I’ve been uncharacteristically quiet since April (I still hate non-competes and while I respect the right of the Chamber of Commerce to sue the FTC, I hope common sense prevails). Between then and now, we switched things up at Bolster, and my co-founder Cathy Hawley is now the CEO. Things are great there, and if you need any executive search help (Director to C-level or Board/Advisory/Fractional), let me know.

I’ve been hard at work on a passion project while I’ve been between things professionally, and I’m excited this week to announce the launch of my new podcast mini-series, Country Over Self: Defining Moments in American History. That link is to the web site where you can see the whole plan for the series.

Whether or not you’re a US History nerd like me, I hope you enjoy the Country Over Self podcast, especially since what I do is basically take a CEO lens to the whole subject.

Here are the links to the show on the three major podcast platforms and YouTube if you want a video option:

• Apple
• Spotify
• Amazon
• Youtube

I am taking a very nonpartisan approach to analyzing critical moments in American history to tell some of our shared stories and highlight some of our shared values as a country to play some small part in bringing us back together as a nation. This is NOT a political podcast, but it IS at least in part a response to this divisive election season and the environment the past 10-20 years, partly the product of a lifelong obsession with the American Presidency. Somehow, and I don’t know how this is possible, I’ve never blogged about it, but Brad has. My bibliography has grown a lot since then, but this is a good start.

My trailer (Episide 0, about 3 minutes long) is live as well as E1, on LBJ, which I just dropped today, all on all those platform show links above. I’ll drop 1-2 episodes a week until the end of the year when I’ll wrap up the series. I am so lucky to have been able interview the historians I have to produce this.

I am closing in some new CEO opportunties, so I’ll be back with more once those shape up.

This is another big week for us at Bolster. On the heels of the announcement we made last month about our Series B financing, we are now announcing the launch of a new program called Bolster Prime and a new venture capital fund called Bolster Ventures. These are important steps in Bolster’s evolution and in the fulfillment of our mission, what we call internally our “Big Idea,” which is to empower the innovation economy.  

The roots of Bolster Prime and Bolster Ventures pre-date the founding of Bolster. In our prior lives, the Bolster founders worked together to scale up a business called Return Path and also 

worked as advisors and mentors to numerous early stage founders and startups. One of the things we noted in our very first post, now part of the About Us section of Bolster.com, was:

After exiting Return Path [the company where our founding team worked for many years], we wanted to do for others what we did for each other as a seasoned executive team. We wanted to know: “How could we help other CEOs, executives and boards bolster themselves to go the distance and scale with their organizations?”

While the founding team was exploring potential business opportunities that allowed us to make a bigger impact on the world, Silicon Valley Bank and High Alpha Innovation were together envisioning a platform to help VC-backed portfolio companies more effectively navigate the complex world of executive talent needs. When our three groups came together, we realized we shared a vision to build a company that puts people first in all aspects to drive high-growth businesses.

I’ve never written before about those other “potential business opportunities” that our team was exploring along with our prior investment syndicate, Fred Wilson from Union Square Ventures, Greg Sands from Costanoa Ventures, and Brad Feld from Foundry. The one our team was particularly excited about was a concept we were calling at the time “Venture Acceleration Partners.” The key points in the pitch deck we created were:

• There is a gap in the market of investors adding “management” value to portfolio companies between Accelerators/Incubators/Studios at the low end and Private Equity firms and very large VCs at the high end. What about the middle?
  
• “The middle” consists of venture-backed companies that are neither early stage nor mature. They are typically founder-led, often by a first-time CEO with new or incomplete management teams who need a lot of mentorship/development, and with a diversified cap table of firms that don’t own operating or consulting practices to help guide the scaling process.
  
• These companies tend to have consistent and stage-unique challenges around scaling execution across every aspect of the business.
  
• By creating an advisory firm made up of seasoned operators, we can quickly identify the risk areas and provide mentoring, guidance and execution to management teams for defined periods of time to keep them on the right track and increase their companies’ performance.
  
• We want to create a firm that has enough skin in the game to have long-term relationships with management teams…and that doesn’t charge (much) for services because incentives are aligned as a co-investor.

