Tag: CEO

When frustration strikes, ask this simple question

Nicole Glaros2 Comments

I have sat on many boards of directors, and since many, dare I say most, have been mediocre at best, I’ve become passionate about how to make them highly functional. Because of this, I recently had a conversation with a founder CEO, let’s call him, Joe, who asked me how to get rid of a particularly problematic board member, let’s call him Alex.

“Well, I need more context. Tell me about Alex” I asked Joe, the CEO.

Joe replied, “Alex used to be an ideal board member. He read all the materials in advance, he came prepared to the meetings with thoughtful insights, and he debated appropriately. He made a handful of high-value introductions and helped me think through some major issues. Alex was one of my best board members1”. 

“But recently, Alex’s behavior changed drastically—arriving late, being combative, asking questions we covered 15 minutes ago, and spending board meetings on his phone. He yelled at me during our last meeting, making things intolerable. What’s the best way to fire him?

I responded, “Have you asked Alex if he’s okay?”

Blank stare from Joe.

“You know”, I continued, “Since Alex previously was one of your best board members, what has changed? Why is he acting this way? Have you just asked him if he’s alright?”

Joe kicked an invisible pebble with his foot and sheepishly admitted he hadn’t.

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Why your company values suck

Nicole GlarosLeave a comment

We’ve all heard how important company values are; they are the basis of the culture of our company and we spend hours upon hours writing them, agreeing on them, training on them, hiring against them, and putting them on walls. And secretly (or maybe not so secretly), we all roll our eyes and know they’re bullsh*t.

Here’s why.

Most companies put up aspirational values – ways they WANT the team to act – ways they aspire to behave. But for every minor infraction of those values, every time a leader doesn’t act in alignment with those values, it immediately discredits all of the values, all of the time. Employees immediately know the values statements are just lip service because even the leaders aren’t following them. Yet how can a leader align with an aspirational value 100% of the time? It’s impossible. I aspire never to yell at my kids, but the 314th time I’ve asked for the dirty underwear to be picked up – I’m probably yelling it.

Values aren’t something you choose. A person’s values form slowly, throughout their life, and they are reflective of how the person actually acts. Values manifest in your behaviors, not in your words. You can’t choose them from a list, you can’t ship them over to marketing for wordsmithing. A company’s lived values are reflective of the founders’ personalities and how they behave, or if the founders aren’t there anymore, the CEO and executive team’s behaviors – and rarely are they the same as the company’s stated values.

If you say transparency is a company value, and you don’t share the board deck with the employees, boom, values shot. If you claim ownership as a value, but there are 4 layers of decision approvals, boom, values shot. If you claim constant improvement as a corporate value, but have zero mechanisms for doing retros on all decisions and actions, or rarely make changes to your processes, boom, values shot. Values have to be reflective of how you actually act, not how you want to act.

That doesn’t mean you can’t have aspirational values. I think it’s phenomenal to have 2 sets of values, 3 actual values, and 3 aspirational ones. But distinguish between them so everyone knows what you’re trying to do and how it is today. Otherwise, it’s total bullsh*t.

Since the company’s values tend to reflect the founders’ or the CEO’s values, it’s important to know what those are and use those as a foundation for the company. The trick is that you as the founder probably don’t know what your values are, because it’s just in how you behave every day. But everyone else can see them. If you want to do a values exercise, try this. Brene’ Brown has a great values worksheet. Fill it out for yourself, but then ask 5-10 people closest to you to fill it out for you. Ask them what they believe your values are. Your values are likely the ones the respondents identified and overlap. Have your co-founders do this same exercise, and the 3 or so respondent-identified overlaps between the co-founders are probably the right ones.

There’s something magical that happens when the right values are identified and listed. It’s like a collective exhale. The founders and leaders are acting in integrity with the values all the time, and the rest of the team now knows how to behave. And you really can start hiring for it, promoting for it, and using it as a guide to make decisions.

Go farther together

Nicole Glaros5 Comments

If you want to go fast, go alone. If you want to go far, go together.

African Proverb

I’ve always loved this quote.

