(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.

A New (Old) Favorite Returns as a Blog

Andy Sernovitz’s very cleverly-named Damn, I Wish I’d Thought of That is back, this time in blog and RSS feed format as well as, of course, email newsletter format.  Andy is a Return Path alum and does a great job of crystallizing smart and clever ideas for marketers into manageable nuggets, particularly around viral and word-of-mouth marketing (Andy wrote a great book on WOM marketing, which I reviewed here).

He was nice enough to interview me for his blog.  As a teaser, Andy asked me (and a bunch of other people) three questions:

Great marketing comes down to one simple idea: Earn the respect and recommendation of your customers, and they will do the rest. What is your advice for any company that wants to …

1 … make people happy?

2 … earn respect?

3 … get a word of mouth recommendation?

The full interview is on Andy’s new site here.

Counter Cliche:  Connected at the Top

Fred hasn’t written an official VC Cliche of the Week for a while, but his post yesterday on Connectors is close enough — in it, he talks about how he likes to be a good Connector between people and thinks it’s a quality of great VCs.

First, we should give credit to Malcolm Gladwell for a great definition of Connectors in The Tipping Point.  Gladwell not only defines Connectors as Fred has but also defines two other types of people who are critical in the social networking/buzz building arena:  Mavens and Salesmen.  I’d argue that a great VC has to have a bit of all three!

But in terms of entrepreneurs (the point of the counter cliche series), is being a Connector a prerequisite for success?  I think the answer is nuanced, but it’s probably no.  I’ve met great CEOs who are fairly introverted and whose brains don’t work in the Connector kind of way.  And they can be great at developing product, even running operations.  But if you’re an entrepreneur and not a Connector, you’d better have one or more of them on your management team (think sales or business development or marketing) to make up for that missing piece of the equation to make sure your company is connecting the dots outside the corporate walls.  Otherwise, you’re sure to miss out on opportunities.

The one area where I would say that being a Connector is critical for an entrepreneur is internally within the company.  If you’re going to lead the troops effectively, you do need to be able to make Connections between people within the company, especially as the business grows.  And off-topic a bit (literally if not figuratively), you also need to be able to connect with your staff members on a personal level and make sure that people are connected to the company and its mission.  I’m not sure these are things that an entrepreneur can delegate as long as he or she is CEO.

Sometimes You Just Need a 2×4 Between the Eyes

Freshman year in college, fall semester, my friend Peggy and I were in a small seminar class together on Dante. We thought we were pretty smart before the class started. And that we were great writers. Lots of As in high school. Then we wrote our first paper. Professor Bob Hollander gave me a C-. I think Peggy got a D. We were devastated. And pissed. Sure, the ensuing cocktail took the edge off (this was college, after all), but we both scheduled time with the professor during his office hours to figure out where our carefully honed academic trains had gone off the tracks.

Essentially what he said to each of us was this (you have to picture the 60-something professor in a turtleneck smoking a pipe with gravely voice for full effect): “Matthew, your writing wasn’t the worst I’ve ever seen. But I feel like you can do better, and sometimes you just need a 2×4 between the eyes.” End of meeting. Thank you, sir, may I please have another?

I couldn’t have been more irritated. But I will tell you one thing. I worked four times as hard on my next paper, got an A-, and elevated my game permanently. Not just for this one class, but for all of them. Bob was right. His 2×4 between my eyes worked.

Sometimes when we deliver performance feedback in business, this approach makes sense. There are times when someone is really doing poorly and needs harsh (fair, but honest) feedback. There are also times when someone is doing so-so but generally just not living up to his or her promise and should be doing better. And in those cases, you have to just make a judgment call about whether to give feedback on the margin or go for the full 2×4 to drive the point home and get someone to really elevate his or her game for good.

