As I mentioned earlier this summer, I’ve been working on a new startup the past few months with a group of long-time colleagues from Return Path.  Today, we are officially launching the new company, which is called Bolster.  The official press release is here.

Here’s the business concept.  Bolster is a talent marketplace, but not just any talent marketplace.  We are building a talent marketplace exclusively for what we call on-demand (or freelance) executives and board members.  We are being really picky about curating awesome senior talent.  And we are targeting the marketplace at the CEOs and HR leaders at venture- and PE-backed startups and scaleups.  We’re not a search firm.  We’re not trying to be Catalant or Upwork.  We’re not a job board. 

To keep both sides of the marketplace engaged with us, we are also building out suites of services for both sides – Members and Clients.  For Members, our services will help them manage their careers as independent consultants.  For Clients, our services will help them assess, benchmark and diversify their leadership teams and boards. 

We have a somewhat interesting founding story, which you can read on our website here.  But the key points are this.  I have 7 co-founders, with whom I have worked for a collective 88 years — Andrea Ponchione, Jack Sinclair, Shawn Nussbaum, Cathy Hawley, Ken Takahashi, Jen Goldman, and Nick Badgett.  We have three engineers with whom we’ve worked for several years who have been on board as contractors so far – Kayce Danna, Chris Paynes, and Chris Shealy.  We have four primary investors, who I’ve also known and worked closely with for a collective 77 years — High Alpha and Scott Dorsey (another veteran of the email marketing business), Silicon Valley Bank and Melody Dippold, Union Square Ventures and Fred Wilson, and Costanoa Ventures and Greg Sands.  Pretty much a Dream Team if there ever was one.

So how did our team and I get from Email Deliverability to Executive Talent Marketplace?  

It’s more straightforward than you’d think.  If you know me or Return Path, you know that our company was obsessed with culture, values, people, and leadership development.  You know that we created a cool workforce development nonprofit, Path Forward, to help moms who have taken a career break to care raise kids get back to work.  You know that I wrote a book for startup CEOs and have spent tons of time over the years mentoring and coaching CEOs.  Our team has a passion for helping develop the startup ecosystem, we have a passion for helping people improve and grow their careers and have a positive impact on others, and we have a passion for helping companies have a broad and diverse talent pipeline, especially at the leadership level.  Put all those things together and voila – you get Bolster!

There will be much more to come about Bolster and related topics in the weeks and months to come.  I’ll cross-post anything I write for the Bolster blog here on OnlyOnce, and maybe occasionally a post from someone else.  We have a few opening posts for Bolster that are probably running there today that I’ll post here over the next couple weeks.

If you’re interested in joining Bolster as an executive member or as a client, please go to www.bolster.com and sign up – the site is officially live as of today (although many aspects of the business are still in development, in beta, or manual).

A New VC Ready to Go!

One of the interesting things about being in business for 13 years (as of last week!) at Return Path is that we have been around longer than two of our Venture Capital funds.  Fortunately for us, Fred led an investment in the company with his new fund, Union Square Ventures, even though his initial investment was via his first fund, Flatiron Partners.  And even though Brad hasn’t invested out of his new fund, Foundry Group, he remains a really active member of our group as a Board Advisory through his Mobius Venture Capital investment.

Although our third and largest VC shareholder, Sutter Hill Ventures, is very much still in business, our Board member Greg Sands just announced today that he has left Sutter and started his own firm, Costanoa Venture Capital, sponsored in part by Sutter.  The firm was able to buy portions of some of Greg’s portfolio companies from Sutter as part of its founding capital commitment, so Return Path is now part of both funds, and Greg, like Fred, will continue to serve as a director for us and manage both firms’ stakes in Return Path.

The descriptions of the firm in Greg’s first blog post are great – and they point to companies like Return Path being in his sweet spot:  cloud-based services solving real world problems for businesses, Applied Big Data, consumer interfaces and distribution strategies for Enterprise companies.

I give Greg a lot of credit for going out on his own with a strong vision, something that’s unusual in the VC world.  We’re proud to be part of his new portfolio, and I’m sure he’ll be incredibly successful.  Like Fred and Brad and their new firms, Greg understands the value of being able to write smaller initial checks and back them up over time, he is a disciplined investor, and he is a fantastic Board member and mentor.

In this Olympic Season, Brad gets the gold medal and possibly world record for longest post with his excellent posting on Participating Preferred securities. Fred gets the silver with his contribution on The Double Dip. Dave Jilk and others share the bronze for their many comments.

