The last couple weeks, I’ve written about tools in the CEO toolbelt that I learned with my coach Marc years ago in a workshop called Action/Design — Inquiry vs. Advocacy, and The Ladder of Inference. The final post in this series is about Learning Loops (or Double Loop Learning if you prefer), popularized by Chris Argyris a couple decades ago.

Here’s the graphic on it:

What’s the tool in the CEO toolbelt here? It’s that every time you’re analyzing a result, you need to analyze it on two levels. Level 1 is the more obvious learning — “What happened…and what do I do next time to produce the same/a different result?” Level 2 is the less obvious learning — “Why did that result happen, and how do I need to think differently about the problem in the future?”

Think about how to apply this to a business result. You put a new pricing plan in place. Clients don’t bite. Loop 1 just gets you something like “ok, let’s try a different pricing plan.” But Loop 2 gets you “how did we come up with the pricing plan that failed in the first place…and how do we generate the next one so we don’t fail?”

Or think of how to apply this to a difficult conversation. You and your VP Eng on why a critical engineer left your organization abruptly. Your VP Eng is blaming Product for poor management of the agile process and product design; you believe it’s an issue of engineering team burnout. You can just go back and forth Advocating your points of view and maybe even Inquiring as to why those points of view exist, and even the powerful Ladder of Inference may not be able to help unless you have a great exit interview. Double Loop Learning is an offramp from that kind of conversation in that you can add that Level 2 questioning to the mix. It’s not about “what do we tweak so another engineer doesn’t leave tomorrow.” It’s “is there a systemic problem here with the way we produce product (or even broader – with our product/market fit) that doesn’t encourage the best team members to stay here?”

The best CEOs are the ones who are constantly listening, learning, adjusting, and executing. Hopefully these three principles — Learning Loops, Inquiry vs. Advocacy, and The Ladder of Inference will all help you on your journey.

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!

Here’s one to keep in mind – we did this a few times at Return Path, and I was just reminded of it when I was coaching another founder who is doing the same thing right now.

Sometimes when you’re doing a strategic acquisition and it’s an all-stock deal, you can insist as a term of the acquisition that the target company’s investors invest more capital into your company.

That’s right, not only do you not have to put cash OUT for the deal, you’re getting additional cash IN. Think of it as a contemporary corporate version of the dowry.

Why would the cap table of the target company agree to this? Here are a few reasons:

• you’re in a strong enough negotiating position – best home for the business, best chance of the target company investors getting a return
• the target company investors have more dry powder and want to double down – they love your vision for the combined company
• you’re only offering the target company investors common stock in the deal, and they are pushing hard to get preferred

The Dowry is not something you can get to with every deal, and you might not need it. But think of it as a tool in the M&A/financing tool belt.

The Art of the Post-Mortem

It has a bunch of names — the After-Action Review, the Critical Incident Review, the plain old Post-Mortem — but whatever you call it, it’s an absolute management best practice to follow when something has gone wrong. We just came out of one relating to last fall’s well document phishing attack, and boy was it productive and cathartic.

In this case, our general takeaway was that our response went reasonably well, but we could have been more prepared or done more up front to prevent it from happening in the first place.  We derived some fantastic learnings from the Post-Mortem, and true to our culture, it was full of finger-pointing at oneself, not at others, so it was not a contentious meeting.  Here are my best practices for Post-Mortems, for what it’s worth:

