Welcome to the new StartupCEO.com!

I started writing this blog in May of 2004 with an objective of writing about the experience of being a first-time entrepreneur — a startup CEO — inspired by a blog post written by my friend, long-time Board member and mentor Fred Wilson entitled “You’re only a first time CEO once.”  The blog and the receptivity I got along the way from fellow startup CEOs encouraged me to write a book called Startup CEO:  A Field Guide to Scaling Up Your Business, which was originally published in 2013 and then again as a second edition last year in 2020.

Today I am relaunching the blog as StartupCEO.com both to reflect that relevance of that brand as the book continues to get good traction in the startup ecosystem, and to reflect the fact that I’m now on my second startup as CEO, so “Only Once” doesn’t seem so fitting any more.

The web site has a very minimalist design – and I realize many of you read posts on either RSS or email — those will still operate the same as they have been (no new RSS feed).

As I approach the first anniversary of starting our new company, Bolster, where we help startup CEOs scale their teams, themselves, and their boards, I am recommitting to this blog and will try to post at least once a week.  Because there is a lot of overlap between this blog and Bolster’s blog (which I’d encourage you to subscribe to here either by email or RSS), posts will occasionally show up on both blogs, or I’ll put digests of Bolster blog posts here.  

But the Bolster blog will be broader and will also have many additional authors besides me, while this blog will remain distinct about some of the experiences I’m having as a startup CEO.

Backwards

I came to an interesting conclusion about Return Path recently.  We’re building our business backwards, at least according to what I have observed over time as the natural course of events for a startup.  Here are a few examples of what I mean by that.

Most companies build organically for years…then start acquiring others.  We’ve done it backwards.  In the first 9 years of our company’s life, we acquired 8 other businesses (SmartBounce, Veripost, Re-Route, NetCreations, Assurance Systems, GasPedal Consulting, Bonded Sender, Habeas).  Since then, we’ve acquired none.  There are a bunch of reasons why we front loaded M&A:  we were working hard to morph our business model to achieve maximum success during the first internet downturn, we knew how to do it, there was a lot of availability on the sell side at good prices.  And the main reason we’re not doing a lot of it now is that there’s not much else to consolidate in our space, though we’re always on the lookout for interesting adjacencies.

Most companies tighten up their HR policies over time as they get larger.  We’ve gotten looser.  For example, about a year and a half ago, we abolished our vacation policy and now have an “open” system where people are encouraged to take as much as they can take while still getting their jobs done.  Or another example is an internal award system we have that I wrote about years ago here.  When we launched this system, it had all kinds of rules associated with it — who could give to whom, and how often.  Now those rules have faded to black.  I’d guess that most of this “loosening up” over time is a vote of confidence and trust in our team after years of demonstrated success.

Most companies start by investing heavily in product, then focus on investing in sales and marketing.  Here we haven’t exactly gotten it backwards, but we’re not far off.  Two years ago, one of our major company-wide initiatives/priorities was “Product First.”  This year, we decided that the top priority would be “Product Still First.”  The larger we’ve gotten, the more emphasis we’ve placed on product development in terms of resource allocation and visibility.  That doesn’t mean we’re not investing in marketing or the growth our sales team — we are — but our mentality has definitely shifted to make sure we continue to innovate our product set at a rapid clip while still making sure existing products and systems are not only stable but also improving incrementally quickly enough.

I don’t know if there’s a single generalizable root cause as to why we’ve built the company backwards, or if that’s even a fair statement overall.  It might be a sign that my leadership team is maturing, or more likely that we didn’t know what we were doing 11-12 years ago when we got started — but it’s an interesting observation.  I’m not even sure whether to say it’s been good or bad for us, though we’re certainly happy with where we are as a company and what our prospects look like for the foreseeable future.

But it does lead me to wonder what else we should have done years ago that we’re about to get around to!

Holiday Cards c. 2007

Every year, I get a daily flood of business holiday cards on my desk in the second half of December. Some are nice and have notes from people with whom we do business – clients, vendors, partners, and the like. Some are kind of random, and it takes me a while to even figure out who they are from. Occasionally some even come in with no mark identifying from whence they came other than an illegible signature.

