Dec 9 2021

Top 3 Mistakes Early Stage Founders Make

I just did a podcast recording the other day for someone who asked me the biggest mistakes founders make and what to do about them. I divided my response into “early stage” and “later stage” founders. Here’s a summary of what I said about early stage founders.

  1. They cling to a “good enough person” or someone who is a good performer but a weak cultural fit because they either feel beholden to that person for their output, or worse, they’re actually afraid of losing them because they’ll miss a milestone or maybe trigger some other departure.

    The “what to do” of course is to have courage and make the change! I wrote an essay years ago in Brad Feld and David Cohen’s book, Do More Faster, entitled Hire slowly, Fire quickly, in which I compared a poor cultural fit to a cancer that can infect the whole body of your company. A “good enough” person obviously isn’t quite that toxic, but someone like that can still prevent you from achieving your potential. In either case, the faster you realize what’s going on and make a move, the better off you are.
  2. They get the balance wrong between “leading with vision” and “listening to customers”. Both are important for founders, but you can’t do too much of either. It’s really easy to get led to a too-narrow Product/Market Fit definition that has you building something awesome that only a dozen customers will be excited about That said, founders also have to listen if enough potential customers people say no. Your vision could just be too far ahead of the market.

    You have to get around this by constantly checking your enthusiasm with a mix of cold hard logic. Lots of market traction is great — but is all that traction coming from the same type of customer? Have you run your idea or wireframes by different segments, different buyers, different sizes of company (if B2B) or lots of different demographics (if B2C)? Are all of them equally enthusiastic and willing to buy? A complete lack of market traction when you’re sure your vision right is equally vexing. If literally everyone is saying “no” or worse, some polite but noncommittal version of yes, are you working to shape the vision, or at least shape how you articulate it? Sometimes your vision might be right, but your messaging might be off. Try different ones on for size.
  3. They focus on fundraising and valuation over business fundamentals. Especially in this day and age, it’s really easy to get caught up in the “more money” hamster wheel. Raise, raise, raise. Finish one round, immediately start working on the next.

    In the end, business fundamentals matter — no fundamentals, no business (e.g., no next round). More than that, spend more time caring about your customers and learning and telling stories about how you made their lives better with your product or service. That’s more important to your next fundraise than just blowing through one round of money to get to the next.

Next week: the later stage founder answer (link won’t be live until 12/16/2021).

Dec 2 2021

When it is Time to Hire Your First Chief Financial Officer

(This is the second post in the series…the first one on How to Engage with Your CFO is here.)

What comes before a full-fledged CFO?  Lots of startups have nothing more than an outsourced bookkeeper or one junior staff accountant.  Sometimes a founder or a founder’s spouse even steps in on this front.  As startups scale, they are likely to hire a more senior accountant, maybe an AR/AP/Collections staff member, or even a Controller or VP Finance.

Depending on the complexity of your business you might be able to hold off on hiring a full-time CFO, but if you have any of these signs then it’s time to start thinking about bringing someone on board. One sign is intuitive, and it’s just the feeling that you’re concerned about cash. Maybe you wake up in the middle of the night and that’s what’s on your mind—not just that you’re running out of cash, but that you aren’t clear on how much cash you have and how fast you’re spending it. Is it concerning that you’re tight when it comes to payroll? Are you getting calls from vendors about late payments? Are you way under market in compensation and trying to overcome that by offering equity or “perks” to attract top talent? These are all telltale signs that your financial situation may be under duress, and a full-time CFO can be a solution.

 Another telltale sign that you might need a CFO is more tangible: Are you spending too much of your own time managing fundraising, debt, investors, and cap table questions and issues? If you are in the weeds with the financial reporting, either fixing what’s there or creating a lot of things from a blank slate, then there’s an obvious problem, and solution.

 Another sign that you need to hire a full-time CFO comes in the form of things you can’t answer. If your board asks you about some small-to-mid-level analysis or metric like CAC, customer profitability, margins, or ROI, and you don’t have a great answer that’s a signal that your finances are out of control. And if you can’t figure out how to get to an answer, that’s even worse.