• Timing:  the Post-Mortem should be held after the fire has stopped burning, by several weeks, so that members of the group have time to gather perspective on what happened…but not so far out that they forget what happened and why.  Set the stage for a Post-Mortem while in crisis (note publicly that you’ll do one) and encourage team members to record thoughts along the way for maximum impact
• Length:  the Post-Mortem session has to be at least 90 minutes, maybe as much as 3 hours, to get everything out on the table
• Agenda format:  ours includes the following sections…Common understanding of what happened and why…My role…What worked well…What could have been done better…What are my most important learnings
• Participants:  err on the wide of including too many people.  Invite people who would learn from observing, even if they weren’t on the crisis response team
• Use an outside facilitator:  a MUST.  Thanks to Marc Maltz from Triad Consulting, as always, for helping us facilitate this one and drive the agenda
• Your role as leader:  set the tone by opening and closing the meeting and thanking the leaders of the response team.  Ask questions as needed, but be careful not to dominate the conversation
• Publish notes:  we will publish our notes from this Post-Mortem not just to the team, but to the entire organization, with some kind of digestible executive summary and next actions

When done well, these kinds of meetings not only surface good learnings, they also help an organization maintain momentum on a project that is no longer in crisis mode, and therefore at risk of fading into the twilight before all its work is done.  Hopefully that happened for us today.

The origins of the Post-Mortem are with the military, who routinely use this kind of process to debrief people on the front lines.  But its management application is essential to any high performing, learning organization.

The Nachos Don’t Have Enough Beef in Them

Short story, two powerful lessons.

Story:  I’m sitting at the bar of Sam Snead’s Tavern in Port St. Lucie, Florida, having dinner solo while I wait for my friend to arrive.  I ask the bartender where he’s from, since he has a slight accent.  Nice conversation about how life is rough in Belfast and thank goodness for the American dream.  I ask him what to order for dinner and tell him a couple menu items I’m contemplating.  He says, “I don’t know why they don’t listen to me.  I keep telling them that all the people here say that the nachos aren’t good because they don’t have enough beef in them.”  I order something else.  Five minutes later, someone else pounds his hand on the bar and barks out “Give me a Heineken and a plate of nachos.”  The bartender enters the order into the point-of-sale system.

Lesson 1:  Listen to your front-line employees – in fact, make them your customer research team.  I’ve seen and heard this time and again.  Employees deal with unhappy customers, then roll their eyes, knowing full well about all the problems the customers are encountering, and also believing that management either knows already or doesn’t care.  Or both.  There’s no reason for this!  At a minimum, you should always listen to your customer-facing employees, internalize the feedback, and act on it.  They hear and see it all.  Next best prize – ask them questions.  Better yet – get them to actively solicit customer feedback.

Lesson 2:  Always remember another person’s person-ness, especially if he or she is in a service role.  The old story about the waiter spitting and coughing in the obnoxious customer’s soup would dictate that self-preservation, if nothing else, should inspire civility towards people who are serving you, be it a B2B account manager or a waiter in a diner.  Next best prize – self-interest to get a higher level of service.  Better yet – engagement and kindness like you’d want people to show you.  Chances are, they’re trying to make your day a bit better.  Shouldn’t you try to do the same for theirs?

(Lesson 3:  Always listen to your bartender!)

I’ve always thought that the ability to stare down adversity in business — or turning lemons into lemonade, as a former boss of mine used to say — is a critical part of being a mature professional. We had a prime example of this a couple weeks ago at Return Path.

We had scheduled a webinar on email deliverability, a critical topic for our market, and the moment of the webinar had come, with over 100 clients and prospects on the line for the audio and web conference. There was a major technical glitch with our provider, Webex (no link for you, Webex), and after 5 or 10 minutes, we had to cancel the webinar — telling all 100 members of our target audience that we were sorry, we’d have to reschedule. What a nightmare! Even worse, Webex displayed atrocious customer service to us, not apologizing for the problem, blaming it on us (as if somehow it was our fault that half the people on the line couldn’t hear anything), and not offering us any compensation for the situation.

As you can imagine, our marketing guru Jennifer Wilson was devastated. But instead of sulking, she turned the situation on its head. She rescheduled the event for three weeks out with a different provider who was technically competent and a pleasure to work with, Raindance, and sent every person who’d been on our aborted webinar a gift certificate to Starbucks so they could enjoy a snack on our dime during the rescheduled event. Not only did we have full attendance at the rescheduled event, but Jennifer received dozens of emails from clients sympathizing with her, commending her on her attitude, and of course thanking her for the free latte.

