Everything Is Hard

Earlier this week, my friend Julien Smith, Co-Founder and Chairman of Breather, posted the following tweet.

Julien knows better than just about anyone on the planet how challenging it can be to build a company with a digital AND physical product. The operational complexities and capital requirements are unique.

In that moment, Julien’s tweet reminded me of a recent exchange with Joshua Browder, the dynamic and talented founder of Do Not Pay. I sent him a note to congratulate him on his recent funding and to wish him good luck in the next phase of the company. He remarked, “Thank you so much! It’s a very tough company to build.” Josh and co are building real technology using “bits” as Julien put it. That’s hard too.

I then remembered a conversation I had with Justin Kalifowitz, CEO of Downtown Music, several years ago. Downtown is arguably one of the leading music rights management companies in the world. Justin and I were talking about the variety of challenges of running a business. He said something during our breakfast that has stuck with me, “Everything is hard.

Scaling a distributed co-working company is hard. Just ask Julien. Creating a robo lawyer to fight for consumers is hard. Just ask Mr Browder. Acquiring and monetizing music rights is hard. Just ask Justin.

You know what else is hard? Getting the guts to quit your job and start a business. Finding the right co-founders. Building a sustainable business as a freelancer / micro entrepreneur. Finding product market fit. Acquiring customers at scale. Developing real technical innovation. Timing the market perfectly. Convincing investors to give you huge sums of money every 12-18 months. Mustering the fortitude to march ahead when growth isn’t up and to the right. Building a brand that resonates with customers. Developing mutually beneficial strategic partnerships. Hiring, scaling and motivating a team. Achieving profitability. Growing and fostering a community. Managing and surviving the emotional ups and downs. Hell, even building a VC firm is hard.

Everything is hard.

I’m not here to discourage or dissuade aspiring entrepreneurs. You should absolutely sprint towards your vision and dream as fast as you can. Nothing should hold you back if you truly believe in yourself and the opportunity. Go for it.

Here’s my point: every single entrepreneurial journey is difficult and has twists, turns, ups and downs. It doesn’t matter if it’s your first or fifth company, an atom or bit based product, bootstrapped or venture backed startup. Every business is unique and has its own challenges. There’s no such thing as a walk in a park.

That’s why it’s critical to surround yourself with people who will offer unwavering support throughout the journey. This includes friends, advisors, mentors, other founders, mastermind groups, coaches, and therapists. Don’t underestimate the power of having neutral supporters in your corner to act as sounding boards and help you manage the ups and downs. It’s priceless.

My former partner, Eric Hippeau, always used to say, “It takes a village to raise a startup.” I couldn’t agree more.

Everything is hard but you can make the journey a bit easier by building and leveraging your very own support team and/or personal board of directors. You won’t regret it.

I Got A 360° Review. Here Are My Results.

Earlier this year, my partners Ben and Brad pulled me aside and explained they were hiring a coach to assess their leadership effectiveness and help them identify areas for personal and professional growth. The coach used a tool called The Leadership Circle Profile (LCP), a 360° assessment that measures and provides leaders feedback through the lens of what’s called the Universal Model of Leadership. More than 200,00 leaders throughout the globe have taken The LCP.

After learning more about The LCP and talking with Ben and Brad, I decided to jump into the fray and take the assessment. My experience was incredibly humbling, illuminating, empowering and impactful. I’d even venture to say that it was the most impactful professional development exercise I’ve completed in the past decade. In fact, I got so much out of my 360° that I recently became certified in The LCP with the goal of helping founders in the Primary portfolio and the NYC tech community become stronger and more effective leaders.

There are many leadership and personality assessments that are used throughout Corporate America and the startup ecosystem - MBTI, Enneagram, Emergenetics, Strengths Finder, Clifton Strengths and so on. There are also a number of 360° profiles to help leaders identify their strengths and opportunities for development. Most focus on management style and personality, competencies, OR underlying tendencies. The LCP combines all three of these areas into one comprehensive, accessible tool.

The LCP is the only tool to my knowledge that measures the two primary leadership domains – creative competencies and reactive tendencies – and then presents this information in a digestible format so that opportunities for development can rise to the surface. Here is a high-level snapshot of The LCP:


As you can see, the profile has northern and southern hemispheres. The northern focuses on creative competencies and the southern focuses on reactive tendencies. If your turn your attention to the outer circle, there are eighteen creative competencies and eleven reactive tendencies for a total of twenty nine leadership dimensions. These rollup to the nine summary dimensions found in the inner circle. It’s important to note that you shouldn’t think of creative as good and reactive bad. There are some nuances.