What Gets Said vs. What Gets Heard

I’ve been on the edge of a few different situations lately at work where what seems like a very clear (even by objective standards) conversation ends up with two very different understandings down the road.  This is the problem I’d characterize as “What gets said isn’t necessarily what gets heard.”  More often than not, this is around delivering bad news, but there are other use cases as well.  Imagine these three fictitious examples:

• Edward was surprised he got fired, even though his manager said he gave him repeated warnings and performance feedback
• Jacob thought his assignment was to write a proposal and get it out the door before a deadline, but his manager thought the assignment was to schedule a brainstorming meeting with all internal stakeholders to get everyone on the same page before finalizing the proposal
• Bella gets an interim promotion – she still needs to prove herself for 90 days in the new job before the promotion is permanent and there is a comp adjustment – then gets upset when the “email to all” mentions that she is “acting”

Why does this happen?  There are probably two main causes, each with a solution or two.  The first is that What Gets Said isn’t 100% crystal clear.  Delivering difficult news is hard and not for the squeamish.  What can be done about it?  The first problem — the crystal clear one — can be fixed by brute force.  If you are giving someone their last warning before firing him, don’t mumble something about “not great performance” and “consequences.”  Look him in the eye and say “If you do not do x, y, and z in the next 30 days, you will be fired.” 

The second cause is that, even if the conversation is objectively clear, the person on the receiving end of the conversation may WANT to hear something else or believes something else, so that’s what “sticks” out of the conversation.  Solving this problem is more challenging.  Approaching it with a lengthy conversation process like the Action Design model or the Difficult Conversations model is one way; but we don’t always have the time to prepare for or engage in that level of conversation, and it’s not always appropriate.  I’d offer two shortcut tips to get around this issue.  First, ask the person to whom you’re speaking to “play back in your own words what you just heard.”  See it she gets it right.  Second, send a very clear follow-up email after the conversation recapping it and asking for email confirmation.

People are only human (for the most part, in my experience), and even when delivering good news or assignments, sometimes things get lost in translation.  But clarity of message, boldness of approach, and forcing playback and confirmation are a few ways to close the gap between What Gets Said and What Gets Heard.

Closure

This past weekend was a weekend of closure for me. As I prepare to leave the city after almost 17 years and the apartment I’ve lived in for almost 15, we had my two original roommates from this apartment in town for the weekend with their families for a bit of a farewell party. Times certainly have changed – from three single guys to three families and 7, almost 8 kids between us. Sitting around and noting that all three couples had either gotten engaged or first started dating within the confines of Apartment 35B, then saying goodbye as everyone left the apartment for the last time, was a little surreal. But overall, having everyone around was great fun and was a fitting way to mark the occasion.

If that wasn’t enough to drive the point home, we were lucky enough to get tickets to the Yankees game last night, which was the last home game the Yanks will play in their 85-year old stadium before moving across the street next season to their fancy new home. The ceremony before the game, which featured a bunch of prominent Yankee greats and their progeny (Babe Ruth’s daughter threw out the opening pitch!), was similarly surreal, but a fitting ending to a long-standing tradition.

Why is closure important? I’m not a psychologist, but for me and my brain anyway, celebrating or formally noting the END of something helps move on to the BEGINNING of the next thing. It helps compartmentalize and define an experience. It provides time to reflect on a change and WHY it’s (inevitably) both good and bad. And I suppose it appeals to the sentimentalist in me.

I think it’s important to create these moments in business as well as in one’s personal life. We and I have done them sporadically at Return Path over the years. Moving offices as we expand. Post-mortems on projects gone well or badly. Retrospectives with employees who didn’t work out, sometimes months after the fact. Whether the moment is an event, a speech at an all-hands meeting, or even just an email to ALL, one of the main jobs of a leader in building and driving a corporate culture is to identify them and mark them.