Our original deck envisioned a firm that was sort of a hybrid of a “McKinsey for startups” and a venture investor. When I shared that pitch deck (and two other ones I’ll save for another day), with my long-time friend Scott Dorsey from High Alpha, he responded by sharing with me a related pitch deck he was working on with corporate partner Silicon Valley Bank out of the High Alpha Studio for a talent marketplace. We immediately looked at each other and said “we should put all of these ideas together with this founding team, High Alpha and SVB, and the Return Path investors, and change the way startups connect with talent.” That’s what we did, and we almost immediately started building the first part of the Bolster business, which was the talent marketplace.

About six months into our journey building Bolster, I was talking to Brad and reminded him that I was interested in bringing the Venture Acceleration idea to life now that we had a vibrant talent marketplace up and running at Bolster. 

Standing up a new program of this magnitude with limited resources at the same time as building a new venture capital firm from the ground up, on top of a still pretty brand new startup – that felt like a tall order, even for a large and senior founding team like ours. We needed another senior leader to join our team. 

Brad’s visceral response in this conversation was a very clear, “you should hire Jenny.” Enter Jenny Lawton. Jenny is someone I’d known peripherally for many years as a mutual friend and colleague of Brad, but we weren’t particularly close. We agreed to meet for breakfast at a diner halfway between our houses at a time in the pandemic when there wasn’t a whole lot of in-person meetings going on. 

As Jenny’s written about this week, it was the right call at the right time – we had a full meeting of the minds about the role mentorship plays in supporting entrepreneurs, the unmet needs of entrepreneurs even with all the support out there from accelerators and investors, and the desire that both of us had here in the back half of our careers to, as Steve Jobs would say, “make a dent in the universe.” Jenny’s experience as a multiple-time senior executive and startup advisor (including four years as the COO of Techstars) was a perfect match for us. She joined our team pretty quickly, first fractionally (the Bolster way, right?), then full-time in the middle of 2021. 

And the rest, as they say, is history. Working as part of the Bolster leadership team this past year, Jenny has spearheaded the creation of Bolster Prime, from selling and mentoring the first few clients personally, to designing the curriculum and programmatic learning, to figuring out the right positioning and pricing to developing the recruiting strategy for the program. We’ve worked together and along with the rest of the team at Bolster to bring in an amazingly talented group of experienced former and current CEOs and other senior operators as our first group of mentors.  Any entrepreneur would be lucky to have one of these mentors in their corner. We’ve now raised a venture capital fund as first-time fund managers from our own investors and our program’s mentors, all of whom believe in the power of Bolster as the next generation platform to help empower the innovation economy. 

Most good ideas swim in a sea of comparables. There are now a handful of other firms out there that combine advice for entrepreneurs with capital. But we believe our model, with thousands of Bolster Member CXOs already on board, is unique. Bolster Prime and Bolster Ventures, powered by Bolster’s on-demand talent marketplace, is here to help early stage founders reimagine the way they scale up their leadership teams, their boards, and themselves. We are changing the way the startup game is played. Come take a look and see what’s in it for you.

This is the third post in the series. The first one When to hire your first CPO is here and What does Great Look Like in a CPO is here)

If you’ve been following my previous blog posts on the Chief People Officer you have figured out when to hire one and what to look for in getting a great one but even so, you can’t just assume that your Chief People Officer is going to be able to scale with your company. I have found that Chief People Officers who aren’t scaling well past the startup stage are the ones who typically operate in the following ways.

First, a CPO might not be able to scale if they are overly focused on the transactional aspects of the job.  Don’t get me wrong, there are many transactional elements to HR – payroll, benefits, systems, process, etc. – and they all have to go well or employees freak out.  But the Chief People Officer who spends all their time on these issues isn’t delegating well, isn’t building a machine, isn’t building scalable people and processes to flawlessly and efficiently handle the details. This inability to delegate may be a lack of self-confidence or a lack of trust that others can step up, but either way it’s a telltale red flag if a CPO is mostly focused on the transactional aspects of the role and not the strategic aspects.

Another sign is if the CPO won’t speak up in executive team meetings.  Chief People Officers have every right and entitlement to hold opinions about the company’s strategy, products, operations, and financials.  The good ones do – and they’re not shy about speaking up publicly about them.  The weaker ones, or the ones who are in a bit over their heads, don’t speak up, don’t challenge others, because they either haven’t taken the time to learn and formulate those opinions, or because they don’t have enough confidence among their peers to voice them. The CPO needs to be a leader among leaders and any hesitancy to fully participate with their peers is a sign to me that maybe they’re not scaling, not developing their own personal and executive skills.