I won’t add more to the debate but will try to close it by tying together a few of these postings. Fred and Brad both wrote subsequent postings on the related themes of If It Looks Too Good to Be True, It Probably Is and Fantasy vs. Reality. These comments could easily be applied to my thoughts on VCs being silly about bidding up crazy long shot concepts and committing Venture Fratricide.

And of course, it begs the new media version of the age-old question: if a web service costs $25 million to build and then falls into the ether while investors and management sheepishly turn their backs, does it make any noise?

Pret a Manager

My friend James is the GM of the Pret a Manger (a chain of about 250 “everyday luxury” quick service restaurants in the UK and US) at 36th and 5th in Manhattan.  James recently won the President’s Award at Pret for doing an outstanding job opening up a new restaurant.  As part of my ongoing effort to learn and grow as a manager, I thought it would be interesting to spend a day shadowing James and seeing what his operation and management style looked like for a team of two dozen colleagues in a completely different environment than Return Path.  That day was today.  I’ll try to write up the day as combination of observations and learnings applied to our business.  This will be a much longer post than usual.  The title of this post is not a typo – James is “ready to manage.”

1. Team meeting.  The day started at 6:45 a.m. pre-opening with a “team brief” meeting.  The meeting only included half a dozen colleagues who were on hand for the opening, it was a mix of fun and serious, and it ended with three succinct points to remember for the day.  I haven’t done a daily huddle with my team in years, but we do daily stand-ups all across the company in different teams.  The interesting learning, though, is that James leaves the meeting and writes the three points on a whiteboard downstairs near the staff room.  All staff members who come in after the meeting are expected to read the board and internalize the three points (even though they missed the meeting) and are quizzed on them spontaneously during the day.  Key learning:  missing a meeting doesn’t have to mean missing the content of the meeting.

2. Individual 1:1 meeting.  I saw one of these, and it was a mix of a performance review and a development planning session.  It was a little more one-way in communication than ours are, but it did end up having a bunch of back-and-forth.  James’s approach to management is a lot of informal feedback “in the moment,” so this formal check-in contained no surprises for the employee.  The environment was a little challenging for the meeting, since it was in the restaurant (there’s no closed office, and all meetings are done on-site).  The centerpiece of the meeting was a “Start-Stop-Continue” form.  Key learning:  Start-Stop-Continue is a good succinct check-in format.

3. Importance of values.  There were two forms of this that I saw today.  One was a list of 13 key behaviors with an explanation next to each of specific good and bad examples of the behavior.  The behaviors were very clear and were “escalating,” meaning Team Members were expected to practice the first 5-6 of them, Team Leads the first 7-8, Managers the first 10, Head Office staff the first 12, Executives all 13 (roughly).  The second was this “Pret Recipe,” as posted on the public message board (see picture below).  Note – just like our values at Return Path, it all starts with the employee.  One interesting nugget I got from speaking to a relatively new employee who had just joined at the entry level after being recruited from a prominent fast food chain where he had been a store general manager was “Pret really believes this stuff — no lip service.”

I saw the values in action in two different ways.  The first was on the message board, where each element of the Pret Recipe was broken out with a list of supporting documents below it, per the below photo.  Very visual, very clear.

The second was that in James’s team meeting and in his 1:1 meeting, he consistently referenced the behaviors.  Key learning:  having values is great, making them come to life and be relevant for a team day-in, day-out is a lot harder but quite powerful when you get it right.

4. Managing by checklist.  I wrote about this topic a while ago here, but there is nothing like food service retail to demand this kind of attention to detail.  Wow.  They have checklists and standards for everything.  Adherence to standards is what keeps the place humming.  Key learning:  it feels like we have ~1% of the documentation of job processes that Pret does, and I’m thinking that as we get bigger and have people in more and more locations doing the same job, a little more documentation is probably in order to ensure consistency of delivery.

5. Extreme team-based and individual incentive compensation.  Team members start at $9/hour (22% above minimum wage that most competitors offer).  However, any week in which any individual store passes a Mystery Shopper test, the entire staff receives an incremental $2/hour for the whole week.  Any particular employee who is called out for outstanding service during a Mystery Shop receives a $100 bonus, or a $200 bonus if the store also passes the test.  The way the math works out, an entry level employee who gets the maximum bonus earns a 100% bonus for that week.  But the extra $2/hour per team member for a week seemed to be a powerful incentive across the board.  Key learning: team-based incentive comp is something we use here for executives, but maybe it’s worth considering for other teams as well.