It’s hard to do, and you hate to have to do it, but successfully turning lemons into lemonade is one of the most satisfying feelings in business!

People rarely comment on this blog (or most non-political blogs, I’ve noticed), so feel free to share your best lemons-to-lemonade story with me in a comment, and I promise I’ll post the best couple of them pronto!

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

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

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

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

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

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

You’ll learn:

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Counter Cliche:  Good Choices Are Made From Good Options

The Counter Cliche to Fred’s VC Cliche of the Week this week, the Walk Away,  is that Good Choices Are Made From Good Options.  Fred’s right — sometimes you do have to walk away from a deal where you’ve invested a lot of time, energy, and emotion.  But as an entrepreneur, you can mitigate the number of times you have to Walk Away by developing good alternative options to a particular deal.  That way, if one option doesn’t pan out as you’d hoped, another very good option is waiting in the wings.

There’s a very business school-sounding term called the BATNA, which stands for the Best Alternative to a Negotiated Agreement.  Quite frankly, it’s just a fancy way of saying Plan B.  I wrote about the importance of the BATNA once before in How To Negotiate a Term Sheet with a VC (item 3). 

Dying to get a deal with a good VC?  If you negotiate with one of them, you may or may not end up with a deal you like, and it could suddenly change on you at the 11th hour.  If you negotiate with two or three of them, you’ll have a great backstop and won’t let the emotional investment in the deal get the best of you.  Trying to sell a company?  You’d better have a couple of acquirers in mind to maximize price. 

Sometimes, developing a good BATNA, or Plan B, can take as much time as working on Plan A.  But it’s well worth it if it ensures that you will have multiple Good Options at the end of the process — which will invariably result in a Good Choice.

I think the lesson of the BATNA is more broadly true in life, not just in business, although it may be a little bit less universally applicable to VCs looking to put money to work unless there are multiple strong companies in a sector all looking for VC around the same time.

Playing Offense vs. Playing Defense

I hate playing defense in business.  It doesn’t happen all the time.  But being behind a competitor in terms of feature development, scrambling to do custom work for a large client, or doing an acquisition because you’re getting blocked out of an emerging space – whatever it is, it just feels rotten when it comes up.  It’s someone else dictating your strategy, tactics, and resource allocation; their agenda, not yours.  It’s a scramble.  And when the work is done, it’s hard to feel great about it, even if it’s required and well done.  That said, sometimes you don’t have a choice and have to play defense.

Playing offense, of course, is what it’s all about.  Your terms, your timetable, your innovation or opportunity creation, your smile knowing you’re leading the industry and making others course correct or play catch-up.

This topic of playing defense has come up a few times lately, both at Return Path and at other companies I advise, and my conclusion (other than that “sometimes you just have to bite the bullet”) is that the best thing you can do when you’re behind is to turn a situation from defense into a combination of defense and offense and change the game a little bit.  Here are a few examples:

• You’re about to lose a big customer unless you develop a bunch of custom features ASAP –> use that work as prototype to a broader deployment of the new features across your product set.  Example:  Rumor has it that Groupware was started as a series of custom projects Lotus was doing for one of its big installations of Notes
• Your competitor introduces new sub-features that are of the “arms race” nature (more, more, more!) –> instead of working to get to parity, add new functionality that changes the value proposition of the whole feature set.  Example:  Google Docs doesn’t need to match Microsoft Office feature for feature, as its value proposition is about the cloud
• Your accounting software blows up.  Ugh.  What a pain to have to redo internal system like that – a total time sink.  Use the opportunity to shift from a new version of the same old school installed package you used to run, with dedicated hardware, database, and support costs to a new, sleek, lightweight on-demand package that saves you time and money in the long run

I guess the old adage is true:  The best defense IS, in fact, a good offense.