And every year, I receive one or two email cards instead of print & post cards, some apologetic about the medium. Until this year.

I think I’ve received about 10-15 cards by email this month. None with an apology. All with the same quality of art/creative as printed cards. It’s great! A good use of the email channel…much less cost…easier overhead for distribution…and of course better for the environment.

I wonder what made 2007 the tipping year for this.

New Del.icio.us for: Tag

As usual the laggard behind Fred and Brad, I just set up a for:mattblumberg tag on del.icio.us.  Feel free to tag away for me!  If you don’t know what this means, you can read either of their postings about it here or here.

The Difference Between Culture and Values

This topic has been bugging me for a while, so I am going to use the writing of this post as a means of working through it. We have a great set of core values here at Return Path. And we also have a great corporate culture, as evidenced by our winning multiple employer of choice awards, including being Fortune Magazine’s #2 best medium-sized workplace in America.

But the two things are different, and they’re often confused. I hear statements all the time, both here and at other companies, like “you can’t do that — it’s not part of our culture,” “I like working there, because the culture is so great,” and “I hope our culture never changes.”  And those statements reveal the disconnect.

Here’s my stab at a definition.  Values guide decision-making and a sense of what’s important and what’s right.  Culture is the collection of business practices, processes, and interactions that make up the work environment.

A company’s values should never really change. They are the bedrock underneath the surface that will be there 10 or 100 years from now.  They are the uncompromising core principles that the company is willing to live and die by, the rules of the game. To pick one value, if you believe in Transparency one day, there’s no way the next day you decide that being Transparent is unimportant. Can a value be changed?  I guess, either a very little bit at a time, slowly like tectonic plates move, or in a sharp blow as if you deliberately took a jackhammer to stone and destroyed something permanently.  One example that comes to mind is that we added a value a couple years back called Think Global, Act Local, when we opened our first couple of international offices.  Or a startup that quickly becomes a huge company might need to modify a value around Scrappiness to make it about Efficiency.  Value changes are few and far between.

If a company’s values are its bedrock, then a company’s culture is the shifting landscape on top of it. Culture is the current embodiment of the values as the needs of the business dictate. Landscapes change over time — sometimes temporarily due to a change in seasons, sometimes permanently due to a storm or a landslide, sometimes even due to human events like commercial development or at the hand of a good gardener.

So what does it mean that culture is the current embodiment of the values as the needs of the business dictate?  Let’s go back to the value of Transparency. When you are 10 people in a room, Transparency means you as CEO may feel compelled to share that you’re thinking about pivoting the product, collect everyone’s point of view on the subject, and make a decision together. When you are 100 people, you probably wouldn’t want to share that thinking with ALL until it’s more baked, you have more of a concrete direction in mind, and you’ve stress tested it with a smaller group, or you risk sending people off in a bunch of different directions without intending to do so. When you are 1,000 employees and public, you might not make that announcement to ALL until it’s orchestrated with your earnings call, but there may be hundreds of employees who know by then. A commitment to Transparency doesn’t mean always sharing everything in your head with everyone the minute it appears as a protean thought.  At 10 people, you can tell everyone why you had to fire Pat – they probably all know, anyway.  At 100 people, that’s unkind to Pat.  At 1,000, it invites a lawsuit.

Or here’s another example.  Take Collaboration as a value.  I think most people would agree that collaboration managed well means that the right people in the organization are involved in producing a piece of work or making a decision, but that collaboration managed poorly means you’re constantly trying to seek consensus.  The culture needs to shift over time in order to make sure the proper safeguards are in place to prevent collaboration from turning into a big pot of consensus goo – and the safeguards required change as organizations scale.  In a small, founder-driven company, it often doesn’t matter as much if the boss makes the decisions.  The value of collaboration can feel like consensus, as they get to air their views and feel like they’re shaping a decision, even though in reality they might not be.  In a larger organization with a wider range of functional specialists managing their own pieces of the organization, the boss doesn’t usually make every major decision, though guys like Ellison, Benioff, Jobs, etc. would disagree with that.  But in order for collaboration to be effective, decisions need to be delegated and appropriate working groups need to be established to be clear on WHO is best equipped to collaborate, and to what extent.  Making these pronouncements could come as feeling very counter-cultural to someone used to having input, when in fact they’re just a new expression of the same value.