 Of course, you don’t have to wait until these telltale signs emerge before hiring a full-time CFO—it’s also possible to have a discussion with your current finance person and figure out together what their career path could be, and what their aspirations are. If your finance person aspires to be CFO but doesn’t have the skills (yet) consider bringing on a fractional CFO. A fractional CFO may be the way to go if your business model is simple…some combination of a limited number of complex accounting issues, a limited number of customers or invoices or transactions, and an insignificant difference between the income statement and the cash flow statement.  If what you need is someone to oversee a gradually growing team, a slow-paced implementation of higher-order systems, basic financial analysis or modeling, or the occasional fundraising event, a fractional CFO may get the job done, for several years. A fractional CFO can also mentor your current finance person in the realities of the CFO role, and they can help you find a qualified CFO who will be a good fit for your company.

While there is no fast and easy answer about when to hire your first CFO, there are some telltale signs that point to that direction and if it’s not in your budget, consider a fractional CFO to help get things under control before you really do run out of cash.

(Posted on the Bolster Blog here)

Nov 24 2021

Offsites in the age of COVID

I attended two offsites in the last two weeks – both great in terms of seeing people in person.  Interesting how differently they handled COVID protocols, although they were different groups with different vibes.

One was a CEO conference for one of my VC’s portfolios.  There was a huge emphasis in all the pre-conference comms about COVID.  And lots of testing.  We all got mailed a very sophisticated in-house PCR test ahead of time to take and photograph/upload, complete with chemical reagents and some kind of centrifuge.  Then those of us who flew in for the event had to do an on-site rapid test before entering the opening reception and even had a side room to sit in for 15 minutes while we were waiting for the rest results.  Once in the room, everyone was super awkward at the beginning.  Should I wear a mask?  Do I shake hands?  Hug?  Wave?  Bump elbows?  But once we got into the flow of the meeting, people were more relaxed and interactive…even some close talking.

The other was my company, Bolster – our first ever “all hands” meeting in person (we started the company just 18 months ago and have people in multiple locations).  The COVID topic was almost nonexistent.  We only have 25 people, and everyone is vaccinated, no one is immuno-compromised, and the couple of people with young and unvaccinated children are very much not on lockdown (that could be more regional – I see that more in NY than in CA).  We simply asked people to get tested before they come on the honor system and then told people when we got there that people should do whatever they were comfortable doing in terms of masks and contact, no judgment.  There was no awkwardness that I could tell at all.

In terms of the meetings themselves, both were great – it was fantastic to be live with other humans!  While there is a lot to be said for the efficiency of 15 and 30 minute meetings on Zoom, that pattern of work can’t be 100% of your year.  It doesn’t allow for serendipitous hallway interactions or highly effective design collaboration like whiteboards and post-its do.

What neither group nailed was blending people actually at the offsite with a few people who didn’t want to, or couldn’t, attend in person.  That’s got to become the norm for offsites going forward, for sure.  Videoconference software or hardware/software combinations need to get better at supporting the hybrid environment for sure, but so do meeting facilitators.

All in, while I’m looking forward to traveling less in the future, there’s much to be said for meeting in person from time to time and figuring out how to optimize that time.

Oct 28 2021

I’m Having a Blast at Bolster — Here’s Why

Someone asked me the other day how things are going at Bolster, the new company I started along with a bunch of long-time colleagues from Return Path last year. My visceral answer was “I’m having a blast!”  I thought about it more after and came up with five reasons why. 

First, I am working with a hand-picked group of people. My co-founders, I’ve worked with for an average of 15 years – we know and trust each other tremendously. And for the most part, the same is true about our cap table. Almost everyone else at the company is also someone multiple of us have known or worked with for years. That may not last forever, but it makes things so much easier and almost friction-free out of the gate here. 

Second, this is the “second lap around the track” for a few of us on the founding team in terms of starting something from scratch, and even those at the company who haven’t done a raw startup before are super experienced professionals and many have worked in and around early stage businesses a lot. All this combines to cut down our error rate, reduce anxiety, and speed up the pace of work. More friction-free or at least low-friction work.