Another sign I’ve seen that the CPO isn’t scaling is if they have trouble managing/leading their own team.  Since a good Chief People Officer is one who spends time coaching all the other leaders in your business on how to be effective leaders, it’s particularly worrisome when they themselves are not an effective leader, especially with what is usually a relatively small function.  This is a classic case of the cobbler’s children walking around barefoot, and it’s a sign of trouble for your HR leader.

None of these signs by themselves is particularly worrisome to me, but if you have a Chief People Officer who is transactional, doesn’t speak up, and has morale or turnover issues in their own team, you’ve got big problems. The CPO is critical to the entire organization so if you find that your CPO is exhibiting several of these traits you’ll need to address it quickly—either through coaching, by bringing on a fractional executive to mentor, or by replacing the CPO. Often, coaching and fractional approaches are more cost-effective, less disruptive to the company, and lead to great results. Ignoring it is the worst approach for this important position.

(You can find this post on the Bolster Blog here)

I wrote a little bit about the experience of being a multi-time founder in this post where I talked about the value of things like a hand-picked team, hand-picked cap table, experience that drives efficient execution, and starting with a clean slate. The second lap around the track (and third, and fourth) is really different from the first lap.

Based on what we do at Bolster, and my role currently, I spend a lot of time meeting with CEOs of all sizes and stages and sectors of company, as they’re all clients or prospects or people I’m coaching. Lately, I’ve noticed a distinct set of work and behaviors and desires among CEOs who are multi-time founders and operators that is different from those same things in first-time founders. Not every single multi-time founder has every single one of these traits, but they all have a majority of them and form a pretty common pattern. I’ve noticed this with non-profit founders as well as for-profit ones.

• They have an Easier Time Recruiting team members and investors. That may sound obvious, but there are significant benefits to it. They also tend to have Much Cleaner Cap Tables, because they lived the horrors of a messy cap table when they exited their last company without thinking about that topic ahead of time!
  
• They have a Big Vision. Once you’ve had an exit, whether successful or not or somewhere in between, you don’t want to focus on something niche. You want to go all-in on a big problem.
  
• They are interested in creating Portfolio Effect. A number of repeat founders want to start multiple business at the same time, are actually doing it, or are creating some kind of studio model that creates multiple businesses. Once you have a big team, a track record with investors, and a field of deep expertise, it’s interesting to think about creating multiple related paths (and hedges) to success.
  
• They are driving to be Efficient in Execution and Find Leverage wherever they can. One multi-time founder I talked to a few weeks ago was bragging to me about how few people he has in his finance team. At Bolster, our objective is to build a big business on a small team, looking for opportunities to use our own network of fractional and project-based team members wherever possible.
  
• They are Impatient for Progress. While being mindful that good software takes time to build no matter how many engineers you hire, repeat founders tend to have fleshed out their vision a couple layers deep and are always eager to be 6 months ahead of where they are in terms of execution, which leads me to the next point, that…
  
• They are equally Impatient for Success (or Failure). More than just wanting to be 6 months ahead of where they are in seeing their vision come to life, they want to get to “an answer” as soon as possible. No one likes wasting time, but when you’re on your second or third company, you value your time differently. As a friend of mine says in a sales context, “The best answer you can get from a prospect is ‘yes’ – the second best answer you can get is a fast ‘no’.” The same logic applies to success in your nth startup. Succeed or Fail – you want to find out fast.
  
• They are Calm and Comfortable in Their Own Skin. At this stage in the game, repeat founders are more relaxed. They know their strengths and weaknesses and have no problem bringing in people to shore those things up. They know that if things don’t work out with this one, there’s more to life.
  
• They are stronger at Self Management. They are more efficient. They exercise more. They sleep more. They spend more time with family and friends. They work fewer hours.

Anyone else ever notice these traits, or others, in repeat founders?

One of the CEOs I mentor asked me the other day asked me this question:

I need to start making my organization think differently – more like a startup that needs to scale and less like a project. People need to start doing more specific jobs and not swarm all over everything. How do I get people to “get” this without freaking out?

Every CEO faces dilemmas like this all the time.

One of my management mantras over the years has been, “You have to bring people along for the ride.” Fundamentally, that means two things. I’ll write about one of them here today and save the other for next week.

First, bringing people along for the ride means you have to involve the people in the organization in the origins and design of the change you’re seeking to drive.

