First in my series of posts around creating the best place to work  is to Surround yourself with the best and brightest.  This one is simple.  Build the best team you can possibly build…as you need it.

As a founder, you may be the best person at doing everything in your company, especially if you are a technical founder.  But as my long-time Board member at Return Path Greg Sands always says, when the organism grows, cells start to specialize.  Eventually, you need a liver and a brain.  Just like companies need a head of sales and a CFO (not to imply that Anita likes the occasional cocktail or that Jack likes math – turns out both like both).

How does this come into play as a CEO?

-Don’t be afraid to hire people better than you at their specialty – older, wiser, more experienced, more expensive

– Check references carefully – don’t get suckered in by resume or rolodex – some successful big company people don’t actually know how to do work or build a business, so you have to dig and find back-channel references

– Don’t overhire before you’re ready, but especially as a start-up, better to hire 3 months before you need the position, not 6 months too late

-Remember that you are the CEO.  Even if you hire very experienced people in specific roles, you have the best global view of everything going on in the company.  And you need to pay attention to people on your team and actively manage them, even experts who are older or wiser than you are

Surrounding yourself with the best and brightest can be daunting and even threatening to some CEOs.  But you have to do it to grow your business.  And you have to keep doing it as you keep growing your business (and your staff has to do the same!).

More Good Inc.

Last year I was pleased and proud to write about our debut on the Inc. 500 list of America’s fastest growing companies.  At that time I wrote that “Now our challenge, of course, is STAYING on the list, and hopefully upping our ranking next year!”  Well, I am again please and proud to announce that we, in fact, stayed on the list.  (You can read all the Inc. coverage here and see our press release about the ranking here.)

Unfortunately, we didn’t make the second part of our goal to up our rank.  But, we did up our growth – our three-year revenue growth rate was 18% higher than last year.  This is a testament to the hard work of our team (now 150 strong!) and wouldn’t be possible without the support of our many great clients (now 1,500 strong!).  Most importantly, we see no end in sight.  In fact, 2008 promises to be an even bigger year for us as we poise for continued growth.  By the way, would you like to be part of a team that has now ranked as one of America’s fastest growing companies two years in a row?  Check out our Careers page and join the team that is advancing email marketing, one company at a time.

(This post also appeared on Bolster.com and builds on last week’s post where I introduced my new startup, Bolster)

Welcome to Bolster, the on-demand executive talent marketplace. We are creating a platform that is the new way to scale an executive team and board.

We believe that startups and scaleups are not average companies. Their rapid growth means their appetite for talent constantly outstrips their budget — and that they can’t spend months searching for it. Their dynamic industries dictate that they keep pace with bigger and better funded competitors. Their leadership teams — the people and the roles — are always changing. Their CEOs spend a ton of time hiring and coaching their leaders and shaping the complexion and direction of the team. They stress out about big expensive new executive hires when sometimes they just need to level-up an existing manager or “try before they buy.” Their Boards frequently jump in to help, but those efforts can be a little ad hoc and inefficient.

We believe that experienced executives working as consultants is the wave of the future. The number of career executives who work flexibly and on-demand for a living is skyrocketing in recent years. People are more often “between things” and are interested in plugging into shorter-term engagements while continuing to look for their next full-time role. People are retiring younger, yet wanting to keep contributing. And even fully-employed execs like to advise companies and serve on Boards. Whether these people are career consultants or are looking for a “side hustle” or just to pay something forward to a future generation of leaders, they all have two common problems: finding work is time consuming and they’re often not good at or don’t like doing it; and managing their back office, everything from insurance to legal to tax to marketing, is a drain on time that could otherwise be spent with clients or family.