I believe that a business whose culture never evolves slowly dies.  Many companies are very dynamic by virtue of growth or scaling, or by being in very dynamic markets even if the company itself is stable in people or product. Even a stable company — think the local hardware store or barber shop — will die if it doesn’t adapt its way of doing business to match the changing norms and consumption patterns in society.

This doesn’t mean that a company’s culture can’t evolve to a point where some employees won’t feel comfortable there any longer. We lost our first employee on the grounds that we had “become too corporate” when we reached the robust size of 25 employees. I think we were the same company in principles that day as we had been when we were 10 people (and today when we are approaching 500), but I understood what that person meant.

My advice to leaders: Don’t cling to every aspect of the way your business works as you scale up. Stick to your core values, but recognize that you need to lead (or at least be ok with) the evolution of your culture, just as you would lead (or be ok with) the evolution of your product. But be sure you’re sticking to your values, and not compromising them just because the organization scales and work patterns need to change.  A leader’s job is to embody the values.  That impacts/produces/guides culture.  But only the foolhardy leaders think they can control culture.

My advice to employees: Distinguish between values and culture if you don’t like something you see going on at work. If it’s a breach of values, you should feel very free to wave your arms and cry foul. But if it’s a shifting of the way work gets done within the company’s values system, give a second thought to how you complain about it before you do so, though note that people can always interpret the same value in different ways.  If you believe in your company’s values, that may be a harder fit to find and therefore more important than getting comfortable with the way those values show up.

Note:  I started writing this by talking about the foundation of a house vs. the house itself, or the house itself vs. the furniture inside it.  That may be a more useful analogy for you.  But hopefully you get the idea.

Book Short:  Culture is King

Joy, Inc.:  How We Built a Workplace People Love, by Richard Sheridan, CEO of Menlo Innovations, was a really good read. Like Remote  which I reviewed a few weeks ago, Joy, Inc. is ostensibly a book about one thing — culture — but is also full of good general advice for CEOs and senior managers.

Also like Remote, the book was written by the founder and CEO of a relatively small firm that is predominately software engineers, so there are some limitations to its specific lessons unless you adapt them to your own environment. Unlike Remote, though, it’s neither preachy nor ranty, so it’s a more pleasant read.  And I suppose fitting of its title, a more joyful read as well. (Interestingly on this comparison, Sheridan has a simple and elegant argument against working remotely in the middle of the book around innovation and collaboration.)

Some of the people-related practices at Sheridan’s company are fascinating and great to read about. In particular, the way the company interviews candidates for development roles is really interesting — more of an audition than an interview, with candidates actually writing code with a development partner, the way the company writes code. Different teams at Return Path interview in different ways, including me for both the exec team and the Board, but one thing I know is that when an interview includes something that is audition-like, the result is much stronger. There are half a dozen more rich examples in the book.

Some of the other quotable lines or concepts in the book include:

• the linkage between scalability with human sustainability (you can’t grow by brute force, you can only grow when people are rested and ready to bring their brain to work)
• “Showcasing your work is accountability in action” (for a million reasons, starting with pride and ending with pride)
• “Trust, accountability, and results — these get you to joy” (whether or not you are a Myers-Briggs J, people do get a bit of a rush out of a job well done)
• “…the fun and frivolity of our whimsically irreverent workplace…” (who doesn’t want to work for THAT company?)
• “When even your vendors want to align with your culture, you know you’re on the right path” (how you treat people is how you treat PEOPLE, not just clients, not just colleagues)
• “One of the key elements of a joyful culture is having team members who trust one another enough to argue” (if you and I agree on everything, one of us is not needed)
• “The reward is in the attempt” (do you encourage people to fail fast often enough?)
• “Good problems are good problems for the first five minutes. Then they just feel like regular problems until you solve them” (Amen, Brother Sheridan)