Last week, I kicked off a program for venture-backable early-stage founders in Colorado.  I have 14 CEOs participating in 2 groups that meet every other week for 3.5 hours for 6 months. This program was designed to help them go farther together and is an experiment I’m running to see whether or not the framework I’ve developed can help them move the needle on performance.

That’s 14 founders of startups who believed in what I’m trying to do, who signed up for an experiment that takes significant time and effort on their part, with no guaranteed outcome.  When I let myself think about it, it’s humbling, daunting even, and I feel so incredibly lucky and grateful to have pulled such a winning lotto ticket. 

This effort is the culmination of a lifetime of stars aligning, 20 years of professional experience, 10+ years of rumination, and 4 months of running at it as hard as I could. But really, it’s the culmination of a network of people who have helped me go far, rather than just go fast.

For this first program, huge shout out to Natty Zola, Ryan Broshar, Elyse Kent, Tyler Manley, Ingrid Alongi, Brad Bernthal, Rich Maloy, and Taylor McLemore for their referrals. And second shout out to Kirsten Suddath, Brett Jergens and the good people over at Archipelago, and Tom McGrath for hosting us – the ask was huge, and you stepped up and did it with a smile on your face. And thanks to my friend Mark Solon who reminded me to “just go do stuff” and my husband for the continual emotional support.

I’m not going to talk about the program today, rather, because I’m feeling sappy, I just wanted to take a moment to sincerely and publicly thank those who have been so helpful these last 4 months in the background. May we all have those who help us get farther than we ever could alone. 

Add value first

Nicole Glaros10 Comments

I was at an event recently where one of the sponsors took about 5 minutes to address the room, talk about his firm, what they offered, and how to reach them. 

The crowd politely clapped, as everyone usually does with sponsors, but I seriously doubt a single person from that event will reach out – not because he did anything wrong, but rather because there was no value in what he said. Having been in the event organizers’ position of relying on sponsor dollars to make the numbers work, I was bummed for all of them.  And it got me thinking about the notion of value. At Techstars, we had a word for this, it was called #GiveFirst, but in my mind, it’s not just about giving, it’s about adding value first. 

In the early days of Techstars, we didn’t yet have a lot to brag about. I could show a few logos, sure, but like any embryonic company, you’re trying to figure out anything you can say to gain credibility, to gain attention.  I remember trying to recruit companies for Techstars and David Cohen giving me the sage advice to teach people something, rather than just waving a banner.

Oh, the wisdom in that guidance. Rather than just posting about applications opening (which I did with little effect), rather than just asking every person I knew to refer companies (which I did, with little effect), rather than taking out ads (which I didn’t do because I hate ads and we didn’t have the budget), I just started hosting free talks. It was always about something startup-related, and often I didn’t even lead them, rather I got someone else a lot smarter than me to do it. I just promoted it. For instance, Jason Mendelson on “20 ways to f*ck up your company”, or Paul Berberian on the hilarious Zenie bottle story, or Matt Blumberg on how to be a CEO. It was usually an hour long, and I always ended it with “and Techstars applications are open until X – if you have any questions, I’m here and would love to talk to you about it”. The key was the talks were GOOD. They were educational, from people who knew what they were talking about.  And when event attendees saw this small show of value, they could imagine what a whole accelerator program might be like. I often spent sixty minutes or more after the talk answering questions for people interested in the program. And so the flywheel of marketing began to turn. That piece of guidance was a huge driver of the early success of Techstars.

Fast forward a bunch of years, and the same thing happened with Digital Ocean. They were in their infancy, were a cloud hosting provider up against complex behemoths like Amazon, but had some very lofty growth goals. Digital Ocean was proud of how few clicks it took to set up a web server on their hosting platform relative to Amazon which could take hours to figure out. Taking a page out of “add value first” – they followed some sage advice from Jason Seats; rather than buying ad space, they created a bunch of how-to articles including a lesson in how to set up an Amazon web server without errors, literally helping people be successful on their competitor’s platform.  However at the very end of the post, they said “…and if you don’t want to do this work, check out Digital Ocean”. What I loved about this approach was their main focus wasn’t promoting Digital Ocean (although they hoped that they would get customers out of it). Their main focus was making someone else’s life easier.  They eventually IPO’ed, the roots of adding value embedded deep within the fast-growing company.