Third, after a 20-year run at Return Path, it’s great to start with a clean slate. No mountains of tech debt and legacy code bases. No installed base of customers with contracts or pricing we no longer like or offer. No institutional debt like a messy cap table, legacy people issues, leases for offices we don’t want or need any more.  This also points to low friction as part of what’s going on…and while that’s a theme, the next two areas are different. 

The fourth reason I’m having a blast at Bolster is that I love — and really live in — the problem space we are working in.  When we started Return Path, I was deeply familiar with email marketing and the challenges faced by our client set and had a good vision for the early product.  But as the years went on, the product got geekier and nicher — and even when it wasn’t, I was never a USER of the product since I’m not an email marketer.  In fact, at our peak of 500 people, the company employed one email marketer and therefore had one user of our own product.  At Bolster, we have three user personas — Member, Client, and Partner.  And I’m all three of them.  I’m constantly in the product, multiple times a day.  I’m deeply familiar with all angles of the executive search and board building process.  It’s MUCH better to be this close to the product, and the same is true for many of our team members.

Finally, the thing I was really worried about with starting another company from scratch — moving from a leadership role into an individual contributor role — has been nothing short of fantastic.  I love working with clients.  I love talking to members.  I love advising and coaching CEOs. I love being a pretend product manager.  I love writing marketing copy.  It’s just great to be on the front lines. (I still love working on strategy and leading the board and engaging with people internally — but those are things that never stopped being part of my day to day.)

I was trying to think if there’s some priority to this list. Almost all of these items are or can be made to be true in your second+ startup. But while four of the five can theoretically be true in your first startup as well, I don’t think it’s quite the same. So I’d have to weight “second lap around the track” a bit higher and also note that during your second lap around the track, hand-picking your team and cap table, appreciating a clean slate, and appreciating individual contributor work are that much easier and things you can appreciate a lot more as a repeat entrepreneur.

Oct 21 2021

How to Engage with Your CFO

It’s fairly rare in a startup or scaleup that you, as a CEO or CXO (Chief [fill in the function] Officer) of any kind, will have significant one-on-one time with other members of the executive suite; instead, you’re most likely to spend time with the team in executive meetings, at offsites, or during all-company events. So, when you do get that one-on-one time it’s important to make sure that it’s not only productive, but that it builds a stronger relationship between you and the other person.

As a CEO I learned that the best way to help people grow and develop, and to further develop a better understanding of each other, is to engage with them in a mix of work and non-work settings.  By that I mean, working together on some aspect of their part of the business. Since each role and each person performing that role are different, there aren’t any hard and fast rules, but I thought I would create a series of posts that provide some ideas on things I’ve done to develop a better relationship, better team, and better company for each CXO in a company. 

I also have a whole series of posts related to each function on the executive team — CFO, CMO, CTO, etc.  So each post is part of two series.  This is the inaugural for both, and it’s quite fitting as Q4 is, for most companies, budgeting and planning season.  So today’s topic is How I engage with the CFO.

When I get the chance to spend time with my CFO I’ve found that we both get the most value working on several “problems” together. For example, we do Mental Math together where we look at key metrics and test them, improve them, or decide to scrap them. We are always attuned to key metrics and from time to time, we project them forward in our minds. What will happen to a key metric if our business scales 10-fold or if it declines 10-fold, for example. 

We are constantly checking to see that our financial and operating results mesh with our mental math.  When looking at our cash balance, we’ll look back at the last financial statement’s cash number and mentally work our way to the current statement: operating profits or losses, big swings in AR or AP, CapEx, and other “below the line” items. Do they add up?  Can we explain what we’re seeing in plain English to other leaders or directors?  The same thing applies to operating metrics — the size of our database, our headcount, our sales commission rate, and so on.

I’ve found that by working on the mental math that we actually come to understand the dynamics of the business far better than merely looking at the numbers or comparing the numbers. The mental math approach forces both you and the CFO to engage with the results, question them, and anticipate how slight changes can impact the company going forward. And once you get to that point, you have the ability to creatively think about how you want to go forward.  Here’s a simple example from the early days of Return Path.  One day, my long-time business partner and CFO Jack and I were doing mental math around how many clients each of our Customer Success team members was handling.  We had an instinct that it wasn’t enough — and we did a quick “how many of those reps would we need if we were doing $100mm in revenue” check and blanched at the number we came up with.  That led to a major series of investments in automation and support systems for our CS team.