The benefits of a joyful culture (at Return Path, we call it a People-First culture) have long been clear to me. As Sheridan says, we try to “create a culture where people want to come to work every day.” Cultures like ours look soft and squishy from the outside, or to people who have grown up in tough, more traditional corporate environments. And to be fair, the challenge with a culture like ours is keeping the right balance of freedom and flexibility on one side and high performance and accountability on the other. But the reality is that most companies struggle with most of the same issues — the new hire that isn’t working out or the long-time employee who isn’t cutting it any more, the critical path project that doesn’t get done on time, the missed quarter or lost client.  As Sheridan notes though, one key benefit of working at a joyful company is that problems get surfaced earlier when they are smaller…and they get solved collaboratively, which produces better results. Another key benefit, of course, is that if you’re going to have the same problems as everyone else, you might as well have fun while you’re dealing with them.

If you don’t love where you work and wish you did, read Joy, Inc. If you love where you work but see your company’s faults and want to improve them, read Joy, Inc. If you are not in either of the above camps, go find another job!

Job 1

The first “new” post in my series of posts about Return Path’s 14 Core Values is, fittingly,

Job 1:  We are all responsible for championing and extending our unique culture as a competitive advantage.

The single most frequently asked question I have gotten internally over the last few years since we grew quickly from 100 employees to 350 has been some variant of “Are you worried about our ability to scale our culture as we hire in so many new people?”  This value is the answer to that question, though the short answer is “no.”

I am not solely responsible for our culture at Return Path. I’m not sure I ever was, even when we were small.  Neither is Angela, our SVP of People.  That said, it was certainly true that I was the main architect and driver of our culture in the really early years of the company’s life.  And I’d add that even up to an employee base of about 100 people, I and a small group of senior or tenured people really shouldered most of the burden of defining and driving and enforcing our culture and values.

But as the business has grown, the amount of responsibility that I and those few others have for the culture has shrunk as a percentage of the total.  It had to, by definition.  And that’s the place where cultures either scale or fall apart.  Companies who are completely dependent on their founder or a small group of old-timers to drive their cultures can’t possibly scale their cultures as their businesses grow.  Five people can be hands on with 100.  Five people can’t be hands on with 500.  The way we’ve been able to scale is that everyone at the company has taken up the mantle of protecting, defending, championing, and extending the culture.  Now we all train new employees in “The RP Way.”  We all call each other out when we fail to live up to our values.  And the result is that we have done a great job of scaling our culture with our business.

I’d also note that there are elements of our culture which have changed or evolved over the last few years as we’ve grown.  That isn’t a bad thing, as I tell old-timers all the time.  If our products stayed the same, we’d be dead in the market.  If our messaging stayed the same, we’d never sell to a new cohort of clients.  If our values stayed the same, we’d be out of step with our own reality.

Finally, this value also folds in another important concept, which is Culture as Competitive Advantage.  In an intellectual capital business like ours (or any on the internet), your business is only as good as your people.  We believe that a great culture brings in the best people, fosters an environment where they can work at the top of their games even as they grow and broaden their skills, increases the productivity and creativity of the organization’s output through high levels of collaboration, and therefore drives the best performance on a sustained basis.  This doesn’t have to be Return Path’s culture or mean that you have to live by our values.  This could be your culture and your values.  You just have to believe that those things drive your success.

Not a believer yet?  Last year, we had voluntary turnover of less than 1%.  We promoted or gave new assignments to 15% of our employees.  And almost 50% of our new hires were referred by existing employees.  Those are some very, very healthy employee metrics that lead directly to competitive advantage.  As does our really exciting announcement last week of being #11 in the mid-sized company on Fortune Magazine’s list of the best companies to work for.