Let’s face it. No one really likes change. But what people really don’t like is change being IMPOSED ON THEM, especially where THEY DON’T UNDERSTAND WHY.

Without being disingenuous, you as a leader can set the stage for others in your organization helping you with changes — even if you generally know the changes you want to drive. Bring people together. Talk about the challenges you see that are related to the solution you’re contemplating. Get people talking, brainstorming, grabbing post-its and whiteboard pens. Talk a little bit – bring in your perspective and help shape the discussion. But also listen closely and be open to people’s ideas and let those shape the outcome as well.

Then, bring people back for a second and third meeting to then react to some of your idea distillation and even straw man plans. You’ll find that process not only produces a better solution but also makes people comfortable with the solution, because you’ve added more transparency to the equation and brought people along for the ride. Nothing done in the vacuum of the CEO’s mind achieves this same level of impact.

More thoughts on this to come in some related posts over the next couple of weeks around some geeky sounding terms like The Ladder of Inference, Inquiry vs. Advocacy, and Double Loop Learning. Next week’s post will be about how to think about transitions and the way to lead people through them once you’ve involved them in creating the transition. Its link won’t be live until April 20, but it’s here for future reference.

Good Meeting Behavior

I've been in meetings with large groups of people at big companies where they're all on laptops the whole meeting, no one makes any eye contact with the speaker/facilitator, and it's hard to get a pulse out of the group as a result.

I almost entirely stopped bringing laptops and smartphones into business meetings a few years back.  There's nothing I find more irritating than when other people are using them when it's my meeting.  Even if they're taking notes, I never know if they're really taking notes or sneaking a peek at email.  And in my experience, people who are on laptops and phones in meetings, whatever they're doing on those devices and however good they are at multi-tasking, aren't paying as close attention to the meeting as the other people in the room. 

What I do instead is take notes on paper and spend 2 minutes after the meeting handling whatever data entry I need to handle on my computer.

I was very excited to see Brad's post about how he is now going to take paper notes in Board meetings rather than use his smartphone and be tempted to check email (and otherwise be distracted).  Everyone should do this for every meeting.  Board meetings are important examples, but they're not alone.  It's just good meeting behavior.  If you have other things to do, step out of the meeting and do them.

As I mentioned in a previous post, I write a column for The Magill Report, the new venture by Ken Magill, previously of Direct magazine and even more previously DMNews. I share the column with my colleagues Jack Sinclair and George Bilbrey and we cover how to approach the business of email marketing, thoughts on the future of email and other digital technologies, and more general articles on company-building in the online industry – all from the perspective of an entrepreneur. I recently posted George’s column on Staying Innovative as Your Business Grows (Part One). Below is a re-post of George’s second part of that column from this week, which I think my OnlyOnce readers will enjoy.

Guest Post: Staying Innovative as Your Business Grows (Part Two)

By George Bilbrey
Last month, as part of the Online Entrepreneur column, I shared some of Return Path’s organizational techniques we use to stay innovative as we grow. In this article, I’ll talk about the process we’re using in our product management-and-development teams to stay innovative.

The Innovation Process at Return Path
As we grew bigger, we decided to formalize our process for bringing new products to market. In our early days we brought a lot of new products to market with less formal process but also with more limited resources. We did well innovating one product at a time without that kind of process largely because we had a group of experienced team members. As the team grew, we knew we had to be more systematic about how we innovated to get less experienced product managers and developers up to speed and having an impact quickly.

We had a few key objectives when designing the process:

• We wanted to fail fast – We had a lot of new product ideas that seemed like good ones. We wanted a process that allowed us to quickly determine which ideas were actually good.

• We wanted to get substantial customer feedback into the process early – We’d always involved clients in new product decisions, but generally only at the “concept” phase. So we’d ask something like “Would you like it if we could do this thing for you?” which often elicited a “Sure, sounds cool.” And then we’d go off and build it. We wanted a process that instead would let us get feedback on features, function, service levels and pricing as we were going so we could modify and adjust what we were building based on that iterative feedback.

• We wanted to make sure we could sell what we could build before we spent a lot of time building it – We’d had a few “build it and they will come” projects in the past where the customers didn’t come. This is where the ongoing feedback was crucial.