6. Integrated systems.  Pret has basically one single software system that runs the whole business from inventory to labor scheduling to finances.  All data flows through it directly from point of sale or via manager single-entry.  All reports are available on demand.  The system is pretty slick.  There doesn’t seem to be much use of side systems and side spreadsheets, though I’m sure there are some.  Key learning: there’s a lot to be said for having a little more information standardized across the business, though the flip side is that this system is a single point of failure and also much less flexible than what we have.

7. Think time.  I’ve written a little about working “on the business, not in the business,” or what I call OTB time, once before, and I have another post queued up for later this summer about the same.  Brad Feld also very kindly wrote about it in reference to Return Path last week.  Working in retail means that time to work on IMPORTANT BUT NOT URGENT issues is extremely hard to come by and fragmented.  I suspect that it comes more at the end of the day for James, and it probably comes a lot more when he doesn’t have someone like me observing him and asking him questions.  But his “office” (below), exposed to the loud music and sounds and smells of the kitchen, certainly doesn’t lend itself to think time!  Key learning:  of course customers come first, but boy is it critical to make space to work OTB, not just ITB.  Oh, and James needs a new chair that’s more ergonomically compatible with his high countertop desk.

Years ago, I spent a few weekends working in my cousin Michael’s wine store in Hudson, NY, and I wrote up the experience in two different posts on this blog, the first one about the similarities between running a 2-person company and a 200-person company, and the second one about how in a small business, you have to wear one of every kind of hat there is.  My conclusion then was that there are more similarities than differences when it comes to running businesses of different types.  My conclusion from today is exactly the same, though the focus on management made for a very different experience.

Thanks to James, Gustavo, Orlanda, Shawona, and the rest of the team at the 36th & 5th Pret for putting up with the distraction of me for the bulk of the day today — I learned a lot (and particularly enjoyed the NYC Meatball Hot Wrap) and now have to figure out how to return the favor to you!

The Same, But Different

Mariquita and I spent several hours on the dueling laptops this evening.  It turned out, we were both working on OD things (Organization Development).

Mariquita’s project, for her Masters’ Program at Amercan U — was writing a lengthy paper on data collection and feedback as a major function of OD, as applied to a specific case of a startup going through growing pains (not Return Path…a case given by the teacher).  Her main comment — “they’ve got problems, man.”

I was working on an overhaul of Return Path’s management structure and what I call M/O/S (management operating system), based on the results of this year’s 360 Review process.  My main comment — “we’ve got problems, man.”  Well, not exactly in the same way, but we certainly have some major things to think through and change about the way we operate if we want to get the business to the next level.  The main topics were around preparing our organization — in terms of attitude, development, structure, and culture — to be 4x larger than it is today within a few years.

Interesting comparison.  Both valid uses of OD, totally different applications.

Counter Cliche:  Don’t Just Do Something, Stand There

Fred had a great posting the other day about Analysis Paralysis.  And he’s right, a lot of the time.  But I’ve always thought that Newton’s third law of motion can be applied to cliches — that every cliche has an equal and opposite cliche (think “Out of Sight, Out of Mind” vs. “Absence Makes the Heart Grow Fonder”).

The counter cliche to Analysis Paralysis is “Don’t Just Do Something, Stand There” — another great lesson taught to me by my old boss at MovieFone.  While startup businesses generally do need to move quickly and nimbly, there are times and places, particularly when negotiating something, where stopping or moving very slowly works to your advantage.  This can be true in any situation — hiring someone, working on a strategic partnership, acquiring a company or selling your own company, and yes, on occasion, even in closing business with a client.

Slowing down or stopping a negotiation helps you accomplish two critical things to achieving an optimal result:

1. It allows you to gain a little perspective on what you’re negotiating and consider other alternatives.  It’s easy to get caught up in the heat of a negotiation.  While that negotiating process can be addictive, you always want to make sure you really want what you’re going after and that you’ve taken every step you can to shore up your alternatives.

2. It lets you see how important the deal is to the other party.  If you change the pace of a negotiation, you can more easily see how the other party responds to that change of pace.  Do they fade away, or do they keep calling and pressing for forward movement?