(Post 4 of 4 in the series on Scaling CBDO’s- other posts are, When to hire your first Chief Business Development Officer, What does Great look like in a Chief Business Development Officer and Signs your Chief Business Development Officer isn’t Scaling)

Other than the weekly executive meeting, your day as a CEO rarely has an entry of “meet the CBDO.” Because of the infrequency of deals it’s critical to engage with the CBDO with a regular cadence so that when something does come up you’re not getting to know each other again. Anyway, a few ways I’ve typically spent the most time or gotten the most value out of CBDOs over the years are:

One way to engage with the CBDO is to make ecosystem maps together. It’s important for you and the CBDO to understand exactly what ocean you’re swimming in, which other fish are swimming nearby, and which ones are sharks you need to watch out for. This understanding is what can make or break the CBDO role and it is vital that you, as CEO, engage with and help shape that understanding since you’ll have specialized knowledge of some of the other players, their CEOs, and their strategies. The ecosystem map is actually a fun thing to create and not only does it lead to better clarity about where you’re at and where you could go, it also aligns you and the CBDO on a deeper, strategic level.

While you can plan out the ecosystem mapping activity, a lot of the engagement I have with the CBDO is sporadic, unplanned, and spontaneous.  The deal world is intense and unpredictable.  When you’re working on a deal you may be talking to your CBDO 20 hours a day.  When it’s business as usual, you may go weeks without deep interaction. So unlike the other executives, the time you engage with your CBDO will be compressed into highly intense time frames.

A third way I engage with the CBDO is in-market and in-transit.  As with the CRO, I spend time extensively with the CBDO since we are likely going to the same place at the same time a few times a year.  Since the essence of the job as a CBDO is to be a trusted ambassador on all fronts, as Ken identified correctly in his section of Startup CXO, the CEO has to constantly be engaging the ambassador on the organization’s most current thinking, positioning, forward-looking strategy.  Over the life of Return Path (and currently at Bolster), there’s no question that I spent the majority of my “planes, trains, and automobiles work time” with Ken.

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

The Best Place to Work, Part 4: Be the Consummate Host

Besides Surrounding yourself with the best and brightest , Creating an environment of trust,  and Managing yourself very, very well, it’s important for you as a creator of The Best Place to Work to Be the Consummate Host.

What does that mean?  This is how I approach my job every day.  I think of the company as a party, where I’m the host.  I want everyone to have a good time.  To get along with the other guests.  To be excited to come back the next time I have a party (e.g., every day).

By the way, I always have co-hosts, as well – anyone who manages anyone in the company.  If I can’t do something specific below, someone on my executive team does it.  Sometimes, two of us do it!  Examples include:

• I interview people like I’m a bouncer at an exclusive club.  We do very personal new employee orientations.  We do personal check-ins after 30 and 90 days to make sure new employees are on track
• I attend every company function that I can and work the room as a host, even if it’s not “my” event – sometimes it means sacrificing long conversations and conversations with friends for smaller ones and meeting new people
• I call every employee (voicemail ok) and write a note and/or send a gift every anniversary of their employment with the company
• I write notes to people when they do something great or get a promotion

Full series of posts here.

Half Your Waking Hours

I just came back from our annual Board/Management ski trip (and Board meeting) — we had about half of both groups join, which is typical given the time commitment.  We had a great time, and the conversation for the three days was a nice blend of business and personal. 

The thing that struck me during the weekend — and I am reminded of this regularly in the office and at other work events as well — is how much I genuinely enjoy the company of the people with whom I work.  Whether it’s my senior staff, my Board, or anyone I can think of in other roles within Return Path, we can manage to have a good time together and have fun as well as be productively thinking about and discussing work.

With generic assumptions of 8 hours of sleep a night and 8 hours of work a day (neither one being true of course, but canceling each other somewhat out here), we spend half our waking hours on the job.  So we might as well choose to work with people that we get along with!  That doesn’t mean everyone we hire at Return Path has to be like-minded or have the same sense of humor.  But it does mean that we look for people who have that spark in their eye that says "I get it"; it means we want to find people who are articulate and have strong convictions and are not afraid to speak their mind; and it means we screen for people who can be light-hearted and don’t take themselves too too too seriously when we recruit, interview, and hire.