The Process
We stole a lot of our process from some of the leading thinkers in the “Lean Startup” space – particularly Gary Blanks’ Four Steps to the Epiphany and Randy Komisar’s Getting to Plan B. The still-evolving process we developed has four stages:

Stage 1: Confirm Need

Key Elements

• Understand economic value and size of problem through intense client Interaction
• Briefly define the size of opportunity and rough feasibility estimate – maybe with basic mockups
• Key Question: Is the need valid? If yes, go on. If no, abandon project or re-work the value proposition.

Stage 2: Develop Concept

Key Elements

• Create a high fidelity prototype of product and have clients review both concept and pricing model
• Where applicable, use data analysis to test feasibility of product concept
• Draft a more detailed estimate of effort and attractiveness, basically a business model
• Key Question: Is the concept Valid? If yes, go on. If no, abandon project.

Stage 3: Pilot

Key Elements

• Build “minimum viable product” and sell (or free beta test with agreed to post beta price) with intense client interaction and feedback
• Develop a marketing and sales approach
• Develop a support approach
• Update the business model with incremental investment requirements
• Preparation of data for case studies
• Key Question: Is project feasible? If yes, go on. If no, abandon project or go back to an earlier stage and re-work the concept.

Stage 4: Full Development and Launch

Key Elements

• Take client feedback from Pilot and apply to General Availability product
• Create support tools required
• Create sales collateral, white papers, lead generation programs, case studies and PR plan.
• Train internal teams to sell and service.
• Update business model with incremental investment required
• Go forth and prosper

There are a several things to note about this process that we’ve found to be particularly useful:

• A high fidelity prototype is the key to getting great customer feedback – You get more quality feedback when you show them something that looks like the envisioned end product than talking to them about the concept. Our prototypes are not functional (they don’t pull from the databases that sit behind them) but are very realistic HTML mockups of most products.

• Selling the minimum viable product (MVP) is where the rubber meets the road – We have learned the most about salability and support requirements of new products by building an MVP product and trying to sell it.

• Test “What must be true?” during the “Develop Concept” and “Pilot Phases” – When you start developing a new product, you need to know the high risk things that must be true (e.g., if you’re planning to sell through a channel, the channel must be willing and able to sell). We make a list of those things that must be true and track those in weekly team meetings.

• This is a very cross functional process and should have a dedicated team – This kind of work cannot be done off the side of your desk. The team needs to be focused just on the new product.

While not without bumps, our team has found this process very successful in allowing us to stay nimble even as we become a much larger organization. As I mentioned in Part 1, our goal is really to leverage the strengths of a big company while not losing the many advantages of smaller, more flexible organizations.

The Gift of Insight

Jonathan Schwartz has a great post entitled “Every Customer Visit is a Lesson.” It’s so true…if you want to give yourself a gift this holiday season, give yourself the gift of insight and spend some time in the market with a few of your top customers or prospects.  I’ve always found that to be one of the most valuable ways to shape the business, both strategically and operationally.

One of the most vivid memories I have to illustrate this concept is a meeting that I had with Crate and Barrel, a prospect, in the very early days of Return Path, back in 2000 or 2001.  I went in with my colleague Sophie Miller, and with a number of product sales specialists from our reseller, DoubleClick, for an all-day session with C&B’s online marketing team.  We collectively were pitching everything, possibly including the kitchen sink — ad serving through DART, buying online media through the DoubleClick Network, using Abacus to expand the reach of their catalog, sending email through DARTMail, renting email lists through DoubleClick’s email list business, oh yes, and using Return Path’s ECOA service to keep their email database clean.

The meeting was a mess, and as far as I can tell, it didn’t really lead to any meaningful business, either for us or for DoubleClick.  I learned two things in this call the hard way, but both were incredibly valuable lessons that continue to shape our business today.

First, we created massive confusion by bringing multiple sales people in to each present a specific product to the customer, rather than sending in one senior, consultative sales person to present a holistic digital marketing solution.  Picture yourself as the head of e-commerce for a major retailer, expecting an insightful day with the leading vendor in the space…then walking into the meeting and seeing that vendor’s SEVEN different sales people introducing themselves to each other!  It was a mess.  Since then, we have tried hard (and I think DoubleClick has as well) to run with a single sales force organized around the customer, not organized around our own products.

Second, we discovered that the original version of our flagship ECOA product (which was still in beta at the time) had a couple of flaws in the business model that were probably going to make it a non-starter in the retail/catalog vertical.  We also learned, happily, that the client loved the concept, but there were some details in the original product that had to be fixed if we were ever going to get traction with key customers in that key segment.  We fixed these problems and were able to successfully re-launch ECOA later that year, but more important, we now stay much closer to our customers as we develop new products and features so we make sure concepts are more firmly market tested before they head into development.