Another way that the CFO and I work together is in a game called “spotting the number that seems off.” In any spreadsheet or financial analysis there is bound to be something that doesn’t seem quite right and for some uncanny reason, I am really good at finding the off number. I’m sure this has driven CFOs crazy over my career, but for whatever reason I have some kind of weird knack for looking at a wall of numbers and finding the one that’s wrong.  It’s some combination of instincts about the business, math skills, and looking at numbers with fresh eyes. It’s not an indictment on the CFO’s results and it’s not a “gotcha” moment but it’s part of the partnership I have with my CFO that improves the quality of our work and quantitative reasoning. My hunch is that looking at something with fresh eyes, as opposed to being the person who produces the numbers in the first place, makes it easier to spot something that’s not quite right. Kind of like an editor working with you on an article or book—they always seem to pick up and point out something that you didn’t see even though you spent hours creating it and hours more reading and re-reading something.

A third way to work with the CFO is to create stories with numbers. The best CFOs are the ones who are also good communicators — but that only partly means they are good at public speaking.  Being able to tell a story with numbers and visuals is an incredibly important skill that not all CFOs possess.  Whether the communication piece is an email to leaders, a slide at an all-hands meeting, or a Board call, partnering with a CFO on identifying the top three points to be made and coming up with the relevant set of data to back the number up — and then making sure the visual display of that information is also easy to read and intellectually honest, can be the difference between helping others make good decisions or bad ones.

Of course, a CFO could create stories on their own but like much of storytelling (like screenwriters for movies, plays, or sitcoms, for example), the creative storytelling usually happens with a team. In presenting financial data to others so that it makes an impact, so that it motivates them to take an action or change a behavior, a team approach is best and the CEO-CFO team can be much more effective than either one of them alone.

You won’t have a lot of time to spend 1:1 with any given CXO on your team, including the CFO, but you can make the time you spend together work to your favor in developing a stronger relationship between you and the CFO, and help you build a stronger company that can scale quickly. Without a deep understanding and strong relationship with others on your leadership team, your decision-making, speed, and risk-taking can suffer. Make sure every minute you spend with the CFO is productive. That’s why working on things together like mental math, spotting the off number, and storytelling, can be powerful ways to help you build a better company. 

(Also posted to the Bolster Blog).

Oct 14 2021

Momentum and Confidence: Everything Matters

As I stared at a dugout of dispirited 14 year old boys Saturday afternoon in our tournament championship game, I found myself talking to my fellow coach Mitch about a book I’d read a few years ago (turns out 14) called Confidence: How Winning Streaks and Losing Streaks Begin and End, written by HBS professor Rosabeth Moss Kantor. While that original blog post is pretty specific to something that was going on at that point in time in my prior company, the thinking in the book about momentum and the role it plays in our psychology, about sports, about business, and about life in general, is timeless.

Watching this team of teens go through ups and downs within an hour was incredibly stark and clear. In the first inning, we made three errors (just jitters from being in the championship…the Bulldogs are better than that!). Those opened the door for our opponent to post a few runs and take a quick lead. It was as if the wind had been taken out of our sails, as if all 11 kids just took a punch to the gut. They were shocked and pretty listless in the dugout, and nothing the coaches could do or say shook them out of it. They just *knew* they were going to lose, so why try? Their confidence was gone. It wasn’t until we staged our own big rally, later in the game, where all of a sudden, one, then two, then three base hits and the kids were going bananas, up at the fence of the dugout and screaming, cheering each other on and feeling all of a sudden like we could win the game.

The swing in momentum took about 5 minutes in each direction. And all that was involved was a couple quick negative/positive indicators/actions.

The bottom line is that we still lost the game 10-5. But the energy that came from a couple positive developments that stopped a downward spiral and started an upward one was palpable and instructive. As one of my other fellow coaches Jay said to the boys after the game, “Boys, the lesson from today is that Everything Matters. We lost 10-5, but when we were only down by 5 runs with the bases loaded, how much did we regret those couple of errors in the first inning? Without those, we would have been down by 2 runs with victory in reach.”