I Love My Job

The picture below is a picture of my dress shoes in my closet at home.  You may note that they all have dust on them.  That's because I didn't put them on once for six weeks.

When we started Return Path back in 1999, we sat down to write our employee handbook, and all I could think was "what things can we add in here that will make this company a unique place to work?"  And one of them was a six week paid sabbatical after 7 years.  It didn't occur to me that we'd even exist after 7 years.  Then for good measure, we said, "7 years and every 5 years after that."

I'm happy to report that everyone who has hit their 7 year anniversary has taken the time off.  Some have traveled around the world, some have rented a house or villa somewhere, others (like me) did a "stay-cation."  Although my sabbatical was delayed (and quite hard to schedule), it was a fantastic experience.  I completely unplugged from work.  Cold turkey.  No email, no calls.  Spending time with Mariquita and my kids, which I never get to do much of, was completely refreshing and energizing.  And everything went fine at work, as I expected.  Business is in the best shape it's ever been in, and my amazingly talented executive team and assistant handled everything without missing a beat.

But back to the subject line of this post.  I figured a few things out while I was away.  One was that I haven't actually become a workaholic over the years despite working hard.  I *could* unplug without feeling aimless.  Another was that it's really nice to be untethered from the Internet, but it's near impossible to go through life now without some minor usage of the web and messaging.  But by far my biggest insight is plain and simple:  I love my job.  It's not that I didn't know that before, but I had more thoughtful time to break that down while I was away:

1. I love what I do:  I consider myself extremely fortunate to love the substance of my job.  The diversity of experiences that I have within a given week or day as a general manager, the interactions with people, shaping the business strategy, travel — it's all right up my alley. So many people out there don't have that match between interest, passion, skill, and reality. 

2. I love who I work with:  I have to admit that I stack the deck here since I do the hiring and firing, but the reality is that my colleagues at work are also my friends.  Not working was one thing.  Not talking to one particular subset of my life for six weeks was something else and just plain weird.  I just missed them and the interactions we have, which always blend the professional with the social. 

3. I love what we are working on:  We have an incredibly interesting business at Return Path.  It's very intellectually engaging, sometimes to a fault.  The spam problem is incredibly complex, and we're coming up with some extremely innovative approaches to reduce its impacts and hopefully someday eradicate it.  We're not curing cancer as I always say internally, but we're also engaged in some high impact problem solving that I just love.

So there you have it.  My work shoes are now dusted off and back in action.  It's great to be back.  We'll see how long I can stay in "mental vacation" mode, how much more time I can try to make for my family now that I'm back in my work routine, and whether the fresh perspective translates into any new actions or decisions at work.  But the best thought of all is that my 12 year anniversary is only another year and a half away!

Yiddish for Business

Contrary to popular belief, Yiddish isn’t “Jewish slang” (I hear that a lot).  According to Wikipedia, Yiddish is a basically a High Germanic language with Hebrew influence of Ashkenazi Jewish origin, spoken throughout the world. It developed as a fusion of German dialects with Hebrew, Aramaic, Slavic languages and traces of Romance languages.  It is written in the Hebrew alphabet.

I don’t speak Yiddish.  Like many American Jews whose families came to America in the late 19^th and early 20^th centuries, my grandparents spoke it somewhat, or at least had a ton of phrases they wove into everyday speech.  Presumably their parents spoke it fluently before coming here and Americanizing their families.  My own parents have a handful of stock phrases down.  My brother and I have even less.

