The Five Factors of Change

Why is it so hard for organizations to change? I ask myself this question frequently. Having helped build and invested in dozens of companies throughout my career, I’ve seen first hand how challenging it can be to drive real organizational transformation. Advising and coaching on organizational change can be even more difficult because every organization is different. No two are alike. The people are different. The cultures are different. The markets are different. The incentives are different and so on.

Earlier this week, I received a newsletter from my friends Noah Brier and James Gross. Noah and James are the co-founders of Percolate and recently founded a new company called Variance. Most of their time these days is spent thinking about how organizations solve real business problems and drive digital transformation through the adoption and utilization of software. For anyone familiar with Noah and his work, you know that he’s a connoisseur of frameworks and mental models.

As I was reading their newsletter, I was captivated by this framework which was introduced by Timothy Knoster in his 1993 white paper, ‘Reflections on Inclusion at School... and Beyond.’ Knoster applied his framework to driving change within educational institutions but I believe it’s relevant to organizations of all sizes and sectors.

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I spend a lot of my time coaching leaders on personal and organizational change so this mental model really resonated with me.

When I was digging into Knoster’s framework, I was struck by its power and simplicity. Organizations are complex systems with numerous moving parts and interdependencies. Knoster framework clearly shows that change isn’t driven by just one variable but a number of variables including vision, skills, incentives, resources and planning. He also shows that you need to make all of these things work together in order to drive change. For those of you out there who have led an organization, you’ll know that getting all of these to line up is no small feat.

If you have skills, incentives, resources and a plan but no vision you’ll get confusion. If you have all the elements described above but not the skills you’ll get anxiety. I think you get the point. Driving real organizational change is clearly multifaceted and complex.

In true Noah fashion, he took Knoster’s model one step further and made a compelling argument that leaders should think about each of these attributes as a slider rather than a binary switch:


Noah provided an excellent example using incentives to reinforce the interplay and sensitivity between these levers of change: “You don’t always need to dial up incentives to fix that problem. In fact, often it might be impossible, especially if those incentives are financial. So instead you may need to push up another one of your sliders to make up for the position of incentives. One particularly useful slider in these sorts of problems is vision: Helping people understand the larger context for why they’re being asked to do something that they may not be directly incentivized for can help them get over that issue. By doing that we can get ourselves back into equilibrium.”

If you’re a leader and you’re looking to drive transformation within your team or organization, I encourage you to experiment with these two frameworks to help you brainstorm, assess and implement potential solutions. I believe it will help you gain greater understanding of the drivers in your organization, design pragmatic solutions and help your change initiatives gain more momentum out of the gate.

To sign up for the Variance newsletter and receive insights like this from Noah and James click here.

John Wooden on Success

John Wooden is arguably the greatest men’s basketball coach of all time. He led UCLA to ten NCAA national championships in a 12-year span. Within this period, his teams won a NCAA men's basketball record 88 consecutive games.

Over the weekend, I was browsing YouTube and discovered his TED Talk from 2001. I watched the video twice because Coach Wooden’s views on success, leadership and winning are refreshing and inspiring, especially in an age where winning at all costs seems to be all that matters.

In this talk, he shares his own definition of success: “Peace of mind attained only through self satisfaction in knowing you made the effort to do the best of which you’re capable.” I encourage you to read that one more time. Let his words sink in.

Wooden’s definition of success isn’t about winning, losing, getting to the top of the mountain or having the most money. It’s all about finding inner peace and satisfaction knowing that you did the best you possibly could. I love that.

When he was growing up in Indiana on a farm with no electricity, his father use to say to him don’t whine, don’t complain, don’t make excuses…just get out there and do the best of your ability. There was no mention of winning. Coincidentally, my parents instilled a similar philosophy in my siblings and me when we were in high school.

I believe leaders from all types of organizations can learn from Coach Wooden’s perspective on success. At the end of the day, winning isn’t only what truly matters. Just as important is knowing that everyone on the team is working hard together, growing individually and putting in right effort to achieve a common goal.