We believe that a new kind of talent marketplace is needed to meet the unique and complex requirements of both audiences — the freelance, or flexible, seasoned executive, and the startup or scaleup CEO who thinks holistically about his or her leadership team and carefully tends them like a garden. We are building a platform to make instant, tailored, vetted matches between talent and companies without the randomness of a job board and without the theater, long lead times, and cost, of a full service agency 

Service marketplaces like ours work best when they help their stakeholders solve other meaningful, related problems.In this case, we believe that the need for back office services will help executive consultants focus on more important things. And we believe that CEOs need lightweight and dynamic support in thinking through the composition and skills required of their executive teams both today and 6-18 months in the future.

That is the essence of the business we are building. A business to quickly match awesome companies with awesome freelance executives and to help both sides be better at what they do. We are here to make it easier for you to:

• Bolster your executive team. For our Clients, our pledge to you is that we will quickly and cost-effectively fill the gaps in your leadership ranks (whether interim, fractional, advisory, board, or project-based) with trusted, curated talent, and that we will give you a platform to evaluate your overall leadership team and help you think through your future needs as your company evolves. Think of us as a shortcut to scaling your leadership team.
  
• Bolster your board. The best boards are the ones with multiple independent directors who come from diverse backgrounds with diverse points of view. We also pledge to our Clients that we will find great matches to help fill out their boardrooms as their strategic advisory needs change over time.
  
• Bolster your work. For our Members, our pledge to you is that we will find you the right kind of interesting clients and help you manage your back office so you can focus on your work (and all the other important things in your life!).
  
• Bolster your portfolio. For our Portfolio Partners, VC and PE board members, our pledge to you is that we will make it easier for you and your firm to both drive successful on-demand executive placements for your portfolio company CEOs, and to manage and expand your firm’s network of flexible executive talent. 

We are an experienced team of entrepreneurs and operators who have scaled multiple businesses throughout our careers. All of us worked together as part of the leadership team at Return Path, a leading email technology company that we scaled from 0 to $100mm in revenue and 500 employees in 12 locations around the world while winning numerous Employer of Choice awards. All of us have independent experience scaling other businesses, small and large, public and private. All of us have experience being on-demand executives as well — whether interim, fractional, advisory, project-based, or board roles, we know the landscape of both our members and our clients. 

We’ve all dealt with the stress of having product-market fit and market opportunities but not being able to capitalize on those opportunities because we were missing key talent. And we’ve tried everything from executive search firms (expensive, time-consuming, and slow), to leveling up people (will they be able to grow into the role?), to leaning in to our board (hit or miss, inefficient). Heck, we’ve been desperate enough to follow up on the “my cousin’s boyfriend has an uncle, and he might know someone” lead.

We believe there is a better way for startups and scaleups to find executive talent. Along the way, I published a book about scaling startups called Startup CEO: A Field Guide to Scaling Up Your Business that has sold over 40,000 copies to CEOs around the world. And our whole team is working on a new book called Startup CXO: A Field Guide to Scaling Up Your Teams, which is coming out in early 2021. Our team has a maniacal focus on helping startup teams scale and flourish and on helping leaders develop into the best version of themselves. That’s what we’re all about. 
Plus, we have an amazing group of investors behind us who know how to grow businesses like ours and have incredible reach into the startup and scaleup world. More about that later. For now, we are excited to soft launch Bolster and begin unleashing the power of on-demand executive talent to our Clients. Thank you for being on this journey with us. If you’re interested in the somewhat unusual story of how the company was founded, it’s here.

My cofounder Cathy wrote a great post on the Bolster blog back in January called Procrastinating Executive Development, in which she talks about the fact that even executives who appreciate the value of professional development usually don’t get to it because they’re too busy or don’t realize how important it is. I see this every day with CEOs and founders. Cathy had a well phrased but somewhat gentle ask at the end of her post:

My ask for all CEOs is this: give each of your executives the gift of feedback now, and hold each other accountable for continued growth and development to match the growth and development of your company.

Let me put it in starker terms:

Grow or Die.

Every executive, every professional, can scale further than they think is possible, and further than you think is possible. Most of us do have some ceiling somewhere…but it will take us years to find it (if we ever find it). The key to scaling is a growth mentality. You have to not just value development, you have to crave it, view it as essential, and prioritize it.

