012|Leadership|0 Comments

The Passion of the Entrepreneur

"Collyer's mother: Beware of passion Hester. It always leads to something ugly. Hester Collyer: What would you replace it with? Collyer's mother: A guarded enthusiasm. It's safer." Classic lines from The Deep Blue Sea, and the sentiment of the England I grew up in. Passion, while interesting in poets, was a sign of weak character. One should always maintain an even keel, and in times of trial, a stiff upper lip. But when you're building a company, or developing a new product, or growing a team, passion is essential. It's [...]

By Penny Herscher|2017-12-06T16:52:53-08:00October 23, 2012|Career Advice|0 Comments