There Is No Perfection

Yesterday, I went for a stroll in Madison Square Park with my friend Dan Kimmerling who was visiting from the west coast. Dan one of the most thoughtful, intelligent and empathetic seed investors I know. Every time I get together with him, I walk away with nuggets of wisdom, insight and/or inspiration about a range of topics including the venture business, startup life and philosophy.

We were discussing that nagging and unsettling feeling that many of us often experience when things don’t seem to be perfect in life. It’s that feeling that ultimately forces us to start considering big life decisions such as making a career change, starting a new venture, leaving a relationship, moving to a new city and so on.

Dan said something that stuck with me and has been on replay in my head over the last twenty four hours:

“There is no perfection. Don’t allow the desire for the future perfect to be the enemy of the present sufficient. Because the future perfect is an illusion, once achieved, will suggest yet another future perfect.”

I’ve fallen into this mental trap more times than I’d probably like to publicly admit. It’s so tempting and easy to find dissatisfaction in our lives especially living in New York where the markers of success are always in our face and constantly moving higher and higher.

That voice in our head is incessantly chirping away: If only I had a better job. If only I made more money. If only my company made these strategic changes. If only I were able to buy that fancy shirt. If only I could date that perfect person. If only my boss didn’t Slack me at 7am. If only I had my own fund. If only I could go to yoga in the middle of the day. If only. If only. If only.

As Dan pointed out, the future perfect is an illusion so once we arrive at that destination yet another one will emerge. We eventually find ourselves in a never ending quest to chase perfection. We never feel at home.

I’m not suggesting that we get complacent and put our hopes and dreams aside. I hope every single human on the planet is able to create a life that is filled with joy, happiness and fulfillment. I genuinely do. I’m purely suggesting that we become aware of when our future perfect is clouding our perspective and simply acknowledge that some goodness does exist in the present sufficient.

Inside the Mind of a New York VC

Earlier this summer, I sat down with Bart Clareman of AlleyWatch for a wide ranging interview. We talked about my accidental path to venture, the evolution of the tech ecosystem in NYC over the last decade, my human-centric approach to investing, how Primary provides a unique approach to supporting our founders and much more.

Below is the full transcript of the conversation. Enjoy!

Bart Clareman, AlleyWatch: Tell us about your journey into the venture business and how you came to be a partner at Primary Ventures?

Steve Schlafman, Primary Venture Partners: I would say that I didn’t really have the desire to become a venture capitalist, it all happened by accident. I was in the right place at the right time at a few points in my career. Luck and serendipity have definitely played a big part. I started my career at Microsoft, interning for six months on the Deal Governance team, which monitored all the strategic investments that Microsoft had made in the dotcom era. That was really my first exposure to the venture capital business.

After graduating from Northeastern University, I went back to Microsoft and spent four years working in Redmond [WA] and living in Seattle. The first two years was in a corporate finance-leadership rotation program where every six months I would rotate into a new area of finance. Then I spent two years effectively doing strategy and M&A for the Microsoft Business Division, which was responsible for Microsoft’s Business Applications such as Office and SharePoint.

After nearly five great years at Microsoft, I wanted to move closer to family and friends – I’m originally from Boston – and I wanted to get a taste of the startup life. That brought me to New York for a first tour of duty here in the city. I worked for a company called Massive, which was an advertising network for video games. It was the first ad platform for connected consoles and PC games. We worked with some of the largest publishers, including EA, Activision, and others, and served ads into games like Call of Duty and Madden. In this role, I was able to marry two of my passions: new media and video games.

I was about one year into my job at Massive, when an unexpected opportunity literally fell in my lap: I had a chance to move home to Boston to work for The Kraft Group. They own and operate the New England Patriots and a number of other businesses in sectors ranging from paper and packaging to real estate. My role at The Kraft Group was to support Mr. Kraft and his son Jonathan, who is the President & COO, on a variety of strategic projects that ranged from venture investments all the way through to digital media strategy to incubations to acquisitions and even random one-off projects. It was a perfect blend of investing, operating and strategy roles. I have to admit for a while it was my dream job. During this time, we made a number of direct investments into startups as well as some venture funds. This was my first real taste of the venture business. I owe a huge amount of gratitude to Mr. Kraft and Jonathan for giving me a shot. At the time, I didn’t really know what I was doing.