There’s a time and a place for everything in a startup.  Sometimes it’s to run hard, but sometimes it’s to stand still.

Scaling Horizontally

Other CEOs ask me from time to time how we develop people at Return Path, how we scale our organization, how we make sure that we aren’t just hiring in new senior people as we grow larger.  And there are good answers to those questions – some of which I’ve written about before, some of which I’ll do in the future.

But one thing that occurred to me in a conversation with another CEO recently was that, equally important to the task of helping people scale by promoting them whenever possible is the task of recognizing when that can’t work, and figuring out another solution to retain and grow those people.  A couple other things I’ve written on this specific topic recently include:

The Peter Principle Applied to Management, which focuses on keeping people as individual contributors when they’re not able to move vertically into a management role within their function or department, and

You Can’t Teach a Cat How to Bark, But you Might be able to Teach it How to Walk on its Hind Legs, which talks about understanding people’s limitations.

Another important point to make here, though, is thinking about how to help employees scale horizontally instead of vertically (e.g., to more senior/management roles within their existing function or department).  Horizontally scaling is allowing employees to continue to grow and develop, and overtime, become more senior and more valuable to the organization, by moving into different roles on different teams.

We’ve had instances over the years of engineering managers becoming product managers; account managers becoming product managers; product managers becoming sales leaders; client operations people moving into marketing; account managers moving into sales; I could go on and on. We’ve even had executives switch departments or add completely new functions to their portfolio.

Moves like this don’t always work. You do have to make sure people have the aptitude for their new role. But when moves like this do work, they’re fantastic. You give people new challenges, keep them fresh and energized, bring new perspective to teams, and retain talent and knowledge.  And when you let someone scale horizontally, make sure to celebrate the move publicly so others know that kind of thing can be available… and be sure to reward the person for their knowledge and performance to date, even if they’re moving laterally within your org chart.

I help mentor CEOs on executive hiring all the time. One common refrain I hear when we’re talking about requirements for the job is about something I like to call The Mythical Playbook. If I only had the exec with the right playbook, thinks the hiring CEO, all my problems in that executive’s area would be magically solved.

I once hired a senior executive with that same mentality. They had the pedigree. They had taken a similar SaaS company in an adjacent space from $50mm to $250mm in revenue in a sub-group within their functional area. They had killer references who said they were ready to graduate to the C-level job. They had The Playbook! 

Suffice to say, things did not go as planned. I ignored an early sign of trouble, at my own peril. The exec came to me with a new org chart for the department, one with 45 people on it instead of the 20-25 who were currently there. I believed the department was understaffed but was surprised to see the magnitude of the ask. When I pushed back in general, the response I got was “I plan to overspend and overdeliver.” Hmm, ok. I don’t mind that, although a more detailed plan might be useful.  

Then I pushed back on a specific hire, pointing to a box in the org chart with a title that didn’t make sense to me. The response I got was “Yeah, I’m not entirely sure what that person does either, but I know I need that, trust me.” Yikes. 

There are two reasons why The Playbook is mythical. 

The first reason there’s no such thing as a Playbook for executives is that every situation is different. No two companies are identical in terms of offering or culture or structure. Even within the same industry, no two competitive landscapes are the same at different points in time. If life as a senior executive were as simple as following a Playbook, people would make a zillion dollars off publishing Playbooks, and senior executive jobs would be easier to do, and no one would get fired from them.

Now, I’m not saying there isn’t value in analogous experience. There is! But when hiring an executive, you’re not solely looking for someone who claims to know all the answers based on previous experience. That is a recipe for blindly following a pattern that might or might not exist. The value in the analogous experience is in knowing what things worked, sure, but more importantly in knowing when they worked, why they worked, under what conditions they worked, what alternatives were considered, and what things fell apart on the road to success. A Playbook is only useful if it can be applied thoughtfully and flexibly to new situations.

The second reason there’s no such thing as a Playbook when it comes to hiring executives is that the person who might have written the Playbook is actually not available for your job. Most CEOs start a search by saying, “I want to hire the person who took XYZ Famous Company from where I am today to 10x where I am today.” The problem with that is simple. That person is no longer available to you. They have made a ton of money, and they have moved beyond your job in their career progression. What you want is the person who worked for that person, or even one more layer down…or the person who that person WAS before they took the job at XYZ Famous Company. Those people are much harder to find. And when you find them, they don’t have the Playbook. They may have seen a couple chapters of it, but that’s about all.