Companies spend billions of dollars a year trying to get our attention, such as all the ads we are subject to, or that sponsor who paid good money for brand recognition and 5 minutes on a stage. We are so overrun with this noise, that we tune it out – and the response of the marketing departments is to spend MORE money, say it louder, say it more often, creating more noise and making us filter it out even more. It’s a vicious cycle of absence of substance. 

If you want to get someone’s attention, try adding value first. The trick is that value is in the eye of the buyer, not the seller, so you really need to think about what your audience values. Taking out advertisements to tell me how awesome your CRM is doesn’t add value to me, even if I need a CRM, because every CRM is doing the same thing, so it’s just more noise. But taking out an ad to market a free class or video on how your CRM syncs bidirectionally and seamlessly with no code to that spreadsheet my intern uses, and then giving me a month free trial for taking the class? Love it.

Consider setting up a challenge in your company for your marketing team – ‘You aren’t allowed to market. You are only allowed to teach – even if it’s teaching about how to use a competitor’s product’.  How about co-writing a blog post with an investor about some challenge your business is facing, and letting that investor publish it on their website? The ideas are endless, you just need to think creatively.

Adding value takes thinking outside the box, I dare say it’s applicable in everything you do, and when you get it right, people will trust you more. Your customer base will be more tightly vetted, leading to happier customers with longer LTV. Your investor will be more likely to fight for you and bridge your next round when things aren’t going as planned (and let’s be honest, they RARELY go as planned). 

Challenge yourself to find a way to add value in every interaction. You’ll end up with a tidal wave of support that lifts you higher and propels you farther than you could ever imagine.

Nailing your vision is only step 1

Nicole Glaros2 Comments

I’ve recently worked with 2 different companies who are struggling. In trying to help diagnose the issue, I talked to a handful of people (board, leadership team, employees, etc), and when asked “in your own words, tell me what the vision of the company is” – I heard surprisingly different answers. 

We all know how important vision is – in fact, we know it so well that we dismiss it. “Yeah yeah yeah, it’s table stakes, we did that already at last year’s offsite… don’t tell me about how important vision is.”

Yet vision itself is important only to the extent that:

  1. You have one (obviously)
  2. Others know specifically what it is (communicated); 
  3. It can’t be interpreted any other way (clarity), and 
  4. That people on the team are 100% bought into it, emotionally (alignment).

This is where I see a lot of companies go wrong – you need all 4. Ironclad.  Founders invest in the vision, but not in the other 3 steps, and eventually, things go sideways for them.  Let’s break it down.

You have a vision

I’m not going to spend a lot of time here because there have been entire books written about the subject. Just know that it’s not the same thing as your marketing tagline. It’s a rallying cry, it’s your ‘why’, it’s the reason your employees want to work for you and the reason you get up in the morning. Nietzsche famously said, “He who has a why to live can bear almost any how”. By the way, profits are not a good rallying cry.  Numbers, generally, are not. Also know that your vision is not your ‘how’, how specifically you’re going to accomplish your why. Your “how” is very necessary as well, and needs the following elements too, but that’s for another blog post.  

Now if you don’t have a vision yet, it’s okay, you’re exploring, discovering. Try not to succumb to the temptation to raise capital at this stage, it’s fundamentally misaligned with discovery (and that is yet again fodder for another blog post).

You’ve communicated it with others

Everyone, and I mean everyone, in the company should know what the vision of the company is. Nearly verbatim. The board, the leadership team, the new hires and interns. People should be able to state it, within a couple of word difference, upon demand. It should be easy to say and easy to memorize, and you should repeat it ALL THE TIME. An exercise once a year doesn’t cut it. Consider every offsite, every board meeting, every all hands – there is a lot of places to repeat your rallying cry to ensure it’s etched in stone.

This is very easy to test by the way, but it can’t be done in a way that gives people the chance to look up the answer, or if they get the wrong answer, they’re in trouble. If you’re in-person, get an advisor or friend of the company to walk around and ask people what the vision is. Have this person keep track of how many seem on point vs off track. It doesn’t need to be super scientific.  Or if you’re on Zoom, there’s a quiz feature that allows for short answers – the goal is to not give people enough time to go look it up, and done in a way that people don’t feel threatened.  Zoom is nice because you can see how off people are. Remember, deviations aren’t their fault, they are yours. Re-train.