It’s the same in startups.

When you run a startup, you regularly take three punches to the gut in a row — a client cancels on you, you have a web site outage, an employee quits — and all of a sudden, you view the world through a dark lens of, as my long-time friend and Board member Scott Weiss used to say, WFIO, short for We’re F#%ked, It’s Over (pronounced whiff-ee-oh).

And then, the opposite happens, and it’s like the heavens part and the angels start singing a hallelujah chorus. You win a big new deal. You get unexpected positive press or a key blogger or tweet creates massive buzz for you. Your CFO pings you with the news that revenue is surprisingly high this month. WFIO is suddenly replaced with what I’ll call WGTWIA — We’re Going to Win It All (let’s pronounce it wig-twee-uh).

And what’s the difference? Probably nothing big. Probably a couple small things that just happened to break in the right or wrong direction at the right time. That call or email you decided not to return for a couple days until it was too late. That presentation you could have spent an extra 45 minutes perfecting instead of half-assing. That extra run through a new module of code you wrote to make sure it’s fully debugged. Just like a few silly errors in 14-year old baseball because you had the jitters early in a big game.

Everything Matters. In sports, in business, in life. Anything you think is a “throw away” can turn out in retrospect to have made the difference between winning and losing, between success and failure.

Sep 2 2021

Why the Startup Sales Function Starts With Whiteboards

(This post was inspired by Startup CXO and was originally published by Techstars on The Line.)

In most startups, one of the founders is the first salesperson — often out of necessity as much as passion. But as startups scale they add sales reps or maybe some form of a Sales Manager once there are more than a couple of reps. But how do you know when to bring on a senior sales leader? Too soon and you have a very expensive employee, too late and your sales reps are creating their own processes and approaches. As a CEO there are several telltale signs that you need to hire a CRO, for example:

  • You wake up in the middle of the night concerned about HOW you’re going to make this quarter’s number. You have no clue about what the levers are, or what the pipeline/forecast details are, to get there.
  • You are spending too much of your own time managing individual deals and pricing, or teaching individual reps how to get jobs done.
  • Your Board asks you if you’re ready to step on the gas and scale your revenue engine and you don’t have a great answer and aren’t sure how to get to one.

But don’t wait until you’re waking up in the middle of the night to hire a CRO. Instead, use this simple process to build some consistency in your sales team and set yourself up to scale rapidly when the time comes.

Building a Sales Team: From “Whiteboard” to “PDF”

There is a framework we learned from one of our original investors at Return Path, Greg Sands. Greg always talked about the evolution of an enterprise selling process as going from “selling on whiteboard, to Powerpoint, to PDF.” A “Whiteboard” approach to sales is one that is exploratory and conceptual. A “Powerpoint” approach is a sale that requires creativity and tailored pitches, while a “PDF” sale is a standard sale that can be taught quickly to an inexperienced sales rep and used with a high degree of predictability to all customers.

Many startups think that they need to be at the PDF stage quickly but as a startup your goal should not be to deliver a polished, buttoned down and refined final PDF to customers. Your goal should be to start with a mindset of discovery.

Whiteboard Sales Approach

Your initial sales team (maybe the CEO and/or Head of Product) should go to a prospect’s office and literally use a whiteboard, drawing things out (drawing charts, and frameworks, and circles, and arrows, and exclamation points), while you try to understand your potential customer’s problem. You’re creating this with the client because you don’t have a deck yet, much less a PDF. It can be very interactive and engaging selling on a whiteboard and using that very intimate moment to try to develop the right story for your product.

Powerpoint Sales Approach

As you evolve and grow, chances are you’ll have a sales deck and a pitch because you won’t be discovering what the customer needs. You’ll have very refined (and tested) ideas about their needs and maybe you’ll even have customer segments. But a caution here is that what could (and often does) happen is that your deck, your pitch, get modified along the way — for every single pitch. So, if you have four salespeople, each of them has a different version on their laptop, and there’s probably no central organizing body yet that has thought about what the tone and tenor of the brand should be.