Book Short:  On The Same Page

Being on the same page with your team, or your whole company for that matter, is a key to success in business.  The Four Obsessions of an Extraordinary Executive, by Patrick Lencioni, espouses this notion and boils down the role of the CEO to four points:

1. Build and maintain a cohesive leadership team
2. Create organizational clarity
3. Overcommunicate organizational clarity
4. Reinforce organizational clarity through human systems

Those four points sound as boring as bread, but the book is anything but.  The book’s style is easy and breezy — business fiction.  One of the most poignant moments for me was when the book’s “other CEO” (the one that doesn’t “get it”) reflects that he “didn’t go into business to referee executive team meetings and delivery employee orientation…he loved strategy and competition.”  Being a CEO is a dynamic job that changes tremendously as the organization grows.  This book is a great handbook for anyone transitioning out of the startup phase, or for anyone managing a larger organization.

I haven’t read the author’s other books (this is one in a series), but I will soon!

My name is Matt Blumberg. I am a technology entrepreneur and business builder based in New York City. I am CEO of Markup AI, the leading provider of Content Guardian Agents to companies of all sizes looking to scale their use of AI to generate content smartly and safely. We are defining a new category in the Generative AI space and crushing it.

Before that, I started a company called Bolster, which was an on-demand executive talent marketplace.  We created a new way to scale executive teams and boards aimed at early and mid-stage tech companies. The business sort of worked and sort of didn’t work. We wound it down in 2025 and decided to focus on helping the portfolio companies we invested in via Bolster Ventures and help our friends with talent referrals on a more informal basis.

My longest career stint was Return Path, a company I started in 1999, which we sold in 2019.   We created a business that was the global market leader in email intelligence, analyzing more data about email than anyone else in the world and producing applications that solve real business problems for end users, commercial senders, and mailbox providers.  In the end, we served over 4,000 clients with about 450 employees and 12 offices in 7 countries.  We also built a wonderful company with a signature People First Culture that won a number of awards over the years, including Fortune Magazine’s #2 best mid-sized place to work in 2012.

Early in my career, I ran marketing and online services for MovieFone/777-FILM (www.moviefone.com), now a division of AOL. Before that — I was in venture capital at General Atlantic Partners (www.gapartners.com), and before that, a consultant at Mercer Management Consulting (www.mercermc.com). And I went to Princeton before that.

Based on this blog, I wrote a book called Startup CEO:  A Field Guide to Scaling Up Your Business, which was published by Wiley in 2013 and updated in 2020. I followed that by co-authoring a book with a number of my fellow executives from Retutrn Path and Bolster called Startup CXO: A Field Guide to Scaling Up Your Company’s Critical Functions and Teams; as well as the second edition of Startup Boards: A Field Guide to Building and Leading an Effective Board of Directors along with Brad Feld and Mahendra Ramsinghani. I hosted a podcast called The Daily Bolster, with over 200 micro-episodes (mostly 5-6 minutes long) where I interview other CEOs to share their stories and hacks.

I have been married for over 25 years to Mariquita, who is, as I tell her all the time, one of the all-time great wives. We have three great kids now in their late teens, Casey, Wilson, and Elyse.

I have lots of other hobbies and interests, like coaching my kids’ baseball and softball teams; traveling and seeing different corners of the world; reading all sorts of books, particularly about business, American Presidential history, art & architecture, natural sciences (for laymen!), and anything funny; cooking and wishing I lived in a place where I could grill and eat outdoors year-round; playing golf; lumbering my way through the very occasional marathon, eating cheap Mexican food; introducing my kids to classic movies; and playing around with new technology. I hosted a limited edition podcast series called Country Over Self which explored the topic of virtue in the Oval Office along with a dozen prominent presidential historians.

IF YOU WANT TO UNDERSTAND WHAT THIS BLOG IS ALL ABOUT, read my first two postings: You’re Only a First Time CEO Once, and Oh, and About That Picture, as well as my updated post when I relaunched the blog with its new name, StartupCEO.com.

5 Ways to Get Your Staff on the Same Page

[This post first appeared as an article in Entrepreneur Magazine as part of a new series I’m publishing there in conjunction with my book, Startup CEO:  A Field Guide to Scaling Up Your Business]

When a major issue arises, is everybody at your company serving the same interests? Or is one person serving the engineering team, another person serving the sales team, one board member serving the VC fund, another serving the early-stage “angels” and another serving the CEO? If that’s the case, then your team is misaligned. No individual department’s interests are as important as the company’s.