Startups are incredibly dynamic. You’re creating something out of nothing. Disrupting an industry. Revolutionizing something. Putting a dent in the universe. For a startup to succeed, it has to constantly put something in market, learn, calibrate, accelerate, maybe pivot, and most of all grow. How can a leader of a startup scale from one stage of life to the next without focusing on personal growth and development if the job changes from one quarter to the next?

I was lucky enough to have a great leadership team at my prior company, Return Path, over the course of 20 years. Within that long block of time with many executives, there was a particular period of time, roughly 2004-2012, that I jokingly refer to as the “golden age.” That’s when we grew the business from roughly $5mm in revenue to $50 or $60mm. The remarkable thing was that we executed that growth with the same group of 5-6 senior executives. A couple new people joined the team, and we struggled to get one executive role right, but by and large one core group took us from small to mid-sized. Why? We looked at each other — literally, in one meeting where we were talking about professional development — and said, “we have to commit to individual coaching, to team coaching, and to growth as leaders, or the company will outpace us and we’ll be roadkill.”

That set us on a path to focus on our own growth and development as leaders. We were constantly reading and sharing relevant articles, blog posts, and books. We engaged in a lot of coaching and development instruments like MBTI, TKI, and DISC. We learned the value of retrospectives, transparent 360s, and a steady diet of feedback. We challenged ourselves to do better. We worked at it. As one of the members of the Golden Age said of our work, “we went to the gym.”

The “Grow or Die” mantra is real. You can’t possibly be successful in today’s world if you’re not learning, if you don’t have a growth mentality. You are never the smartest person in the room. The minute you are convinced that you are…you’re screwed.

If you don’t believe me, look at the development of your business itself as a metaphor for your own development as a leader. What happens to your startup if it stops growing?

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

How to Wow Your Employees

Here at Return Path we like to promote a culture of WOW and a culture of hospitality.  Some of you may be asking, Why Wow your employees?   The answer is, there is nothing more inspirational than showing an employee that you care about him or her as an individual.  The impact a WOW has is tremendous.  Being a manger is like being in a fishbowl.  Everything you do is scrutinized by your team.  You lead by example whether you want to or not and showing your own vulnerability/humanity has an amazing bonding effect.

Why do you want to foster Wow moments with your team?  High performing teams have a lot of Wow going on.  If all members of a team see Wow regularly, they are all inspired to do more sooner and better.

Here are 15 ways to Wow your employees

1. Take them or her to lunch/breakfast/drinks/dinner quarterly individually, one nice one per year
2. Learn their hobbies and special interests; when you have a spiff to give, give one that is in line with these
3. Remember the names of their spouse/significant other/kids/pets
4. Share your development plan with them and ask for input against it at least quarterly
5. Respond to every email from your staff by the end of the day; sooner if you are on the TO line
6. Ask them what they think of a piece of work you’re doing
7. Ask them what they think of the direction the company is going, or a specific project
8. Periodically take something off each one’s plate, even if it’s clearly theirs to do
9. Periodically tell them to take a day off to recharge, ideally around something important in their lives
10. End every meaningful interaction by asking how they are doing and feeling about work
11. End every interaction by asking what you can be doing to help them do a better job and advance their career
12. Read all job openings and highlight ones that match their interests for future positions
13. Read the weekly award list and call out those FROM and TO your team in staff meetings
14. Send a handwritten note to their home when you have a moment of appreciation for them
15. (If your employee has a team he/she manages) Ask for input before every skip-level interaction and summarize each one after the fact in an email or in person

I try to have Wow moments regularly with people at all levels in the organization.  Here’s one that sticks with me.  At the Colorado summer party several years ago, I went up to someone who was a few layers down in the organization and said hi to her husband and dog by name.  I had met them before, and I work at remembering these things.  The husband was blown away – I hadn’t talked to him in probably two years.  In front of the employee, he gushed – “this is exactly why my wife loves working here – we are totally committed to being part of the RP family.”