While I was at The Kraft Group, we made a number of investments and strategic partnerships with companies in the New York ecosystem. I saw first-hand the burgeoning community that was growing here and I wanted to be a part of it. It was impossible to ignore all of the startups and innovation that was happening here – around 2009 and 2010. As much as my wife and I loved being in Boston, we both knew New York was where we wanted to be long term. You could just feel the wave that was coming. Betaworks had just gotten formed, there were a handful of relatively new funds and some incredibly innovative companies were being started like FourSquare, Tumblr and Kickstarter to name a few.

I was recruited by Seth Goldstein and Billy Chasen to join an early startup as effectively the first business hire. It was called Stickybits, and it was backed by First Round Capital and Chris Sacca and a bunch of other well-known angels. I was effectively responsible for Business Development, Finance and other admin functions. I helped broker partnerships with Pepsi, Ben & Jerry’s, Unilever, Toyota and some other amazing brands. About nine months into my time at Stickybits, we pivoted into, so I lived through that whole experience. It went viral, but I ultimately didn’t want to be in the music business for a whole bunch of reasons. I like to joke that all of our servers were named after dead music ventures, so that was kind of the writing on the wall.

At that point, I had the very good fortune of joining Lerer Hippeau as the first investing principal. At the time it was four partners and an admin, and they brought me in to help build out a lot of the infrastructure for managing the deal pipeline and the support platform. It was a wild time.

I was at Lerer for roughly 2.5 years. While I was on the team, we made about 100 investments, 40-50% of which were in New York, the other half were spread throughout the rest of the country. We invested across every sector imaginable, including e-commerce, software as a service, hardware, healthcare, media, marketplaces, and everything in between.

After an amazing run at Lerer, I was recruited to join RRE Ventures to focus not just on Seed but also Series A. I figured it was a great opportunity to see which stage of investing, Seed or Series A, was right for me in the long term. I knew I loved Seed investing from my time at Lerer – we were effectively making an investment per week, if you can believe it. At RRE it was a more traditional Series A fund, where we made two to three investments per partner per year and no more than ten per year for the entire fund. Essentially, I wanted to know whether Seed or Series A investing was more compelling to me if I was going to make a career in venture capital.

My four years at RRE were incredibly productive. During that time, I sourced more than twenty investments and was on the Board of a handful of those companies. I was fortunate to partner with a pretty eclectic group of founders and companies, including Boom Aerospace, Bowery FarmingHightower (which merged with VTS), Giphy, Brightwheel, Managed by Q (sold to WeWork), Breather, Groups, theSkimm, Care/of, Citizen – those are some that come to mind. While I was there, I also made a number of angel investments in companies like Zipline and Lola.

I left RRE roughly 2 years ago. I took a year off to find myself and figure out what I wanted to do with the rest of my life. I actually considered leaving venture altogether for a variety of reasons. About three months after I had left RRE, I went back to school to get trained and certified as an executive coach. I just love nothing more than helping founders and executives in transition bring their visions to life.

After months of reflection and soul searching, I decided to join Primary Venture Partners which is one of the top seed funds here in New York City. I initially joined as a Venture Partner which allowed me to focus on both investing and coaching. But after three months, Ben and Brad convinced me to come on board as the third partner. I’ve now been at Primary for about fifteen months

My mission and my life’s work is to marry venture capital with human capital. The venture capital comes from deploying capital into companies, and the human capital comes through the leadership coaching and really focusing on a human approach to not only picking companies but also partnering with founders to help them navigate the everyday challenges of company building.

You’ve been in New York City’s venture investing community for nearly 10 years. How has the ecosystem here changed in that time?

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Adyashanti On Letting Go Of Fear

Last month, my friend Hursh introduced me to Adyashanti, the philosopher and spiritual teacher. I’ve been on break this week so decided to go down a rabbit hole and watch a number of his talks on YouTube.