There are many more examples of this Gift of Insight, which I’ll share in future posts.  Happy Holidays!

What Makes an Awesome Board Member

(This post was requested by my long-time Board member Brad Feld and is also running concurrently on his blog today)

I’ve written a bunch of posts over the years about how I manage my Board at Return Path.  And I think part of having awesome Board members is managing them well – giving transparent information, well organized, with enough lead time before a meeting; running great and engaging meetings; mixing social time with business time; and being a Board member yourself at some other organization so you see the other side of the equation.  All those topics are covered in more detail in the following posts:  Why I Love My Board, Part II, The Good, The Board, and The Ugly, and Powerpointless.

But by far the best way to make sure you have an awesome board is to start by having awesome Board members.  I’ve had about 15 Board members over the years, some far better than others.  Here are my top 5 things that make an awesome Board member, and my interview/vetting process for Board members.

Top 5 things that make an awesome Board member:

• They are prepared and keep commitments.  They show up to all meetings.  They show up on time and don’t leave early.  They do their homework.  The are fully present and don’t do email during meetings
• They speak their minds.  They have no fear of bringing up an uncomfortable topic during a meeting, even if it impacts someone in the room.  They do not come up to you after a meeting and tell you what they really think.  I had a Board member once tell my entire management team that he thought I needed to be better at firing executives more quickly!
• They build independent relationships.  They get to know each other and see each other outside of your meetings.  They get to know inviduals on your management team and talk to them on occasion as well.  None of this communication goes through you
• They are resource rich.  I’ve had some directors who are one-trick or two-trick ponies with their advice.  After their third or fourth meeting, they have nothing new to add.  Board members should be able to pull from years of experience and adapt that experience to your situations on a flexible and dynamic basis
• They are strategically engaged but operationally distant.   This may vary by stage of company and the needs of your own team, but I find that even Board members who are talented operators have a hard time parachuting into any given situation and being super useful.  Getting their operational help requires a lot of regular engagement on a specific issue or area.  But they must be strategically engaged and understand the fundamental dynamics and drivers of your business – economics, competition, ecosystem, and the like

My interview/vetting process for Board members:

• Take the process as seriously as you take building your executive team – both in terms of your time and in terms of how you think about the overall composition of the Board, not just a given Board member
• Source broadly, get a lot of referrals from disparate sources, reach high
• Interview many people, always face to face and usually multiple times for finalists.  Also for finalists, have a few other Board members conduct interviews as well
• Check references thoroughly and across a few different vectors
• Have a finalist or two attend a Board meeting so you and they can examine the fit firsthand.  Give the prospective Board member extra time to read materials and offer your time to answer questions before the meeting.  You’ll get a good first-hand sense of a lot of the above Top 5 items this way
• Have no fear of rejecting them.  Even if you like them.  Even if they are a stretch and someone you consider to be a business hero or mentor.  Even after you’ve already put them on the Board (and yes, even if they’re a VC).  This is your inner circle, and getting this group right is one of the most important things you can do for your company

I asked my exec team for their own take on what makes an awesome Board member.  Here are some quick snippets from them where they didn’t overlap with mine (with only two inside jokes that I couldn’t resist putting up for the Board):

• Ethical and high integrity in their own jobs and lives
• Comes with an opinion
• Thinking about what will happen next in the business and getting management to think ahead
• Call out your blind spots
• Remembering to thank you and calling out what’s right
• Role modeling for your expectations of your own management team – Do your prep, show up, be fully engaged, be brilliant/transparent/critical/constructive and creative.  Then get out of our way
• Offer tough love…Unfettered, constructive guidance – not just what we want to hear
• Pattern matching:  they have an ability to map a situation we have to a problem/solution at other companies that they’ve been involved in – we learn from their experience…but ability and willingness to do more than just pattern matching.  To really get into the essence of the issues and help give strategic guidance and suggestions
• Ability to down 2 Shake Shack milkshakes in one sitting
• Colorful and unique metaphors

Disclaimer – I run a private company.  While I’m sure a lot of these things are true for other types of organizations (public companies, non-profits, associations, etc.), the answers may vary.  And even within the realm of private companies, you need to have a Board that fits your style as a CEO and your company’s culture.  That said, the formula above has worked well for me, and if nothing else, is somewhat time tested at this point!

