Startups Archives - The Grassy Road

The challenge of FOMO in your career

FOMO today is typically about missing out on something cool – someone’s vacation on Instagram, a restaurant they ate at, their new car. Merriam-Webster defines it as “fear of missing out : fear of not being included in something (such as an interesting or enjoyable activity) that others are experiencing”. But in the rat race of our modern careers FOMO happens around your choice of profession too. I see this many times when coaching people at transition points in their careers. You’re working at a large company (in a good [...]

By Penny Herscher|2025-01-24T08:49:08-08:00January 23, 2025|Career Advice|Comments Off

Startup or large corporate – which is best for you?

Everyone has an opinion of whether you should work for big companies or small, startup or corporate, but the answer is very personal. I was coaching a group earlier this week and the question came up as "I am working for a startup but everyone is telling me I should go work for a big corporate now for my resume - what do you think?" I believe there is no right way, no right answer. But there are dimensions to consider as you map out your next step. Are you [...]

By Penny Herscher|2019-01-04T09:57:47-08:00November 16, 2018|Career Advice|Comments Off

Managing the switchbacks of your career

A successful career is rarely a straight line up the slope. It is so often a weaving up through experiences and it's important to recognize how and when to weave. I did a coaching session yesterday where just this question came up. This time the individual had years of engineering, both as a stellar software engineer and also as a manager and can feel he wants to do more - can do more - and knows he needs to broaden his skillset. I have a handful of principles which can [...]

By Penny Herscher|2019-01-04T10:01:14-08:00July 18, 2018|Career Advice|Comments Off

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

Startups and adrenaline are a potent mix

Fred Wilson's post a few days ago "Starting is Easy, Finishing is Hard" speaks to the grind going on for many tech startups today. He says the easy exit days feel as if they have gone and for many it is taking raw tenacity to finish. And he's right. When you are the CEO or in the founding team of a startup the years are long. It feels as if it will take forever to get to the next stage of product, or growth, or market development. But the days [...]

By Penny Herscher|2017-12-09T19:51:05-08:00April 26, 2017|Leadership|0 Comments

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 new self-help book for entrepreneurs “Build Something Great!

Thinking of starting your own company... or you're already in it? There's a fun new self-help book out for entrepreneurs called "Build Something Great!: Fifty Best Tips for High-Tech Startups" that is a must read and excellent reference book for anyone wanting to win the first time. Written by two of the Simplex founders, professors Resve Saleh and David Overhauser, it boils down valuable startup advice into 50 tips on how to build your own successful venture. And yes, I admit I'm biased since Resve and David hired me to [...]

By Penny Herscher|2017-12-13T08:40:51-08:00February 4, 2016|Leadership|0 Comments

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

Venture Capital Is Not All Equal

Like people, VCs come in all styles, so here are 5 characteristics to consider as you interview potential investors.If you want to raise venture capital to fund your new company and your great idea, plan out your vetting process first, because all VCs are not the same. Some are really helpful, but some are horrible and damaging to your company. Pick someone who has the same Vision and Values as you. You are (hopefully) in your venture because you believe you can change the world (if you are doing it to get rich, stop now, because [...]

By Penny Herscher|2020-06-17T08:38:54-07:00December 16, 2014|Leadership|0 Comments