Clarity: It can’t be interpreted any other way.

You would be shocked at how different interpretations can be, and when people think it means something different, then people aren’t working towards the same goal. It’s almost the same thing as not having a vision in the first place.  

Again, the test here is pretty easy, just ask!  At your next allhands, ask everyone to come up with various interpretations to the vision. Give an award for the craziest interpretation – make the object of the game to INVENT interpretations, so people don’t feel threatened. Then edit the vision statement as necessary to improve clarity.

Alignment: people are emotionally bought in

This one is the silent killer. Do people really buy in to your vision? How do you know? Just because they’re not debating or not pushing back, doesn’t mean they’re bought in. Whenever people aren’t debating, I’ve found it means one of three things:

  1. They agree. IMHO I find this case the least likely of the options, yet CEOs think it’s the most common. Beware.
  2. People disagree but they aren’t pushing back and helping you refine it because they don’t feel safe to disagree with the boss.  This causes much bigger issues in the company beyond vision.
  3. They disagree, they’ve told you so, they don’t think you’ve listened, or don’t care, they think you’re wrong and aren’t ‘disagreeing and committing’. They are going to do it their own way, your way be damned. Or they’re going to do it your way, but do it half-assed, so that mistakes abound.

This one is much harder to test becaues people won’t readily admit to it, and once you’re far down the road on issue 2 or 3, it’s hard to repair. The best way to avoid this fate is to start early, ask often, remember people’s concerns so that when you’re wrong and they’re right, YOU say so and not them, and ask people to disagree and commit. A good tactic for this is the Fist of Five, where everyone, simultaneously, votes with their fingers a score between 1-5, where 1 is “hell no, this is a freaking mistake”, 3 is “maybe, I need more info”, and 5 is “hell yeah, let’s do this”. 

Without communication, clarity, or alignment, your vision is merely hallucination (thanks to Gino Wickman for that little nugget). People always seem to focus on the vision, that’s where they put their greatest attention. But remember you aren’t done once the vision is decided. It then needs to be communicated effectively, without room for interpretation, and people need to be bought in. From there, THEN you focus on how to execute the vision. Otherwise the time you spent on vision is wasted and it will have little to do with outcome of the company.

If the company is struggling generally and you’re having a hard time putting your finger on why, run through the above exercises to rule out murky vision and alignment as the reason why.

Now go thee and conquer!

Bigger isn’t always better, better is better

Nicole Glaros3 Comments

There is a long-running belief that things grow or die. In startups and in business, growth tends to mean more topline revenue.

But growth doesn’t have to mean more topline revenue. Growth can also mean improvement, better; better product, better systems, better processes. Here’s the thing (I always have a thing), better almost always leads to bigger, naturally.

The challenge with focusing exclusively on topline revenue when you want to grow is that problems nearly always scale faster than solutions.  When you throw dollars into marketing and sales, without a healthy, underlying business, the top line will grow, giving you false positive feedback, which leads to you to keep spending. However, problems are being created, and are scaling faster than the revenue, and eventually those challenges will consume the company leading to its ultimate demise. For instance, you can’t see that the CAC to LTV ratio no longer works – or maybe it never worked and you figured that by spending more in different niches, it would eventually work. Or maybe you don’t even know what the unit economics actually are, and you’re scaling a business that fundamentally doesn’t work. Or you can’t see that there’s disagreement on the direction of the company at the leadership team level. Or you can’t see that while growth is happening, customer returns/dissatisfaction and churn are happening at a faster rate than before. Or your team spends more time firefighting than driving results, creating incredible inefficiencies and destroying the bottom line (not to mention the employee turnover).

But if you focus on better, the company’s topline revenue often will grow naturally without any additional sales and marketing effort, and often with the same, dare I even say lower, costs – making the business itself healthier in all dimensions.

For instance, a focus on a ‘better user experience’ will ultimately result in:

  • Fewer customer support calls
  • Fewer bugs
  • Happier customers
  • Fewer refunds
  • Higher lifetime value, more renewals
  • Lower churn
  • Higher referral rates, increased virality coefficient or network effects
  • Happier employees
  • All of these items equal less cost, or more revenue, or both.