This one on fear particularly resonated with me. Instead of fighting our fears, Adyashanti suggests slowing down, getting still, and relaxing into the knowledge that you will let go when the time is right and you are ready. He makes a compelling argument that there’s nothing to fear to begin with but we need to discover that ourselves by meeting that fear.

If you’re currently battling fear in your life, I invite and encourage you to take fifteen minutes to watch this short talk. It helped me shift my perspective and let go of a fear I’ve been holding onto for months. May it do the same for you.

Think Mystery, Not Mastery

Over the weekend, I attended a meditation retreat at Garrison Institute led by Sharon Salzberg and Ethan Nichtern. I can’t recommend this place enough. It’s one of the hidden gems of the Hudson Valley and only one hour north of the city.

After Sharon’s and Ethan’s talk on the first night, I was browsing the library and discovered the timeless classic The Artist Way by Julia Cameron. I have wanted to read this book for years. Since I’m trying to write more frequently, I decided to pick it up and dive in.

A few dozen pages into the book, the following line grabbed my attention: “Write what intrigues you, explore what interests you; think mystery, not mastery.” I repeated to myself, ‘Think mystery, not mastery,’ and then quickly wrote that phrase on a scrap of paper I carried in my pocket all weekend.

There’s something romantic and intoxicating about beginning a new hobby, craft or profession. We dream of penning that New York Times bestseller, performing in front of sold out crowds at Carnegie Hall, coaching a legendary Fortune 500 CEO and/or building a category defining company that touches millions. We feel like the sky is the limit and we can accomplish anything.

But soon after we get started, our inner critic runs wild on us and the learning curve begins to feel like a cliff. Or even better, we make initial progress but eventually hit the dreaded plateau that seems to stretch as far as the eye can see. Eventually we get that sinking feeling inside and reality sets in: becoming really good at [enter whatever skill or craft you’d like] is going to require a tremendous amount of time, energy, experimentation, mentorship, luck and failure. Gulp.

That’s why mystery is our friend. Mystery is the unknown. Mystery takes us to our edge. It’s at these outer limits where we grow and evolve. This is also the space where we find the confidence and faith in ourselves and our process. If we allow our true interests and curiosity to lead the way, we expand our boundaries through exploration, inquiry and experimentation.

Dreaming about and even obsessing over mastery early in our journeys can be debilitating and limiting. I’ve been there too many times to count on both hands. I haven’t found it to be productive in all these years.

That’s why ‘think mystery, not mastery’ is a useful mantra. It’s not about the light at the end of the tunnel. It’s about getting really curious about the tunnel each step of the way.

Parker Palmer On Vocation

I just finished reading ‘Let Your Life Speak’ by Parker J. Palmer. He’s an author, educator and activist focused on community, leadership, spirituality and personal growth.

The book is essentially a collection of Palmer’s essays about listening to your inner voice or true self, finding your vocation in life, crawling out of the depths of depression and finding the path towards meaning and fulfillment.

I found his essays to be deeply thought provoking and timely given I’m turning forty in October and wrestling with some big life questions. This book has helped me find some clarity by tuning into my inner voice, recognizing what gives me energy and asking myself what’s truly important.

There is one passage in the book that really struck a nerve for me. I wanted to share it with you in hope that it speaks to you as well.

“Vocation at it’s deepest level is, “This is something I can’t not do, for reasons I’m unable to explain to anyone else and don’t fully understand myself but that are nonetheless compelling.”

What is your vocation?

The March To 10,000 Hours

How long does it take to become a master at something? I first learned of the “10,000-Hour Rule” about a decade ago when I first read ‘Outliers’ by Malcolm Gladwell. The premise of this rule is simple: the key to achieving mastery in any skill or craft, is, largely, a matter of putting in the time and practicing for roughly 10,000 hours. Gladwell argued that legends like The Beatles, Bill Gates and others crossed this milestone before truly breaking out.

I’ve been thinking about the “10,000-Hour Rule” following a conversation I had a few weeks ago with a talented and thoughtful executive at a well known startup in NYC. This gentleman just turned thirty and is starting to think about the next phase of his career and life. Despite being very good at his job, he doesn’t feel like he has made an impact or developed real skills that are truly valued in the world.

