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CEO

Career Advice

The choice we make to be loyal, or not

September 14, 2021

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 taught you what they know, or maybe you believe demonstrating loyalty to them will give you a payback. Or in the simple case you just really like them and want to support or protect them.

Similarly, the people you work with will choose whether to be loyal to you or not, primarily based on your behavior. They will each make a decision as to whether you are worth their loyalty or not.

Loyalty is different from friendship – you may not mingle your families or hang out after work – but it outlasts any one job. It may well outlast your career.  I was recently contacted by a former colleague who asked me for help with an ugly situation. Even though we have not worked together for 20 years, or spoken for 10 years, I did not hesitate because I still feel loyal to him.

It can backfire when it is too strong though – when it blinds you to an employee’s performance issues or slows down a difficult decision. For example, the case when a CEO won’t move on an executive that is the wrong person for the job because she is too loyal to her team members. CEOs are usually too slow to fire people; by the time they make the decision it is often at least 6 months too late. I have watched a board unable to remove a failing CEO because they had worked with him for so long; I have seen a CEO removed from his job for not being willing to act on an executive he was too loyal to that was pulling the company down.

Loyalty can put you in a no-win situation. Do you betray a loyal colleague when they lie? When someone you are loyal to is bending the truth to get to an end result, and you know it, and you are asked for the whole truth? Do you reveal the whole truth and expose the colleague you are loyal to? Do you keep quiet, or find a way to avoid the confrontation? I was young when I was put in this situation and I still feel internal conflict when I think about the choice I made to back my boss and help him make the sale on the terms he wanted rather than expose his manipulation of the facts.

But on the flip side, loyalty is powerful and important in tough business situations. When you are growing a business and there is a crisis (we see something every few years… 9/11, 2008, Covid-19) you can take more risk and face down more dragons if you are confident that the people you are working will stick with you, and your plans, through the crisis. When you are personally under attack from a competitor, or a co-founder, or a colleague knowing who you can count on to support you and follow through on their responsibilities no matter what makes all the difference in the world and can allow you to stay focused on the challenge right in front of you.

Loyalty is tested in difficult situations and it is tested over time. It still surprises me to learn who of my former employees and colleagues are still loyal to me today. Surprises and humbles me. And I am hurt by those who I thought were loyal and then showed over time they were not.

But it is a choice. You can decide who you will be loyal to. Are you conscious of who your choices are?

Photo: A loyal Italian soccer fan in Florence © 2021 Penny Herscher

Leadership

Stop focusing on your startup valuation!

June 17, 2020

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 valuation, like a stock price, is a reflection of the perceived value of your company at the moment in time when you are raising money. There will be times when the startup market is hot and you can command more, there will be times when it has cooled because of an economic downturn, or a global pandemic, and your valuation will be lower. Or the market your idea is in is hot, or not.

What matters more than valuation is: Are you getting the right amount of money to give your idea life? Think about the next one, or two, major milestones you need to achieve to prove your idea will work and is scalable. Then figure out how much money you need to raise to get 90-120 days past the critical proof point. Add to that number to allow for the unexpected and that is how much you must raise. Once you have that you are looking for an investing partner who shares you vision and will be with you on the journey.

The other consideration is what value opportunity are you creating for your employees? The higher the valuation on funding the higher their option strike price and so the less money they will make when you finally reach liquidity. Now, if your company is a rocket ship, the difference between an option price of 50 cents or a dollar doesn’t matter, but at a later stage the difference can matter and when there is a preference stack on your company getting greedy can wipe out your employees’ opportunity. We’ve seen this happen with unicorns who achieved huge valuations only to have them come down dramatically on sale or IPO. So don’t lose sight of the need to make your employees money as well as yourself.

I have written before that all venture capital firms are not equal. Some are good, some are awful. The same applies to angels btw. I have seen short-sighted angels do more damage to young companies and entrepreneurs than I would have thought possible by focusing on their cut and not the long term health of the company.

It is more important to a) raise the money you need and b) find a long term investing partner than finding the best possible valuation. If you own 40% of your company but it is worth $20M at the end you have short changed yourself and the impact your idea can have if, instead, you own 15% and it is worth $1B.