There are as many ways to be a great manager and WOW your employees as there are stars in the sky…hopefully these ideas give you a framework to make these your own!

I wrote a colorfully-named post years ago called Onboarding vs. Waterboarding, which detailed out some of the general principles around onboarding new employees that our companies have used over the years. A few weeks back, one of our clients and fellow CEOs of a Series C Ed:Tech company asked me for tips on onboarding senior executives, and some of what I said varied from or built on that earlier post.

Here are a few of the themes we riffed on:

1. Treat the new hire onboarding like you would a merger integration. Why? Well, because adding a new exec to your company is kind of like…a merger integration. Make a long checklist. Assign each item an owner and participating parties. Have a weekly meeting with all key stakeholders specifically to review the onboarding plan. In other words, don’t just leave it up to you, the new exec, and a Day 1 overview meeting with “business as usual” check-ins. Make it its own thing.
   
2. Take great care to communicate expectations and changes internally when the new exec starts. Any new exec, but especially one in a newly-created or upgraded role, will carry a new role description which by definition changes expectations and responsibilities both of the new exec’s role and of other execs’ roles (and possibly your own role or Level-2 team members’ roles). Make it super clear to the organization both in a meeting and in writing what those changes are. If people used to go to you for X, and now they have to go to New Exec for X, don’t leave that to the guesswork and imagination of your team.
   
3. Get out in front of the fact that your exec team has changed. As I always say, any time you change one person on a team (add or subtract), you have…a new team. Treat a new exec onboarding as such, though this will take time. Team dynamics will change, and you need to drive that process. You also need to make sure any shared language and tools on the team take a beat and include the new person. Did you run a DISC or use Myers-Briggs two years ago with your exec team? Great, do it again with the new team. Did you do a major trust/vulnerability exercise at an exec offsite last year? Better do a new one from scratch. This may sound like extra overhead, but it’s worth it. You don’t want the new person to always feel like the new person who is missing an inside joke. Plus, those kinds of things are always good hygiene for exec teams.
   
4. Begin with the end in mind. On Day 1, your new exec won’t know where the bathroom is, unless you are an all-remote company of course. Your objective is for the new exec to be just as autonomous as all other execs ASAP. So, work backwards from 90 or 180 or some other number of days on the question of autonomy. Build this into your integration checklist and weekly integration check-ins (see above), but note this is also a mental evolution both you and the new exec (and the rest of your exec team and the new person’s direct reports) need to go through. Some areas will be more logical for the new exec to be autonomous on Day 1 or at least Month 1. Some will take longer. Be explicit about defining those things.

Special thanks to my friend Amir for inspiring this post!

Book Short:  Chock Full O Management & Leadership

I just finished The Better People Leader, by Charles Coonradt, which was a very short, good, rich read.  It was a pretty expansive book on management & leadership topics — 100 short pages of material that are probably covered by 1,000 pages in other books.

What separates this book from the pack is the rich examples from non-business life that Coonradt sprinkles throughout the book.  They include the tale of a special ed kid who became a mainstream student within a year because his teacher had the courage to ask his fellow students to treat him normally, and the story of how Korean War POWs died in massive numbers not from physical torture but from negative feedback loops.

The closing quote of the book says it all, from Ronald Reagan:  “A great leader is not necessarily one who does the greatest things. He is the one who gets the people to do the greatest things.”  This book gives you quick tips on how to do just that.

Political versus Corporate Leadership, Part III: The First Debate

Well, there you have it. Both of my first two postings on this subject — Realism vs. Idealism and Admitting Mistakes — came up in last night’s debate.

At one point, in response to Kerry’s attempted criticism of him for expressing two different views on the situation in Iraq, Bush responded that he thought he could — and had to — be simultaneously a realist and an optimist. And a few minutes later, Kerry admitted a mistake and brilliantly turned the tables on Bush by saying something to the effect of “I made a mistake in how I talked about Iraq, and he made a mistake by taking us to war with Iraq — you decide which is worse.”