He told me about Thomas Callahan, a bike builder in Brooklyn, who is the founder of Horse Cycles. Thomas makes about twenty custom steel bikes each year. His bikes are incredibly well made and beautiful. I can assure you Thomas has passed the 10,000 hour threshold building bikes. He’s a master craftsman.

My friend explained, “there’s something intoxicating about the idea of building something with my hands, delivering it to a customer, and then seeing that person derive happiness and meaning from that exchange.” I got the sense my friend desires to transition from his “desk job” to a new vocation that has a tangible impact on others. Thomas Callahan clearly has impacted my friend.

How does this story relate back to 10,000 hours? My friend just entered his thirties and is clearly contemplating what to do next with the next phase of his career and life. I don’t know what is the right answer and path for him. BUT I do know that he has the time to remake himself and master a craft if that’s what his heart truly desires. God willing he makes it to eighty, he has five decades remaining to devote to his craft. Five decades! That’s fifty years! The time no doubt will go fast but it’s certainly more enough to achieve mastery.

So what does the march towards 10,000 hours look like? Eight hours a day for five days a week gets you there in only five years. Seems challenging but doable especially if one switches careers. Here’s another combination: two hours a day for five days a week gets you there in twenty years. That’s the part-time path to 10,000. There is even a calculator should you want to go down that rabbit hole.

Here’s my point in all of this. We all have the ability to launch our lives in a different direction. We all have the ability to master a new craft. We all have the ability to bring our visions to life. 10,000 hours seems like an eternity but remember time is on our side for many of us especially if we get started today. Each of us can become our own version of Thomas Callahan if we’re willing to put in the effort, passion and of course the time behind a vocation that we truly love.


The Craftsman (And The Factory Worker)

The older I become, the louder the voice in my head is screaming, “Stop wasting time and create.” This voice talks to me when I’m on the subway, upstate in the woods and even when I’m in pitch meetings. For years, creative ideas have flooded my brain but I haven’t taken much action outside of penning blog posts every few months. Perhaps the voice is gaining power because I’m internalizing the fleeting nature of life, I badly want to create something from beginning to end, and/or want to leave something behind that’s truly an expression of myself.

Several weeks ago I was having my monthly ‘philosophical conversation’ with Andrew Taggart, a modern practical philosopher. He is three parts philosopher and one part coach. For months, we’ve been talking about creation and expression. These themes are top of mind as I turn forty in just two months. I want creation to define the next decade of my life. Andrew has been helping me examine this deep desire and explore how these urges will ultimately manifest in the world.

At the conclusion of our conversation, he sent me the following on ownership and creative freedom:

“A person is alienated just in case he doesn't, as it were, really see himself in what it is he makes. A simple example: a factory worker, Marx thought, was alienated, because of the division of labor: unlike a master craftsman, a factory worker does not place his creative stamp on the thing from beginning to end. A craftsman makes the entire violin. A factory worker may help manufacture the resin.”

This passage hit me like a ton of bricks. I wrote it in my journal immediately and I’ve been revisiting what it means to be a craftsman over the last few weeks.

A craftsman has complete control over his craft. He hones his specialty through years of trial, error and experimentation. He gets lost in his work. In fact, he doesn’t even feel like he’s working most of the time. He would refer to it as a vocation rather than work. Passion drives him rather than financial reward or upside. He’s satisfying his desire to make something out of nothing, to manifest his vision in the physical world, to push the boundaries of what’s possible. He is part of a community of craftsmen who help push his work. His fingerprints are found at every stage in the creation process. He will stand in the face of criticism no matter how brutal because the craft is the calling. A craftsman lives to create and to be one with his creation.

Frankly, I haven’t felt like a master craftsman with end-to-end ownership and creative freedom over a product and/or craft for a long time. Perhaps that’s because VCs are removed from the company building that’s taking place inside the portfolio. Perhaps I haven’t found the creative outlet that’s calling out to me. Perhaps I need to launch a creative project to grease the wheels. Perhaps VC is a creative craft and I need to shift my perspective. Perhaps coaching is that craft.