This is the “Selling with PowerPoint” stage and it’s here that good, clever, senior, business development-oriented salespeople are most successful because they will create custom pitches for each client based on their learned history of what has and has not worked in other places. You are still miles away from being a sales machine and what you need is a level of sophistication and market understanding that enables you to get to a PDF presentation.

PDF Sales Approach

A PDF is something that’s complete, that can’t be modified or altered, and it ensures that everyone’s speaking the same language. At this point you have the kind of consistency and message and positioning that enable you to be repeatable and scalable. You can hire a new, junior sales rep, train them for a few weeks, hand them a prospect list and a pdf, and have a really good sense of that person’s likely productivity.

Of course, selling by whiteboard — and even PowerPoint — is sufficient to a point in time but if you’re thinking about unleashing your product on a massive scale, then you have to get to the point where you have a very smooth presentation and message that you know resonates with the audience.

You might be thinking that you can get your sales team from whiteboard to PDF quickly, that it’s a matter of understanding the process and then executing it. But the reality is that there is no quick way to get from whiteboard to PDF and it’s not a linear process. You can’t put into your business plan that you’ll spend the first six months selling with whiteboard, the next six months selling with PowerPoint, and the next six months selling with PDF. It’s much more nuanced, there’s a lot of trial and error, a lot of experimentation, and a lot of thinking and rethinking based on customer ideas and feedback. At Return Path, for example, it probably took us somewhere between five to ten years before we got from whiteboard to PDF and it was only after refining our approach and materials that we were able to build a sales machine.  

Obviously, a startup can’t wait the five to ten years to hire a CRO, but even at the “Whiteboard” stage an inquisitive person, excited about your product and customers, could help build and grow a dynamic sales team… and certainly by the “Powerpoint” stage, a strong senior sales leader can make a world of difference — and drive you to the “PDF” stage.

Aug 26 2021

Five Misperceptions of the CCO Role

This post was inspired by Startup CXO and was originally published by Techstars on The Line.

If you’re new to the Chief Customer Officer role, we’d like to share some advice we wish we had learned earlier in our careers. There are a few common misconceptions about customers and the service organization. If you don’t realize these as misperceptions, you can spend a lot of time dealing with issues that are not real, but perceived. We have identified five of these common misperceptions, although we are sure there are more.

Misperception #1: The service organization fully controls churn (customer attrition)

In a lot of organizations you’ll see the service organization be measured solely on customer churn. If you really think about it, there are many elements that come into play that impact churn, including

  • How the customer is sold
  • The quality of the product
  • How easy it is to onboard the customer
  • How easy it is to use the product
  • How easy it is for the customer to understand what kind of value they’re getting out of the product

Of course, the service functions do have a critical role, but they’re not the only functions in a company that impact churn. The responsibility for churn also lies with sales, engineering, marketing, and other teams. One reason why you need a C-level senior person in charge of all service operations is because you need someone who understands the customer experience broadly and that person has to work cross-functionally to ensure customer retention.

Misperception #2: The service organization is just a cost center

In many businesses, if a function isn’t generating new revenue, it’s seen as “second class.” From our perspective revenue retained is revenue gained and the service organization has a big impact on retaining revenue. In addition, the account management portion of a service organization is often in charge of up-sale and cross-sale opportunities which can be huge areas of growth. CCOs should work within their company to alter that misperception of service as a cost center because the service organization can have a huge impact on revenues.

Misperception #3: Service teams should focus on responding to defections

I’ve recently found a situation where the customer success team is built to focus on the clients who have raised their hand and said, “I want to leave.” This reactive approach drives low job satisfaction and isn’t the “best and highest use” of a service team’s time. By the time a customer is frustrated enough, or isn’t seeing the value enough, that they want to leave — you’ve missed a window of opportunity. The right focus should be proactively helping customers reach their desired business objectives. If you can do that, most customers will stay. That’s the theory behind the rise of the customer success team and that’s what great companies are doing today.

Misperception #4: Service’s job is to “paper over” gaps in the product

There is a widespread practice of covering for product issues by throwing service at the problem. That certainly can work, but it’s not optimal. The superior approach is to focus the service team on becoming a trusted advisor for customers, helping those customers achieve their desired outcomes. To do that, the CCO will have to work cross-functionally with the product team, the marketing team, and the sales team to drive a more friction-free customer experience.