To align everyone behind your company’s interests, you must first define and communicate those goals and needs. This requires five steps:

1. Define the mission. Be clear to everyone about where you’re going and how you’re going to get there (in keeping with your values).
2. Set annual priorities, goals, and targets. Turn the broader mission into something more concrete with prioritized goals and unambiguous success metrics.
3. Encourage bottom-up planning. You and your executive team need to set the major strategic goals for the company, but team members should design their own path to contribution. Just be sure that you or their managers check in with them to assure that they remain in synch with the company’s goals.
4. Facilitate the transparent flow of information and rigorous debate. To help people calibrate the success, or insufficiency, of their efforts, be transparent about how the organization is doing along the way. Your organization will make better decisions when everyone has what they need to have frank conversations and then make well-informed decisions.
5. Ensure that compensation supports alignment (or at least doesn’t fight it). As selfless as you want your employees to be, they’ll always prioritize their interests over the company’s. If those interests are aligned – especially when it comes to compensation – this reality of human nature simply won’t be a problem.

Taken in sequence, these steps are the formula for alignment. But if I had to single out one as the most important, it would be number 5: aligning individual incentives with companywide goals.

It’s always great to hear people say that they’d do their jobs even if they weren’t paid to, but the reality of post-lottery-jackpot job retention rates suggests otherwise. You, and every member of your team, “work” for pay. Whatever the details of your compensation plan, it’s crucial that it aligns your entire team behind the company’s best interests.

Don’t reward marketers for hitting marketing milestones while rewarding engineers to hit product milestones and back office personnel to keep the infrastructure humming. Reward everybody when the company hits its milestones.

The results of this system can be extraordinary:

• Department goals are in alignment with overall company goals. “Hitting product goals” shouldn’t matter unless those goals serve the overall health of your company. When every member of your executive team – including your CTO – is rewarded for the latter, it’s much easier to set goals as a company. There are no competing priorities: the only priority is serving the annual goals.
• Individual success metrics are in alignment with overall company success metrics. The one place where all companies probably have alignment between corporate and departmental goals is in sales. The success metrics that your sales team uses can’t be that far off from your overall goals for the company. With a unified incentive plan, you can bring every department into the same degree of alignment. Imagine your general counsel asking for less extraneous legal review in order to cut costs
• Resource allocation serves the company, rather than individual silos. If a department with its own compensation plan hits its (unique) metrics early, members of that team have no incentive to pitch in elsewhere; their bonuses are secure. But if everyone’s incentive depends on the entire company’s performance, get ready to watch product leads offering to share developers, unprompted.

This approach can only be taken so far: I can’t imagine an incentive system that doesn’t reward salespeople for individual performance. And while everyone benefits when things go well, if your company misses its goals, nobody should have occasion to celebrate. Everybody gets dinged if the company doesn’t meet its goals, no matter how well they or their departments performed. It’s a tough pill to swallow, but it also important preventive medicine.

We have a little more than two weeks of The Daily Bolster podcast under our belts now, and we’re off to a great start! I announced it here, and I thought I’d post links to the first bunch of episodes…I don’t think I’ll do this regularly, though. You can listen to all episodes here (or on your favorite podcast platform), and never miss an episode when you sign up for daily email notifications.

Episode 1: 3 Tips to Scale Your Culture with Nick Mehta

Our very first guest on The Daily Bolster was Nick Mehta, CEO of Gainsight. As an early-stage startup or a small business, you have significant influence over the culture—but what happens when you’re one of many? Nick and I discussed what happens to company culture when you achieve your scaling and growth goals.

Episode 2: Managing Up with Cristina Miller

Executives are often caught in the middle of the leadership dynamic, managing both up and down the organization. Cristina Miller—a seasoned, results-driven executive and board member (including on Bolster’s board!) with a strong track record—shared what it looks like to set expectations and build a strong relationship with your CEO.

Episode 3: Common Mistakes Founders Make with Fred Wilson

Fred Wilson has been a venture capitalist since 1987 and has worked with me for over 20 years now—so it’s fair to say he’s witnessed a few founders and become familiar with their most common mistakes. Listen to this episode to learn how to recognize and avoid those mistakes for yourself.