In the next two months before my fortieth birthday, I’m going reflect on how I want to spend the next decade of my life and what I want to create. More specifically, how do I want to spend my time and express myself? What do I want to leave behind? I don’t know where I’m going just yet but I do know that I’m committed to harness the power of the craftsman that lives inside of me.

Are you a craftsman? Do you see yourself in what you make? What’s calling out to you?

Creator Lab: On Personal & Professional Growth

Last month, I had the good fortune of sitting down with Bilal Zaidi of Creator Lab, a podcast that dissects the thoughts and actions of leading entrepreneurs, non-profit founders, award winning designers, educators, artists and everything else in between. Our episode dropped earlier this week (Apple, Spotify, Overcast).

In our wide ranging conversation, we discuss my journey to becoming a VC and a coach, what I look for in a venture investment and why Primary is the best seed fund for entrepreneurs in NYC. We also dive into how to navigate your career, why I decided to adopt a sober lifestyle (hint: performance + clarity), how to create good habits, why the top performers have coaches, how I’ve coped with anxiety and the fear of death, and why 360 reviews are a powerful tool to uncover your blindspots.

This was a really fun and open discussion. I certainly didn’t hold back. I hope you walk away inspired to build the future you’re craving, make changes in your own life and/or help someone you care about. Enjoy!

How To Conduct A Comprehensive Annual Review

“Without reflection, we go blindly on our way, creating more unintended consequences, and failing to achieve anything useful.” -Meg Wheatley

The holiday season is my favorite time of the year. It symbolizes family, friends, vacation and of course plenty of good food. I also enjoy it because it marks the end of the year and the beginning of a new one. This is an ideal moment to reflect on the past twelve months and to define what we want to achieve in the year ahead.

So much happens over the course of a year. Lessons learned. Victories. Hardships. Physical changes. Special moments. Personal growth. New relationships. But by the time New Year’s rolls around, we often forget most of what happened because life gets in the way.

Many of our employers have us complete an annual review and set goals before year end. This makes good sense. It’s difficult to know where to head if we don’t know where we’ve been. But this leads me to the question: why don’t we conduct an annual review for all the components of our life? The answer is simple: we don’t create the time necessary, feel any pressure to or have a blueprint to guide us.

For the last three years, I’ve carved out time at the end of the year to conduct a comprehensive annual life review. The process has been not only cathartic but also illuminating and empowering. In fact, this exercise has helped me identify what’s important, shed what isn’t, and transform in many ways. As a result, I decided to get sober, leave a job that wasn’t the right fit and pursue coaching as a profession.

Several clients and friends recently asked me to share my annual life review blueprint. What follows is an attempt to provide the framework and hopefully the nudge to complete your own annual life review.

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On Privilege

Last week, I published a blog post titled, ‘Decoding the Qualities of a Great VC.’ The spirit behind the piece was to spark a conversation about what makes a good venture investor and whether that can be predicted. It was generally well received until I saw this Tweet from Nathalie Molina Nino, CEO of BRAVA Investments, an investment platform that cares less about creating the next woman billionaire and instead backs businesses that create wealth for a billion women.

I immediately became defensive because I had good intentions in writing the post and felt I highlighted ‘universal’ attributes of great investors. Without giving it any thought, I quickly replied to Nathalie with the following tweet.

I then felt a backlash from a number of individuals including Katherine Gordon, Founder of The 3% Conference.

At that point, I became uncomfortable because my ignorance was obvious. Growing up in a predominately white upper middle class town in Massachusetts, I was indirectly taught that privilege was about wealth rather than race, gender, sexual preference, etc.. I incorrectly believed I wasn’t privileged because a) I was raised by an amazing single mother who worked two blue-collar jobs, b) I’ve earned an income since my early teens, c) I financed my college education, d) and I’ve worked hard to be self supporting for nearly two decades. It dawned on me through those various exchanges that I have been eating my own bullshit. What I began to quickly realize is that wealth is just one component of privilege and arguably the weakest one.

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