Think about that "half your waking hours" thing the next time you’re hiring someone.  Which candidate (of the technically qualified ones who are in the right zone in terms of compensation) would you rather spend your day with?  In my former career in management consulting, we used to call this the "Cleveland Airport test" — as in, if you were stuck in the Cleveland Airport with this candidate, would you be happy or sad about it?

Email Marketing Good and Bad:  Case Study Snippets

I had a good meeting this morning with one of our long-time multi-channel retailer clients who is in town for Shop.org’s Annual Summit.  Over the course of our conversation, she relayed two things going on in her world of email marketing at the moment that bear repeating (with her permission, of course).

First, the good.  In a recent study, our retailer hero determined that customers who receive their email newsletters and offers (not even open/click, just receive) spend on average 3x as much on in-store purchases than their non-email counterparts in any given week or for any given campaign.  Talk about deriving non-email or non-click value from your email marketing efforts!

Second, the bad (ok, well, it’s the ugly as well).  Our retailer hero was just nailed by Spamhaus because someone out there complained about a transactional email he or she received from the retailer.  She estimates that the poor Spamhaus listing is costing her millions of dollars a year in lost sales from regular customers.  The email was literally about a refund that the retailer owed the customer (why there was a complaint — who knows?).  What did Spamhaus suggest the retailer do?  Repermission their list around transactional messages — “or else.”  Seems to me that that’s a pretty tough stance to take on rather shaky evidence and with no appropriate dispute resolution mechanism (e.g., one that’s not just tuned to mailers’ interests, but one that’s fair in the broadest sense of the word).  No wonder Spamhaus is being sued, and no wonder the vigilante blacklist providers of the world are losing traction with ISPs and corporate system administrators.  Authentication and real, professionally run reputation systems with ample amounts of representative data, feedback loops, and dispute resolution mechanisms will ultimately win the day over the vigilantes of the world.  Folks like Spamhaus can get things right lots of the time and in fact do provide a valuable cog in the global world of spam fighting, but they’re less great at making amends when they don’t.

So email continues to have its challenges around filtering and deliverability…but how cool is it that marketers are really sinking their teeth into metrics that prove how effective the email channel is for driving sales, both online and offline?

Like Fingernails on a Chalkboard

Anyone who worked in the Internet in the early days probably remembers all-too-vividly how silly things got near the end.  Even those who had nothing to do with the industry but who were alive at the time with an extra dollar or two to invest in the stock market probably has some conception of the massive roller coaster companies were on in those years.

The memories/images/perceptions all come crashing down in the latest chapter of Tom Evslin’s blook hackoff.com in a manner that reminds me of the sound of fingernails racing down a chalkboard.  You’ve heard it before, you can’t forget it, you squirm every time you hear it, but you can’t tear yourself away from it.

I think Chapter 9, Episode 6 and Episode 7 lay out every single stereotype of the Internet’s bad old days in two easy tales:

– The CEO who says “The main reason for this meeting is to figure out how to get the stock price up again”

– The blaming of the investment bankers for the bad business model

– The head of sales who doesn’t understand his vanishing pipeline and the CEO who turns a blind eye, sacrificing future sales to make the current quarter’s numbers

– The surprisingly shocking realization that adding 30 new people per quarter costs a lot of money

– The parade of the lawsuits, lawyers, and insurance policies

– The notion that all problems can be solved with a new product, which of course must be built immediately, but with a smaller engineering team

– The struggle about laying off staff and the comment that “you can’t cut your way to growth and greatness”

If you’ve haven’t tried the blook yet, you can start at the beginning with the daily episodes, on the web or by RSS, or you can download chapters in pdf format on the site.  It’s a great piece of daily brain candy.