In the end, the department I referenced above was more successful, but not because of adherence to the new exec’s entire Playbook. The Playbook got the department out over its skis – we overspent, but we did not overdeliver. The new exec ended up leaving the company before they could implement a lot, and that person’s successor ended up refocusing and rightsizing the department. That said, the best thing the department got out of the exec with the Playbook was their successor, which was huge — one element of a strong exec’s Playbook is how to build a machine as opposed to just playing whack-a-mole and solving problems haphazardly.

(Note – I am using the singular they in this and in other posts now, as Brad. Mahendra, and I chose to do in Startup Boards. I don’t love it, but it seems to be becoming the standard for gender neutral writing, plus it helps mask identities as well when I write posts like this.)

(This is the third post in the series… The first one When to Hire your first CMO is here, and What does Great Look Like in a CMO is here).

 In Startup CXO I wrote that I always think that the French Fry Theory can be applied to many things, usually other food items. The French Fry Theory is the idea that you always have room to eat one more fry and in my case I always do. But the same idea applies to marketing because you can always do “one more thing.” One more press release. One more piece of collateral. One more page on the corporate web site. One more newsletter. Trade show. Webinar. Research study. Ad. Search engine placement. Vendor. System. Speech. Take your pick.

The world we operate in is so dynamic that marketing (when done well) is nearly impossible to ever feel like you’re completely on top of and it’s near impossible to get closure. There’s always more to be done, and the trick to doing it well is knowing when to say “no” as much as when to charge into something. In my experience, CMOs who aren’t scaling well past the startup stage are the ones who typically do one or all of the following.

First, they’re stuck in “french fry mode” and treat all tasks like french fries. They focus on task execution (eating the next fry) and can’t pull up to think about whether they’re doing the right thing (should they be ordering another plate of fries?) and they are simply not scaling. If your CMO is constantly putting out fires that’s a sign that they may be too task-oriented and not strategic enough.

 Another sign that your CMO isn’t scaling is if they report on activity as opposed to outcomes. This is related to my prior point.  When all the world is a task list, then report-outs are just volumes of tasks but tasks are not the same as productivity or results.  I’m not sure why marketing ended up like this, but it’s frequently the only function in the company that spends time producing beautiful reports on all the stuff they do.  It probably comes from years of working with agencies who report like that to justify client spend.  Regardless, can you imagine seeing reports on activity instead of outcomes from other departments? Do you really need the report from the CFO that talks about how many collections calls the team made as opposed to reporting on bad debt? Or a report from the CRO talking about how many meetings a rep had with no mention of pipeline or closes – seriously?  No thank you.  CMOs who can’t link activity to outcome with a focus on outcome are not scaling with the job and for all you know they may be rearranging the chairs on the Titanic.

A final sign that your CMO isn’t scaling is if they spend disproportionate amounts of time on creative or agency work.  That’s the glamorous and fun part of marketing, for sure.  Having made TV commercials as a head of marketing when I was at MovieFone, I can attest to that.  But even if you’re a big B2C marketer with a lot of agency and creative spend, while you should be supervising that work, spending all your time on it is a sign that you’re not interested in all the other, well, french fries.

Marketing is becoming increasingly complex and differentiated, and it can easily be a service center as opposed to a strategic function. I don’t think that’s ideal, but that may be how a company decides to run it. But even if it is a service function your CMO needs to able to create space in their day for thinking and analysis, they need to be strategic, and they need to be able to stop doing “one more thing.”

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

My friend Seth has a theory about life called the French Fry Theory. The theory is simple — “you always have room for one more fry.” It’s pretty spot-on, if you think about it. Fries are so tasty, and so relatively small (most of the time), that it’s easy to just keep eating, and eating, and eating them.

I’ve always thought that the French Fry Theory can be applied to many things, usually other food items. However, I came up with a new application today: Marketing.

So why are French Fries like Marketing? You can always do one more thing. One more press release. One more piece of collateral. One more page on the corporate web site. One more newsletter. Trade show. Webinar. Research study. Ad. Search engine placement. Vendor. System. Speech. Take your pick.

The world we operate in is so dynamic that marketing (when done well) is nearly impossible to ever feel like you’re completely on top of. There’s always more to be done, and the trick to doing it well is knowing when to say “no” as much as when to charge into something.

My hat’s off to 21st century online-industry marketers. To bring this analogy back to its starting point…their plates are full!

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.