I’ve published two editions of Startup CEO, a sequel called Startup CXO, and am a co-author on the second edition of Startup Boards. We also just (2025) published mini-book versions of Startup CXO specifically for five individual functions, Startup CFO, Startup CRO, Startup CMO, Startup CPO, and Startup CTO.

You’re only a startup CEO once. Do it well with Startup CEO, a “master class in building a business.”

—Dick Costolo, Partner at 01A (Former CEO, Twitter)

Being a startup CEO is a job like no other: it’s difficult, risky, stressful, lonely, and often learned through trial and error. As a startup CEO seeing things for the first time, you’re likely to make mistakes, fail, get things wrong, and feel like you don’t have any control over outcomes.

As a Startup CEO myself, I share my experience, mistakes, and lessons learned as I guided Return Path from a handful of employees and no revenues to over $100 million in revenues and 500 employees.

Startup CEO is not a memoir of Return Path’s 20-year journey but a CEO-focused book that provides first-time CEOs with advice, tools, and approaches for the situations that startup CEOs will face.

You’ll learn:

How to tell your story to new hires, investors, and customers for greater alignment How to create a values-based culture for speed and engagement How to create business and personal operating systems so that you can balance your life and grow your company at the same time How to develop, lead, and leverage your board of directors for greater impact How to ensure that your company is bought, not sold, when you exit

Startup CEO is the field guide every CEO needs throughout the growth of their company and the one I wish I had.

“Startup CXO is an amazing resource for CEOs but also for functional leaders and professionals at any stage of their career.”

– Scott Dorsey, Managing Partner, High Alpha (Former CEO, ExactTarget)

One of the greatest challenges for startup teams is scaling because usually there’s not a blueprint to follow, people are learning their function as they go, and everyone is wearing multiple hats. There can be lots of trial and error, lots of missteps, and lots of valuable time and money squandered as companies scale. My team and I understand the scaling challenges—we’ve been there, and it took us nearly 20 years to scale and achieve a successful exit. Along the way we learned what worked and what didn’t work, and we share these lessons learned in Startup CXO.

Unlike other business books, Startup CXO is designed to help each functional leader understand how their function scales, what to anticipate as they scale, and what things to avoid. Beyond providing function-specific advice, tools, and tactics, Startup CXO is a resource for each team member to learn about the other functions, understand other functional challenges, and get greater clarity on how to collaborate effectively with the other functional leads.

CEOs, Board members, and investors have a book they can consult to pinpoint areas of weakness and learn how to turn those into strengths. Startup CXO has in-depth chapters covering the nine most common functions in startups: finance, people, marketing, sales, customers, business development, product, operations, and privacy. Each functional section has a “CEO to CEO Advice” summary from me on what great looks like for that CXO, signs your CXO isn’t scaling, and how to engage with your CXO.

Startup CXO also has a section on the future of executive work, fractional and interim roles. Written by leading practitioners in the newly emergent fractional executive world, each function is covered with useful tips on how to be a successful fractional executive as well as what to look for and how to manage fractional executives.

A comprehensive guide on creating, growing, and leveraging a board of directors written for CEOs, board members, and people seeking board roles.

The first time many founders see the inside of a board room is when they step in to lead their board. But how do boards work? How should they be structured, managed, and leveraged so that startups can grow, avoid pitfalls, and get the best out of their boards? Authors Brad Feld, Mahendra Ramsinghani, and Matt Blumberg have collectively served on hundreds of startup and scaleup boards over the past 30 years, attended thousands of board meetings, encountered multiple personalities and situations, and seen the good, bad, and ugly of boards.

In Startup Boards: A Field Guide to Building and Leading an Effective Board of Directors, the authors provide seasoned advice and guidance to CEOs, board members, investors, and anyone aspiring to serve on a board. This comprehensive book covers a wide range of topics with relevant tips, tactics, and best practices, including:

• Board fundamentals such as the board’s purpose, legal characteristics, and roles and functions of board members;
• Creating a board including size, composition, roles of VCs and independent directors, what to look for in a director, and how to recruit directors;
• Compensating, onboarding, removing directors, and suggestions on building a diverse board;
• Preparing for and running board meetings;
• The board’s role in transactions including selling a company, buying a company, going public, and going out of business;
• Advice for independent and aspiring directors.