Creative competencies are linked to how a leader achieves results, brings out the best in others, leads with vision, enhances their own development, acts with integrity, and improves organizational systems. High scores in this hemisphere correlate to higher levels of leadership effectiveness and subsequently high levels of business performance. These creative competencies can be developed and enhanced over time through training, experience and mentorship.

Reactive tendencies emphasize gaining the approval of others, protecting oneself, and getting results through high control tactics. High scores in the reactive dimensions correlate to lower levels of leadership effectiveness. There are certainly gifts and costs associated with these tendencies. Again, one shouldn’t think of these as “bad” or negative. These tendencies are often developed earlier in life and we’ve used them to survive and even thrive in the world!

Here’s some good news: none of us are fixed and there’s quantitative proof that a leader can morph from reactive to creative. That’s what leadership development is all about.

You’re probably wondering by now, what was Schlaf’s experience with The LCP and what did he learn?

The end-to-end process took roughly forty five days and I personally invested about six to eight hours. This included selecting roughly twenty reviewers (my partners, peers, former colleagues and founders I’ve served), taking the assessment, reviewing the report and reading the reviewer’s comments, spending several sessions with a coach and then working on my development plan. Looking back, the investment in time and money was a no brainer.

The finished report was quite extensive. The package included my leadership circle, written qualitative feedback from the reviewers and the specific scores and how those compared to a range of benchmarks. Shortly after receiving my LCP results in the mail, I spent ninety minutes with my coach reviewing the results. Thank goodness. This gave me a chance to ask questions about The LCP, discuss the results and create a development plan. Candidly, it was a tough pill to swallow but very valuable. I’m still processing all of my learnings.

Below are my leadership circle results. Before you jump in, I’d like to share a few important points so you can make sense of the infographic. First, the green shading represents the scores from the reviewers while the dark black lines represent the scores I gave myself. Second, the scoring is relative so I’m effectively being compared to the 200,000 leaders in the database on a 0-100 percentile scale.

As you review the profile, I encourage you to look for high and low scores AND any large gaps between how I rated myself and how others rated me. That’s a good place to start.

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As you likely can see, I’m more reactive than creative. Within the reactive hemisphere, I was rated particularly high in the complying and the protecting categories. This includes specific tendencies such as pleasing, passive, distance, arrogance and ambition.

It’s clear that a number of these reactive tendencies have been holding me back as a leader. When I debriefed with my coach to walk through the results and determine my development plan, I decided to focus on pleasing and arrogance. I believed these two were causing the most damage and limiting my potential more than any others.

The tendency to people please has made it challenging to achieve results over the years. I’m often saying yes to things that don’t really map to my objectives and priorities. I want to help others and be liked so I have a hard time setting boundaries. This tendency has also made it difficult to live in accordance with my core values because I’m not always following what’s truly important to me.

Arrogance has limited my effectiveness because I can tune out and talk over people at times. Part of this has to do with impatience but also stems from my ADD which I’ve had my entire life. I also get excited and blurt things out so that behavior is misconstrued as impolite and inconsiderate. Given my ADD, I’ve struggled with concentrating in very long meetings which can make me seem distant and unfocused. Interestingly, these tendencies tend to surface in group settings and when I’m wearing my VC hat rather than my coaching hat.

When I first reviewed the “areas of development” written comments from my reviewers, I was embarrassed and disappointed in myself. I honestly felt like a failure and an imposter. I also had some resentment towards my colleagues who completed the assessment. I believe these are all natural and reasonable initial reactions. But after the debrief with my coach, I was able to take a deep breath, look at the results with some distance and view this as a real learning opportunity.

When looking at the creative hemisphere, I scored high in caring connection, balance and community concern. These were not much a surprise to me because I love people and relationships, believe strongly in the power of community and value balance in life. These are definitely core to who I am.

My coach encouraged me to spend time reviewing the section with the positive written comments. She said that I won’t get much value from the experience if I just focus on the reactive. Many of the comments were centered around my positive energy, ability to build deep and authentic relationships with founders, love and desire for community, knack to spot and invest in talent, and positive reputation in NYC tech. Reviewing these comments several times helped me see my superpowers from the perspective of my colleagues.

So what actions am I taking to ensure that my strongest reactive tendencies are minimized and I strengthen several creative competencies?