Misperception #5: Service is boring and tactical

There is a wide-spread misperception that working in the service organization is boring. It’s mundane, it’s tactical, it doesn’t appeal to people who think strategy is grander than tactics. I don’t agree with that at all. A great service organization starts with a strategy. It starts with an understanding of customer segmentation. It includes thinking about the different customer personas and how to define an appropriate and valuable customer experience. That core strategy actually takes a while to develop. Once the strategy takes hold, it is core to driving retention over time. And, while a lot of people perceive that the service organization jobs are boring, or just answering trouble tickets or reacting to client problems, that’s not the whole role. It is a strategic role as well. 

The Chief Customer Officer has a big impact on the success of a company, especially startups and scaleups, and their function touches nearly every aspect of a company. To give your company the best chance of scaling, the Chief Customer Officer should understand, pinpoint, and manage misperceptions so that they can devote their time, energy, and resources to the real problems that help customers.

Aug 19 2021

Startup Boards eBook: How to Succeed in Your First Board Role

In addition to our work on helping CEOs understand board-building best practices, which I posted about last week, I’ve spent the past several months publishing a second series of blog posts to help current and aspiring directors (really, any senior executive!) understand the behind-the-scenes details of private company board service. This second series is also now an eBook and its content will also feature in the upcoming second edition of Startup Boards that I’m collaborating on with Brad Feld and Mahendra Ramsinghani.

When Bolster published the findings of our Board Benchmarking study, we revealed that 4 out of 5 seats on private company boards today are held by individuals who are white, and 86% of director seats are held by men.

And we also learned that 2 out of 3 CEOs are open to bringing on first-time directors to their boards, largely to help add some much-needed diversity to the most senior ranks of corporate service. To assist current and aspiring board directors out there, we decided to aggregate our team’s collective brainpower to shed light on how to get recruited for a board role, what to expect once you’re there, and how to make an impact.

You can see the full list of blog posts here:

You can download all of these in an eBook, How to Succeed in Your First Board Role, from the Bolster web site.

We hope this book helps inspire and empower you on your own journey as a board director. And if you’d like to get access to more exclusive content like this and be considered for a board role in the future, you can sign up as a Bolster member here.

Aug 12 2021

Startup Boards eBook: How to Build Your Board

Over the past several months, I’ve published two series of posts on the Bolster blog about Boards. The first series is designed to help CEOs better understand how to build, diversify, and scale their boards of directors. I’ll write about the second one next week. Both series of posts will feature in the second edition of Startup Boards, a book originally published in 2014 by Brad Feld and Mahendra Ramsinghani. The second edition, which is also co-authored by me, will be out late this year or early next year.

As I’ve gone about building our business at Bolster, including leading several dozen board searches for companies of all sizes and stages from pre-revenue to public, I’ve noticed that there are still a lot of questions among company leaders about board-building best practices. Without a lot of documentation and analysis about private company boards, most startup CEOs learn about building and managing boards through trial and error. As a result, this critical component of corporate governance is often under-utilized. Directors’ skills and networks are under-leveraged, term lengths are rarely re-negotiated, and board diversity becomes an afterthought.

This is why I set out to publish a comprehensive look at building boards, written from one CEO to another. You can read the full series here:

The team at Bolster also compiled all of these posts into an eBook you can download by clicking on this link, entitled How to Build Your Board. No matter where you are in your journey as a CEO or company leader, I hope this is a resource and reference for you to look back on over time.

By the way – if you’d like to get access to more content like this or start a search for an independent director for your own board, you can sign up as a Bolster client here.

Aug 5 2021

Lessons from the Pandemic: a Mid-Mortem

It feels like it may be a bit premature to write a post with this title here in the summer of 2021. Even as vaccines are rolling out fairly quickly, the combination of the Delta mutation of the COVID-19 virus and a bizarrely large anti-vaccine movement in the US, plus slower vaccine roll-outs in other parts of the world, are causing yet another spike in infections. 