The better approach indeed takes more time to flow through your company compared to the let’s just throw more marketing/sales dollars at it approach – but it absolutely leads to a healthier, more successful company. And when it’s healthier, it will ultimately lead to bigger top-line revenue.

Now, I’m not saying you shouldn’t spend more on marketing/sales when you want to grow, but I am saying that you should take a hard, long, honest look at the business before you do so. 

Before you decide to scale the business:

Understand the unit economics and the levers of the business first. What are your unit economics? $1 spent in sales/marketing = how much in revenue? If you don’t yet know your unit economics or the levers that drive the business, you are not ready for growth. You absolutely need to know these metrics before stepping on the gas, otherwise, you’re just burning cash and praying for a miracle. Not sure how to go about this? Check out the book Levers by my dear friend Amos Schwartzfarb for a crash course.

Look for areas in the business to improve.  Here are common ones:

  • Product market fit – are you really in the best market for your offering?
  • Removing bugs (everyone’s least favorite – but reduces customer support costs and improves customer satisfaction)
  • Improving UX, steps, clicks, intuitive workflows, etc
  • Become obsessed with reducing the number of customer support calls because customers just get it, and it just works.
  • Become obsessed with how much customers love your product. What features can you remove (not add), or what niche can you focus on, to improve the love.
  • Removing steps in any process you have internally – this will reduce employee time spent on ‘tasks’
  • Removing policies – policy is never a good substitute for holding people accountable for good judgment, and it slows everyone down.
  • Identify redundancies in the business and remove them.
  • Look for gaps in the business “it’s not my job” and fill them.
  • Push reversible and inconsequential decisions down in the business as low as you can get them 
  • Improve alignment – is everyone incentivized similarly, or by the right things? Make it so.
  • Simplify – what areas can you simplify? Org structure, processes, policies, product.

Monitor the unit economics and key levers as you work on areas to improve, you should see movement! Maybe you started at a $1 marketing/sales spend = $3 revenue ($1:$3), and through your efforts it grew to $1:$4. Hell yeah! Be a little patient though, it can take 6-12 months to flow through the system.

Once you decide to increase sales and marketing spend, keep an eye on those levers and metrics – when you see the ratios start to head south, hold or reduce spending, and investigate. Don’t just keep throwing money at it.

The one exception to this is when your company is very early stage, and you have little to no revenue. But then your focus isn’t on ‘growth’, but rather finding out if you have product market fit (PMF). Don’t confuse the two. A doubling of your customer base or revenue doesn’t necessarily mean PMF. The best measure of PMF that I’ve seen is called the Sean Ellis test, whereby >40% of your customers would be ‘very disappointed’ if they couldn’t use the product anymore. Now, you need a customer base large enough to have statistical significance, and in most mathematical circles, that’s >30, however, I recognize if your customer base is large enterprises, that might be challenging.  But I digress.  If you’re still in PMF mode, do not, I repeat, do not focus on growth. Focus on PMF. Don’t focus on growth until you’re sure you have PMF.

However, there is a play that says “grow at all costs”, and on extraordinarily rare examples, this play works because you can have market effects. Grab as much of the market as possible, which will kill the competition, and then focus on quality later. But for this play to work, you have to be in a winner-take-most market, you have to be extraordinarily well funded, with low-to-reasonable valuations, and very understanding and aggressive investors who commonly invest in the next rounds even if the fundamentals of the business aren’t yet healthy, in a highly stable or growing market cycle. Given all of that is out of your control, you literally cede control of your future and company to fate. Your success lies in the hands of luck, not skill. If it were me, I’d want to stack the odds in my favor by building a healthy business before focusing on growth.

This year, as you’re working on your budgets and strategic plans, consider a focus on quality, a focus on better. Then enjoy bigger happen naturally, with lower costs and headaches, and more pride in what you’ve built.