Photo: Stone canon balls Jordan © 2017 Penny Herscher

Career Advice

So you want to raise money – chose your investor carefully

October 27, 2018

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 was delighted that the entrepreneur I was coaching also brought up how to assess the quality of the investors. The quality of the firm and the individual. She’d had a bad experience in the past and simply did not want to have a poor quality individual in her deal.

Many entrepreneurs never realize how important this question is: all money is green but it is not all equally valuable. Investors, like human beings, come in all styles and since building a company is a marathon not a sprint you want to be running with someone who is enjoyable to be with and who will help you win the race.

First, 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 you don’t get rich in the startup world by trying to get rich, you get rich by building something) and it’s very important that your investors want you to change the world too. There are many, many tough moments of truth when building a company, and none more so than when you get an offer for your company before you think you are ready – before you have built the strategy and value that you believe is possible. That moment is when you find out whether your investor truly shared your vision on how to change the world or was just telling you he did.

It’s also important to pick a partner who can do heavy lifting for you when you need it. Great venture firms have a rich, deep network to help you recruit, develop partnerships, manage sticky HR issues and even find office space.

Avoid the money based VC (often a former investment banker) who’s motivated by running a portfolio, who wants to tell you what to do but has never done it himself. Find someone who walks the talk and builds great companies. Find a former entrepreneur who has really done it him or herself. If you can, find a VC who has been doing it for more than 10 years and has a great track record – and talk to their CEOs – or find one who’s been a CEO, built a good company and taken it public. All this is visible on their web bios.

And pick someone you enjoy being with. Most companies take many years to mature and if you are going to meet with your board a couple of times a quarter for 5 years it certainly makes the journey more fun if you enjoy interacting with them.

Sadly there are many entitled, think-their-shit-doesn’t-stink VCs in Silicon Valley. I could fill a book of stories of men who think they are rich because they are smart and that they don’t have to be courteous or helpful. Who are openly rude, dismissive and condescending. For comic relief – one of my most bizarre meetings was with a young VC whose firm had been in early at Google and he spent the whole meeting behind his desk checking the Google stock price and telling me how much money he had made. He was not the partner in the deal, just in the partnership, and yet he still thought it was all about him and I should be impressed!

But at the same time there are plenty of men, and women, who truly love working with entrepreneurs and have a very healthy respect for how hard building a company is. The challenge is you may have to kiss a lot of frogs to find your investing prince or princess. So manage your time and do your research up front.

Of course, in the end, you do need to get funded and you may need to take what you can get, but if you have the chance to be selective, the right investor is more important than the highest valuation because you’ll build a better company, have a stronger chance to change the world and make more money in the long run with the right partner.

Photo: Valetta, Malta © 2018 Penny Herscher

Career Advice

How does your investor make money?

August 2, 2018

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 than your friends and family will give you a useful amount of money they are going to want to know how much return they are going to make, and over what period of time. Unless you are a former founder with an amazing track record, or flat out lucky (and you can’t plan for luck) you will need to be able to explain the following:

  • what the size of the market is for your idea – who buys what/when/why
  • how you bring your idea to that market and how much money you make over time (your best stab at your P&L over the next 3-5 years)
  • what your idea/prototype/beta is worth now (i.e. if you want to raise $1M and you only want to give away 10% of your company then you have to justify why your current company is worth $10M today)
  • how the value of your company grows over time and possible exits – why is it IPOable at some future date or who might buy it?

You don’t necessarily have to have slides for all of this because the first thing you need to do is hook an investor on your idea but if they bite and start to ask how you see your revenue and value developing you’d better have enough of an answer to get into a good discussion. Don’t be intimidated. Remember the investor does not know more than you do about your idea (even if they act as if they do), and whatever you say will not be what happens (reality has a way of messing with even the very best of plans) but you need to have thought about how you’ll make money and be able to engage the potential investor in a discussion.

Eventually you’ll need to be able to make the argument for how revenue grows, how much cash you need to get to cash flow breakeven (i.e. self sustainable) and what the company will be worth in the future when you do. And the great VCs, if they are intrigued, will then dig in and help you figure out your first business plan and how to value your initial round.