What I like best about Yiddish is that I find it to be a very descriptive and also onomatopoetic language.  I can never verbally describe a Yiddish word without a lengthy description and some examples, and usually some level of gesticulation.  I’ll try to be more succinct below.  But in the end, words mean a lot like what they sound like they should mean.  A lot of New Yorkers who aren’t Jewish end up knowing a handful of Yiddish words because they’re pretty prevalent in the City, but many people outside New York don’t.  So I thought I’d have a little fun here and do something different on the 6^th anniversary of launching this blog (today) and list out some of my favorite Yiddish words and describe them with a business context.  In no particular order…

–          Schmooze – to chat someone up, work them, frequently with some kind of hidden agenda in mind.  Business application:  “She showed up at the charity event just to schmooze Alice, who was a potential client.”

–          Chutzpah – nerve, as in “wow, he has some nerve.”  My dad always said the classic description of chutzpah was the kid who murdered both of his parents, then pleaded with the judge for leniency because he’s an orphan.  Business application:  “He missed all his goals this quarter and asked for his full bonus and a raise?  Now that takes real chutzpah!”

–          Spiel (pronounced schpeel) – a monologue or lengthy pitch.  Business application:  “I’m raising money, so I have to really organize my spiel before I go talk to the VCs.”

–          Schtick – someone’s standard song-and-dance.  Business application:  “I stood up in front of the room and gave my usual schtick about our values and mission.”  Kind of like Spiel.

–          Schlep – to make a long, pain-in-the-ass kind of trip.  Business application:  “I had to schlep all the way to Toledo for a meeting with that guy, and he didn’t even end up signing the deal.”

–          Mazel tov – literally means “good luck” but usually used in regular conversation to mean “congratulations.”  Business application:  “You got a promotion?  Mazel tov!”

–          Noodge – someone who inserts himself into a conversation in a somewhat unwelcome manner.  Related to Kibbitz – to give unsolicited advice from the sidelines. Business application:  “Sally is such a noodge.  She kibbitzes about my unit’s strategy all the time and just stirs up trouble.”

–          Maven – an expert, even a self-styled one, in a very niche area.  Business application:  “You want to figure out what smartphone to  buy?  Ask Fred – he’s the maven.”

–          Kosher (a Hebrew word as well) – completely by the books, originally referring to dietary laws that religious Jews follow.  Business application:  “Ask Marketing if it’s kosher to use our partner’s logo like that.”

–          Verklempt – choked up, overcome.  Business application:  “When I got my review and promotion and raise, I was so verklempt that I couldn’t speak for a minute or two.”

–          Schlock, Dreck, Chazerai, Bupkis – all have slightly different literal meanings (apparently Bupkis means “goat droppings”), but I use all of them somewhat interchangeably to mean junk or something of limited or no value.  Business application:  “That presentation was nothing but chazerai.  What did I get out of it?  Bupkis.”

–          Kvell – to beam or burst with pride, related to Nachus – warm “gooey” feeling of pride.  Business application:  “I had so much nachus when my company won that award for being the best place to work, I was just kvelling.”

–          Mishegas or Bubbamyseh – craziness or self-imposed silliness.  You might have heard the word Meshugenah before, which means crazy.  Business application:  “I can’t get all caught up in his mishegas.  I’m going to make my own decision here.”

–          Kvetch – either a noun or verb meaning complain, in a harpy kind of way.  Business application:  “Frank is such a kvetch.  He is just never happy.”

–          Mensch – a good guy.  Business application:  “Michael is such a mensch.  He always helps his colleagues out even when he doesn’t have to or doesn’t get credit for it.”

–          Fercockt (pronounced Fuh-cocktah) – crazy, messy.  Business application:  “John’s project plan is totally fercockt.  No one can follow it even when he tries to explain it.”

–          Mishpochah – family.  Business application:  “Welcome to the company – we’re happy to have you in the mishpochah.”

–          Tsuris – heartache or sadness.  Business application:  “Boy that’s one client that gives me nothing but tsuris.”

–          Tchotchke (pronounced chach-kee) – a trinket or little toy.  Business application:  “What kinds of tchotchkes are we giving away at our booth at the upcoming trade show?”

Pull one of these out in your next meeting – see what it gets you!