Play to win, don’t play to not lose

Nicole Glaros6 Comments

I recently gave a talk to a room full of founder/CEOs about how to leverage your board of directors by shifting from a reporting board to a collaborative board.  It can be tricky, but for those who do it, the company and the founder can grow wings. Part of the shift involves trusting your board and bringing them into your confidence, being vulnerable with them, and asking for their help and input when things aren’t working.  This can be scary for most CEOs because the board usually has the power to remove him/her. However, if you have the right board members, and if you create the right dynamic at the board level, this usually won’t be the outcome.

One founder in the room raised his hand to challenge me. He said, and I’m paraphrasing here, “That’s a lot of ifs and usuallys. Why would I take that risk? If my board can fire me, why would I risk being fired and losing my company by admitting weakness and vulnerability?”

I love this founder for asking that question – it’s at the heart of why most CEO’s don’t go to their board with challenges.

Here’s the thing: There’s a difference between playing to win, and playing to not lose. 

Let me tell you a quick side story. I played volleyball in high school and club ball in college. I’m short, so was never going to be really good, but I loved it. My freshman-year dorm was across the street from a frat house with a sand court in the front yard, and I was dumb enough to ask to play with the guys who were much taller and more skilled than I was.  They were nice enough to let me participate, and for a whole year I spent every day after school and all my weekends there. Eventually, I got good enough to hold my own, and we competed in a few sand tournaments. I never won, but placed decently, and even taught the volleyball class at the University for a while.  

Fast forward 20 years, I started a couple of companies, had a couple of kids, moved a couple of times, and made 100+ investments, raised a couple of funds, traveled an inhumane amount, had a ludicrious number of direct reports, helped grow Techstars… basically, I had zero free time to do things I loved like play volleyball.

So recently, I decided to pick it up again. I found myself on a co-ed, indoor sand team. I was pretty nervous to start, but hey, I’m decent at this sport, so I figured once I got my legs under me again, I would be okay. Well let me tell you – I was bad, so embarrassingly bad. I shanked every pass. Put every attack in the net. Dove and missed every ball. Lost every overhand serve. It was so bad that one teammate asked me to serve underhand, a big hit to my already fragile ego.  It’s been a long time since I felt that humiliated. We lost every game that season and were relegated to the lower league, largely because of me.

Astonishingly I was invited to play the next season (I’m 100% sure it was because they couldn’t find anyone else), so I swallowed my pride, said yes, and started practicing, figuring my ego needed to practice sucking in public. Luckily I got better and better. I wasn’t anywhere near as good as I was 20 years ago, but at least I wasn’t an embarrassment anymore. Yet I continued to serve underhand – because I was so afraid of losing the serve. A killer overhand serve will earn you points, but a bad serve will earn the other team points. You can win whole games on a killer serve alone. When I practiced, my overhand serves were killer. They were strong and hard to return and my team kept asking me why I wasn’t serving overhand in the games, but the truth was I was afraid to choke. I didn’t trust myself anymore and I didn’t want to cost us the game. I was playing to not lose, I was not playing to win. Despite my conservatism, our team placed #1 in that division and got promoted back up to the higher league, but, I didn’t get invited back to the next season because I didn’t help win games. I just helped not lose them. And quite frankly, I don’t blame them; they wanted to win.

This founder’s question is like my underhand serve. It’s playing to not lose. And when you’re in the high-stakes game of entrepreneurship, especially if you’ve taken venture capital, there are only 2 outcomes, winning, and losing. So if you’re playing to not lose, you will likely, eventually, lose. 

Here are common behaviors I see founders take that show they are playing to not lose:

  • Not being honest with the board
  • Stacking the board with friends rather than skills/knowledge/wisdom/networks/courage/honesty
  • Not asking for help
  • Trying to be good at all things
  • Not having a difficult conversation with a co-founder, leadership team member, investor, yourself
  • Not asking for feedback
  • Dismissing other people’s feedback
  • Needing to win disagreements
  • Not hiring people smarter/better than they are
  • Hiring up, and scaling up before true product / market fit
  • Trying to raise more capital because you hired/scaled faster than you should have before you have product market fit, and you’re now out of runway
  • Trying to keep the business alive when there’s clearly no real business, and burning through all the investor capital without returning any of it
  • Not making a major decision
  • Micromanaging, not trusting your team
  • Using policy as an excuse or crutch for not developing judgment

There are infinite ways that playing not to lose manifests but at its core is fear; fear of failure, fear of loss. The trouble with this behavior is that it almost always manifests that which you are exactly trying to avoid. For instance, not being honest with the board will eventually lead the board to not trust you, which will either cause them to not vote with you or they will try to remove you as the CEO. It just takes longer, but in the interim, you’ve burned all the bridges and not gotten the help, trust, and support you needed to turn the issue around.