Startup Boards draws on the authors’ experience and includes stories from board members, startup founders, executives, and investors. Any CEO, board member, investor, or executive interested in creating an active, involved, and engaged board should read this book—and keep it handy for reference.

Five new mini-books from Startup CXO, but with new bonus material and an obvious focus on each specific functional area.

Each book has several topics in common – chapters on the nature of an executive’s role, how a fractional person works in that role, how the role works with the leadership team, how to hire that role, how the role works in the beginning of a startup’s life, how the role scales over time, and CEO:CEO advice about managing the role.

In Startup CTO (Technology and Product), the role-specific topics Shawn Nussbaum talks about are The Product Development Leaders, Product Development Culture, Technical Strategy, Proportional Engineering Investment and Managing Technical Debt, Shifting to a New Development Culture, Starting Things, Hiring Product Development Team Members, Increasing the Funnel and Building Diverse Teams, Retaining and Career Pathing People, Hiring and Growing Leaders, Organizing Collaborating with and Motivating Effective Teams, Due Diligence and Lessons Learned from a Sale Process, Selling Your Company, Preparation, and Selling Your Company/Telling the Story.

In Startup CMO, the role-specific topics Nick Badgett and Holly Enneking talk about are Generating Demand for Sales, Supporting the Company’s Culture, Breaking Down Marketing’s Functions, Events, Content & Communication, Product Marketing, Marketing Operations, Sales Development, and Building a Marketing Machine.

In Startup CFO, the role-specific topics Jack Sinclair talks about are Laying the CFO Foundation, Fundraising, Size of Opportunity, Financial Plan, Unit Economics and KPIs, Investor Ecosystem Research, Pricing and Valuation, Due Diligence and Corporate Documentation, Using External Counsel, Operational Accounting, Treasury and Cash Management, Building an In-House Accounting Team, International Operations, Strategic Finance, High Impact Areas for the Startup CFO as Partner, Board and Shareholder Management, Equity, and M&A.

In Startup CRO, the role-specific topics Anita Absey talks about are Hiring the Right People, Profile of Successful Sales People, Compensation, Pipeline, Scaling the Sales Organization, Sales Culture, Sales Process and Methodology, Sales Operating System, Marketing Alignment, Market Assessment & Alignment, Channels, Geographic Expansion, and Packaging & Pricing.

In Startup CPO (HR/People), the role-specific topics Cathy Hawley talks about are Values and Culture, Diversity Equity and Inclusion, Building Your Team, Organizational Design and Operating Systems, Team Development, Leadership Development, Talent and Performance Management, Career Pathing, Role Specific Learning and Development, Employee Engagement, Rewards and Recognition, Reductions in Force, Recruiting, Onboarding, Compensation, People Operations, and Systems.

If you’ve been reading this blog for a long time (amazingly, it is over 16 years old now!), you know that my company and main professional life’s work up to this point, Return Path, was a 1999 vintage email technology company that we sold last year.  I then had a couple other interim leadership roles, first as interim CEO of another tech company in New York, then in March as the founder and interim leader of Colorado’s COVID-19 Innovation Response Team, which I wrote a series of blog posts about (this is the final post in the series, which links to the whole series).

I’ve generally been quiet on OnlyOnce since last year, but I will be picking up the pace of writing in the weeks ahead for a couple of reasons.

First, I’ve teamed up with a few former Return Path colleagues and some amazing investors and partners to start a new company.  We’re still in quasi-stealth mode, so I’m sorry I can’t talk about it much yet, but I will as soon as we publicly launch sometime after Labor Day.  It’s a cool business in a totally different space from Return Path and plays to our team’s interests and skills around people, values, culture, leadership development, and team scalability. I won’t rename this blog OnlyTwice, but there’s definitely a lot to be said for being a second-time founder.

Related to that, I have also been working on a Second Edition to my book from 2013, Startup CEO: A Field Guide to Scaling Up Your Business, which is coming out in a week or two from Wiley & Sons, and which is available for pre-order now.  I will write a series of posts in the coming weeks that talk about the new material in the second edition.  Our team at the new company is also working on a sequel to that book – more to come on that as well.

For now, I am doing great, enjoying life as a brand new Startup CEO once again, and feeling quite privileged and a little guilty for it by being in this weird bubble of my nice home and yard and feeling safely isolated from the pandemic, from economic dislocation, from social protests, and from having to lead a scaled organization through all of that turmoil.