Photo: Dante’s tomb, Ravenna Italy © 2018 Penny Herscher

Leadership

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

April 24, 2018

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 vision. Once the company is off the ground courage is needed for the big moves that set the future, and because they are big moves they are inherently risky.

Take a look at your company, or the company you are thinking of joining, and look for the signs of courage in the CEO. For example:

Buying a large company, spending a billion dollars or more takes real guts. It has to be for strategic reasons, product reasons, and make sense to the shareholder. But no matter how compelling the strategic and financial argument the CEO knows so many things can go wrong during or after the transaction and in the end it is the CEO who will take the blame if they do. The board will question (that’s their job) and weak boards won’t want to take the risk – it’s easier to do nothing. So they will look to the CEO for the final courage to make the move. I do, however, think M&A of small companies doesn’t take much courage. “Tuck-ins” as corp dev teams like to call them can be justified on financial terms and, unless you greatly over pay, don’t incur much risk. But the big ones take courage and conviction.

Changing  the business model – for example moving software to the cloud. The courageous CEO takes a stand and makes it happen. He tells the shareholders what he’s doing and how many quarters it is going to take and then he leads the organization to make the change happen fast. Transitioning a software business from a perpetual, on-premise licensing model to a subscription model in the cloud is really hard because it always causes the stock to drop in the near term (although it will recover and be stronger if you execute). There are always a thousand reasons why to wait – “customers are not asking, we’re not ready, our shareholders won’t tolerate it” – and it’s true that revenue drops and margins take a hit for 8-12 quarters. It takes courage to lead your employees and shareholders through the transition and to stay the course as your stock suffers – but in the end you have much more resilient revenue and higher multiples.

When an industry is going through a major transition does the CEO face it with courage and double down to get ahead of the change or stick her head in the sand? The automotive industry is facing its biggest challenge ever with the rapid adoption of electric vehicles, ride-sharing and with Level 4 autonomous driving only a few years away. Ten years from now we’ll look back and see which CEOs had the vision and courage to lead their auto companies into the new world and which didn’t, because some car companies will no longer exist. But in the short term pouring investment into new technologies to get and stay ahead of the rapid rate of change is a huge decision. At Faurecia (a $20B auto company where I am on the board) the employees are not confused. The CEO is direct with them about the need for tremendous change and he is showing significant courage investing and leading them through it.

Firing non-performing executives is another area that takes courage. When an executive is weak the employees know it. But so often CEOs are slow to act. There is an old adage that by the time you know you should fire someone you are probably already 6 months too late. So why then will a CEO know he has an executive that is not cutting it and yet wait? Because firing people is hard and carries the risk that you will not hire well – maybe you’ll make a mistake and hire someone who is no better? Or maybe you are just so busy you can’t face putting the time in to do the search for a replacement? Firing a B-player senior executive is risky but so necessary because their department/group/division will be populated with B players, not A players and so probably not as competitive or effective as they need to be.

And finally a more subtle one. The courageous CEO is accessible. He will answer emails directly from employees rather than hiding behind an admin. He’ll walk the halls and factory floor to really listen to what employees think. He won’t stay behind glass in mahogany row and limousines, he’ll make sure his customers and his managers can find him, talk to him, and most importantly bring him bad news without him shooting the messenger. It’s a subtle form of courage to truly listen, but it’s courage none the less.

Can you put yourself in your CEOs shoes? Do you see courage and the willingness to take risk to grow the company, to listen, to make the big moves? Take a good look and then make your own assessment of whether your CEO is going to win. And whether you want to be one yourself one day.

Photo: Florence © 2018 Penny Herscher

Leadership

5 Pros and Cons of Being CEO of Your Company

January 27, 2015 Leave a comment
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 around it’s likely more money than you ever dreamed of. But for most CEOs, the truth is not in the extremes.
It’s in the middle.