Don’t mistake playing to win as ruthless, win-at-all-costs actions; that simply isn’t true either. You might win a battle, but you will eventually lose the war. Playing to win does mean taking risks, but it means taking calculated risks intentionally, collaboratively, and intelligently. In the land of startups, a win-win-win outcome is possible because together you can create more value than you othewise could apart.

Here are excellent playing-to-win behaviors:

  • Recognizing your weaknesses and staffing for them
  • Asking for help, asking for feedback
  • Admitting a mistake, asking for forgiveness
  • Build and manage a board of directors that can be as influential as your leadership team
  • Make a hard decision, even if unpopular
  • Hold people accountable, especially yourself
  • Taking a big swing, that’s calculated, intentional, aligning, and collaborative, with tailwinds
  • Having a scary conversation with someone
  • Conserving every f’ing penny until you have product market fit
  • Keeping your day job/not raising money until you have product/market fit
  • Shutting the company down and returning capital to investors when you can’t see how you’re going to make it work
  • Saying NO to distractions
  • Being generous with equity with the *right* co-founders, employees, investors
  • When people disagree with you, get curious, not defensive
  • Investing in your own professional development
  • Identifying the one thing your business can be best in the world at, and going hard at it. Don’t make marginally improved products/services.
  • Recognizing when you aren’t best suited for your role in the company anymore

Of course, all of this is situationally specific, and the true answer to any question is “It depends” – but I ask you – are you playing to win? Or are you playing to not lose? Are you serving underhand? Or overhand? What can you do or stop doing to shift to a winning orientation? I encourage you to ask that question, not only of yourself, but together with your team and your board.  “What could WE do, or stop doing, to help us shift from playing to not lose, to playing to win”. What a powerful way to reorient and kick off a new year.

How to make better decisions

Nicole GlarosLeave a comment

Early in my career, I learned how important it was to make great decisions. When you’re investing, your performance as an investor is directly tied to the decisions you make, but with early-stage investing, you don’t find out if you’re right or not for a decade or longer. Then when I started to train and manage many of the Managing Directors at Techstars, learning how to make better decisions became a scalable challenge and opportunity, because now we had dozens of people making investment decisions. How to help them all improve their decision-making abilities tied directly to the returns we generated and the bottom line of the company.

I’ve been meaning to write a series on how to make better decisions, but haven’t seemed to get around to it (this is a good segue to time management and prioritization, but that’s for another post). Luckily my friend Matt Blumberg, CEO of Bolster created a 6-minute podcast on the topic. So while this doesn’t cover all the topics in how to make better decisions, it is a great summary.

Check it out here!

Navigating Your Startup Board of Directors: The Meeting – Part 4 of 4

Nicole Glaros1 Comment

This is the final part in a series on getting the most out of your startup board of directors. If you haven’t already, please read Part 1: The Framework, Part 2: The People, and Part 3: The Board Package.

Special shoutout to my friend Ari Newman, Managing Partner at Massive who served as an editor, contributor, and sounding board for this series.

You’ve come so far, my friend!  You’ve got yourself in the right headspace about how your board is your not-so-secret weapon, you have the right people on your board, you’ve established a highly functional, productive, and trusting relationship with them, plus you’ve created a killer board package.  Now it’s time for… dum dum dummmmm, the meeting. In all honesty, once you’ve done the above things well, the meeting is the easy part.

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Navigating Your Startup Board of Directors: The Documents – Part 3 of 4

Nicole GlarosLeave a comment

This is part 3 of a series around navigating your startup’s board of directors. It focuses on the board package, what documents and sections to include and how to organize it. If you haven’t yet done so, please read Part 1 – The Framework and Part 2 – The People.

Special shoutout to my friend Ari Newman, Managing Partner at Massive who served as an editor, contributor, and sounding board for this series.

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