However, I read Michael Lewis’s The Premonition last week, a bit of a “mid-mortem” on the Pandemic, and it got me thinking about what lessons we as a society have learned in these past 18 months, and how they can be applied to entrepreneurs and startups. I am particularly drawing on the few weeks I was deeply engaged with the State of Colorado’s COVID response effort, which I blogged about here (this is the 7th post in the series, but it has links to all the prior posts in order).

Here are a few top of mind thoughts. 

First, entrepreneurial skills can be applied to a wide range of society’s challenges.  The core skills of founders and entrepreneurs are vision, leadership/inspiration/mobilization of teams, and a fearlessness about trying things and then seizing on the ones that work and rapidly discarding the ones that don’t, quickly absorbing learnings along the way. If you look broadly at the world’s response to the Pandemic, and at Colorado’s response as a microcosm, you can see that the jurisdictions and organizations that employed those types of skills were the ones that did the best job with their response. The ones that flailed around — unclear vision, lurching from plan to plan and message to message, pandering to people instead of following the science, sticking with things that didn’t make sense — those folks got it wrong and saw more infections, hospitalizations, and deaths. 

Second, parachuting in and out of leadership roles really works but is a little bit unsatisfying. I think that, even in a short period of time, I got a lot of good work done helping organize and stand up the IRT in Colorado. It was very much an “interim CEO” job, not unlike a lot of the roles we place at Bolster. Without a ton of context around the organization I was joining, I still had an impact. The unsatisfying part is more about me as the exec than it is about the organization, though. I’m so used to being around for the long haul to see the impact of my work that I found myself pinging Sarah, who took over the leadership of the group after I left, Brad, and Kacey and Kyle on the teamfor a few weeks just to find out what was going on and what had become of Plan X or Idea Y. 

Third, I came to appreciate something that I used to rail against in the business world, or at least came to appreciate an alternative to it. I frequently will say something like “don’t solve the same problem four different ways,” almost always in response to people facing a big hole in the organization and trying to hire four different people to fill the hole, when likely one hire will do (or at least one for starters). But what Michael Lewis calls the “Swiss cheese defense” or Targeted Layered Containment (TLC) that worked pretty well as defense and mitigation against the virus while there was no vaccine totally worked. He calls it the Swiss cheese defense because, like a slice of Swiss cheese, each layer of defense has holes in it, but if you line up several slices of Swiss cheese just right, you can’t see any of the holes. Some masking here, some quarantining there, couple closures over there, a lot of rapid testing, some working from home where possible, some therapeutics – and voila – you can blunt the impact of a pandemic without a vaccine. The same must be true for complex problems in business. I am going to amend my approach to consider that alternative next time I have a relevant situation. 

Fourth, blunt instruments and one size fits all solutions to complex problems (especially in this situation, with multiple population types in multiple geographies) — even those with good intentions — can’t work, drive all sorts of unintended consequences, with a lack of feedback loops can make situations worse or at least frustrating. Nationwide or even statewide rules, quite frankly even county-wide rules, don’t necessarily make sense in a world of hot spots and cool spots. Statewide regulations for schools when districts are hyper local and funded and physically structured completely differently, don’t always make sense. There are definitely some comparables in the business world here – you’d never want, for example, to compensate people across all geographies globally on the identical scale, since different markets have different standards, norms, and costs of living. 

Finally, I am left with the difficult question of why all the preparation and forethought put into pandemic response seemed to fail so miserably in the US, when several nations who were far worse equipped to handle it in theory did so much better in reality. I am struggling to come up with an answer other than the combination of the general American theme of personal choice and liberty meeting the insanely toxic and polarizing swirl of politics and media that has made everything in our country go haywire lately. Big government incompetence in general, and failures of national leadership on this issue, also factor in heavily.  I also gather from Michael Lewis that the transition from one administration to another frequently involves a massive loss of institutional knowledge which can’t help. Of all these, failure of strong leadership stands out in my mind. 

The lesson for startups from this last point is important. Leadership matters. Eisenhower once said something to the effect that “plans are nothing but planning is everything.”  The thoughtfulness, thorough planning, communication and inspiration, and institutional knowledge that come from effective leadership matter a lot in executing and growing a startup, because you literally never know what COVID-analog crisis is lurking quietly around the corner waiting to pounce on your startup and threaten its very existence.