So each candidate exhibited at least one of the traits of good corporate leadership, but on this front anyway, I think Kerry did a better job last night in turning one of his mistakes into a zinger against his opponent.

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.

I wrote part I of this post in 2011, and I feel even more strongly about it today. I generally keep this blog away from politics (don’t we have enough of that running around?), but periodically, I find some common sense, centrist piece of information worth sharing. In this case, I just read a great and very short book, Six Amendments: How and Why We Should Change the Constitution, by former Supreme Court Justice John Paul Stevens, that, if you care about the polarization and fractiousness going on in our country now, you’d appreciate.

If nothing else, the shattered norms and customs of the last several years should point people to the fact that our Constitution needs some revision. Not a massive structural overhaul, but some changes on the margin to keep it fresh, as we approach its 250th anniversary in the next couple decades.

5 Ways to Spot Trends That Will Make You (and Your Business) More Successful

I’ve recently started writing a column for The Magill Report, the new venture by Ken Magill, previously of Direct magazine and even more previously DMNews. Ken has been covering email for a long time and is one of the smartest journalists I know in this space. My column, which I share with my colleagues Jack Sinclair and George Bilbrey, covers 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. Below is a re-post of this week’s version, which I think my OnlyOnce readers will enjoy.

Last week I published my annual “Unpredictions” for 2011. This tradition grew out of the fact that I hate doing predictions and my marketing team loves them. So we compromise by predicting what won’t happen.

But the truth is that the annual prediction ritual – while trite – is really just trend-spotting. And trend-spotting is an important skill for entrepreneurs. Fortunately it’s a skill that can be acquired, at least it can with enough deliberate practice (another skill I talk about here).

Here are five habits you should consider cultivating if being a better trend spotter is in your career roadmap.

Read voraciously. I read about 50 books every year.  About half of them are business books, and I also mix in a bit of fiction, humor, American history, architecture and urban planning, and evolutionary biology.  I keep up with more than 50 blogs and I read all the trade publications that cover email.  I also read the Wall Street Journal and The Economist regularly.  What you read is a little less important than just reading a lot, and diversely.

Use social media (wisely). Julia Child once said that the key to success in life was having great parents. My advice to you is quite a bit simpler:  make friends with smart people. Facebook, Twitter, LinkedIn and others have given us a window into the world unlike any other. Status updates, tweets, and – maybe most important of all – links shared by your network of friends and colleagues gives you a sense of what people are talking about, thinking about and working on. And you can’t just lurk.  You actually have to be “in” to get something “out.”

Follow the money. Pay attention to where money gets invested and spent. This includes keeping an eye on venture capital, private equity, and the public markets, as well as where clients (mostly IT and marketing departments) are spending their dollars and what kinds of people they are hiring. Money flows toward ideas that people think will succeed. A pattern of investments in particular areas will give you clues to what might be the big ideas over the next five to 10 years.

Get out of the office: I think it’s hugely important for anyone in business, and especially entrepreneurs, to spend time in the world to get fresh perspectives. I’m not sure who coined the phrase, but our head of product management, Mike Mills, frequently refers to the NIHITO principle – Nothing Interesting Happens in the Office.  Now that’s not entirely true – running a company means needing to spend a huge amount of time with people and on people issues, but last year I traveled nearly 160,000 miles around the world meeting with prospect, clients, partners and industry luminaries. You don’t have to be a road warrior to get this one right – you can attend events in your local area, develop a local network of people you can meet with regularly – but you do have to get out there.

Take a break. While you need information to understand trends, you can quickly get overloaded with too much data.  Trend spotting is, in many ways, about pattern recognition. And that is often easier to do when your mind is relaxed.  Ever notice that you have moments of true epiphany in the shower or while running? Give yourself time every week to unplug and let your mind recharge. As Steven Covey says, “sharpen that saw”!