So before you decide to be the CEO of the company you want to create, here are a few Pros and Cons to consider first:

1. Pro: You decide the strategy and what’s important. When you are CEO you are ultimately responsible for the strategy: What to build? How to get to market? Where to focus? You get to put your ideas into action and test if they work. Then, when they do succeed, the sense of satisfaction is unbeatable. If you are the technical founder, and command the respect of those people around you, you also won’t have to hear much disagreement. People are following you because they believe in your vision and your strategy.

Con: You’ll work harder than you have ever worked in your life. It’s true not all CEOs are working on overdrive but when you’re trying to get a
company off the ground, there are always more mission critical things you need to do that require more hours than there are in the actual day. Look forward to the necessary red-eye flight you need to take to close a deal. The time pressure will seem worse than your college finals did and prepare for this pace to go on for years. Keeping physically fit with exercise will become a requirement just to survive the exhausting workload.

2. Pro: It’s an ego trip. It’s hard to be CEO unless you have a serious ego. Not that you have to be a jerk, but exuding confidence will ensure that people can look to you to lead them. In that sense, then yes, it’s an ego trip. Which means that, if you are already seriously thinking of becoming the CEO of your startup, then you probably have that necessary ego to both embrace and enjoy it.

Con: You’ll be lonelier than you’ve ever been in your life. That cliche “the buck stops with you” is absolutely true when you are CEO. There is no one to turn to if you have to make a hard decision. Your board is there to give you advice, but they are not going to tell you what to do. Your team is there to provide counsel and debate with you but in the end, they’ll look to you to make the difficult decisions. And there’s no one you can talk to. It’s unfair to burden your friends and family with these work related stresses. It’s you and the wall (or in my case the dog) talking it out sometimes.

3. Pro: You get to hire your team. When you are CEO you get to hand pick your team. You choose the structure of the organization, and hand pick the key people you want to build the company with. You choose the skills, the personality, the experience–and they will seem to become as close to you as your family. Building teams is a wonderful experience–and the best trait of a successful company comes down to the talent.

Con: You’re the one who has to let people go. It’s hard to consistently hire great talent which means sometimes you’ll make mistakes. You’ll hire a VP of Sales who looks and sounds good, but can’t build out a team themselves (think of Yahoo’s spectacular failure recently hiring and then firing of Henrique de Castro). There may also be a time when you may really like an employee but who struggles to consistently perform. When you are the CEO there is no ducking the responsibility of firing the people who have to go, and striving to do it with respect and kindness is an art form.

4. Pro: Customers rely on you to solve their problems. Most great ideas come from trying to solve a problem for someone. In the enterprise world, you’re most likely solving a business problem for another company. You could be putting a critical process in the cloud, so it’s more cost effective, or automating a solution for a time consuming technology problem. It’s a rewarding feeling to know you helped customer’s solve problems and improve their overall business–and of course make money for both of you in the end.

Con: Customers can jerk you around. A former CEO of a software company with $1B in revenue once told me he quit, in the end, because of some of his customers. They’d hold deals until the last day of the quarter, and then force him to drive the price down to get the deal done. After 10 years of building his company and providing solutions for countless customers, he was overwhelmed with the lack of respect his customer’s gave to his business. As you’ll find, this is not always the case and there will be times you are providing value to your customer but professional patience and just ‘sucking it up’ will still be required.

5. Pro: You set the culture for your company. And this many especially appeal to you if you are sick of the Silicon Valley bro culture. Many people spend 8-10 hours a day at work. And all this time should be joyful. Why work for a company, if the culture is not enjoyable? So as CEO, one of the most important responsibilities you have is to set the right culture of the company with the actions you do every day and not just what you say. Great CEOs, like Reed Hastings of Netflix, make this the centerpiece of their leadership. They focus on the areas they believe create a successful company and a positive environment to work, which in turn assists in better recruitment, and increasing their impact with the community.

Con: It’s your company. Well, is that a pro, or a con? You’ll find it depends on the day. Some days you’re so proud of the solutions your team provides that you could burst. But this will not be every day, definitely not every day.

So, if you want to be the CEO of your company then brace yourself. It’s a wonderful experience, and can be a thrilling ride, but it’s a roller coaster with many ups and downs. Maybe write down why you want it before you start, so that on the dark days you can remind yourself why you are doing it. Me? It was about creating a great culture.