Episode 4: Cultivating Talent to Promote Internally with Nick Francis

In this episode, Nick Francis—co-founder and CEO of Help Scout—joins me to discuss what it takes to cultivate in-house talent and embody organizational values. I talk about my playbook for building effective teams and developing leaders with a growth mentality as part of this.

Episode 5: Deep Dive with Jeff Epstein

Career shifts are more common now than ever, even for senior executives. Experienced CFO and operator (and one of my former board members) Jeff Epstein joined me for an extended episode about the ins and outs of career transitions and the surprises that come with them, from role changes to new industries to vastly different organizational structures. Tune in to follow the shifts in Jeff’s career journey, hear about the lessons he learned firsthand, and get his advice for founders looking to scale. “I always wanted to develop a circle of competence and then over time expand the circle,” Jeff says. “You just learn more.”

Episode 6: Hallmarks of Successful Founders with David Cohen

David Cohen, Founder and Chairman at Techstars, shares the top three signs he looks for that differentiate successful founders—things that are nearly impossible to fake. Either you have them, or you don’t. This one is awesome.

Episode 7: Success as a Fractional Exec with Courtney Graeber

If you know anything about Bolster, you know we’re a champion for fractional executives. As an Interim Chief People Officer, HR Executive Consultant, and trusted mentor to executive teams, Courtney Graeber provides feedback and recommendations that enhance organizational culture and attract, develop, and retain top talent. Many of her clients are navigating transitional periods—and that’s where Courtney’s expertise comes in. Listen in to learn what it’s like to be (or work with) a fractional head of people.

Episode 8: 3 Ways VCs Say “No” Without Saying “No” with Jenny Fielding

It’s important for founders to be able to hear what’s left unsaid in conversations with VCs. Sometimes, says one of NYC’s top pre-seed investors Jenny Fielding, VCs aren’t ready to invest in a startup, but they’re not ready to say no, either.  Here, Jenny shares three signs a VC may be saying “no” without saying the words—and what founders should do next.

Episode 9: Building a Strong Culture with Jailany Thiaw

Jailany Thiaw, founder and CEO of UPskill, a future-of-work startup automating feedback in entry-level hiring pipelines, joins me to discuss the best ways to get company buy-in as you build and maintain a strong and welcoming culture—especially in an early stage or remote environment.

Episode 10: Deep Dive with Brad Feld

Brad Feld is partner and co-founder of Foundry, and a long time early stage investor and entrepreneur who I’ve also worked with for more than two decades. In this episode, he and I take a deep dive into how startups and venture capital have changed over the past 25 years—and what has stayed the same.  They also discuss the dynamics of startup boards, along with common characteristics that make founders or companies successful at scale.

Episode 11: The Value of Podcasting with Lindsay Tjepkema

This episode is all about podcasting. Meta, right? Lindsay Tjepkema is the CEO and co-founder of Casted, the podcasting solution for B2B marketers.  She and I dive into the reasons why podcasts are such a great way to get your voice—literally—out into the world. Tune in to hear Lindsay’s tips for starting a podcast as a CEO, setting expectations, asking meaningful questions, and creating human connection. We’ve loved partnering with Lindsay and her team so far on The Daily Bolster!

Episode 12: Interviewing for “Culture Fit” with Rory Verrett

What does it mean to interview for culture fit? How should CEOs and leaders go about doing it—and is there a better way? Rory Verrett is the founder and managing partner of Protégé Search, the leading retained search and leadership advisory firm focused on diverse talent, and is also on Bolster’s Board of Directors. He and I discuss why CEOs are not always the best arbiters of company culture, then we dive into what it means to look for specific values throughout the interview process, rather than the vague concept of a culture fit.

The Daily Bolster is for people in the startup world want to hear from industry experts of all backgrounds, but don’t always have the time to listen to full length interviews, even at 2x speed. Instead, we’re getting straight to the point with mostly 5-minute episodes. Any and all feedback welcome!