Right now, I’m incredibly focused on actions that map to my values (integrity), my objectives (achieves results) and the success and health of the organization (selfless leader). More specifically, I’m saying no more often and I’m protecting my calendar. Setting boundaries has become essential. I’m also blocking ninety minutes every morning to focus on high priority projects. Finally, I’m trying to ask myself the question, “what actions can I take that put the organization’s needs before my own.”

I had such a profound experience that I recently became certified in The LCP. As you can probably tell, I’m a huge believer in the power of the tool and process. I’m now able to deliver a similar experience to leaders throughout the Primary portfolio and the NYC tech ecosystem. I decided to add The LCP to my coaching tool belt because I fundamentally believe stronger leaders build stronger organizations. This is directly tied to one of my personal missions: to help leaders bring their visions to life.

I’m already seeing and feeling a huge difference in how I’m showing up at work and at home. The LCP reminded me that I’m human and far from perfect, but it also showed me that I have some amazing strengths and untapped potential. I’m proud of who I’ve become but I also recognize there’s tremendous room for growth. This last thought excites me especially as I enter into my forties.

I’ll end with this: all of us are a work in progress. If we don’t acknowledge our blindspots, limits and opportunities, then we’ll never reach our full potential, see our visions come to life and have the impact we dream of. Doing the work to develop ourselves isn’t easy but the rewards are boundless.

If you’d like to learn more about The LCP, feel free to send me a message. I’d be honored to talk with you about my experience and how it could help you.

40 Lessons From 40 Years

I turn forty today. I can’t even believe I just typed that sentence. Over the past month, I've been reflecting on the lessons I’ve learned directly through experience or indirectly from family, friends, mentors and teachers.

I wanted capture and share these learnings for one important reason: I’m now a father to a beautiful baby girl and I’m not going to be here forever. Preserving myself digitally is becoming more important as I enter middle age.

Here are forty nuggets of wisdom that I’ve picked up throughout my first forty trips around the sun. May the next forty (god willing) be as wonderful and enlightening as the first forty.

  1. It’s ok to say, “I don’t know” because it’s impossible to have all the answers. The older I get the more I realize knowledge is practically infinite and I don’t know that much.

  2. Don’t underestimate the power of being the first to truly believe in someone.

  3. Everything rises and passes. It’s a law of nature. Change is constant around us and within us.

  4. Don’t always trust your feelings and snap judgements about others. We’re very good at crafting stories and beliefs in our minds with very little information and context.

  5. Every person is likely struggling with something. Be kind. Be helpful.

  6. Don’t buy something just to buy it. Accumulation of things will never lead to sustained happiness.

  7. When we speak openly about our challenges it can give others the strength and courage to do the same.

  8. Time is the single most important non-renewable resource we all have. Fill your days with what truly brings you alive, fills you with energy and allows you to grow.

  9. The only person you can change is yourself. It is nearly impossible to change other people. However, when they notice your own change, it might give them the courage or impetus to change themselves.

  10. Being a parent is 5x harder but 100x more enjoyable and fulfilling than I ever imagined. Love for a child is boundless. Caring for your child is the purpose of life.

  11. If you want to make progress on the things that matter most, you need to decide who you’re going to disappoint. It’s inevitable.

  12. Real trust and deep relationships can’t be manufactured or rushed. These are built over time through countless authentic and meaningful interactions and experiences.

  13. Traveling is single most effective way to learn about yourself, humanity and the world.

  14. Most of the time, family and friends don’t need you to fix their problems, they just need you to be there with them.

  15. We are all far more powerful, resilient and adaptive than we even realize. It’s never too late to change and remake yourself. We are all a work in progress.

  16. Equanimity isn’t suppression of thoughts or feelings but rather being ok with how a situation unfolds or how we feel in a given moment.

  17. Meditation is surest path to understanding yourself, your feelings, your thoughts and your perceptions.

  18. If you wait for the perfect moment or inspiration to learn a new craft or create something, you’ll never progress. Start now if it’s truly burning within you or else you’ll be exactly in the same place ten years from now.

  19. Listening with your eyes is just as powerful as listening with your ears.

  20. Living a sober life is vastly more enjoyable and liberating than society wants you to believe. You can have fun and be social without substances.

  21. Every single one of us has a different map of the world. So if you want to understand someone then you have to understand their map.

  22. Don’t force things. Apply the just right amount of effort but not too much.

  23. Being uncomfortable will take you to your edge and that’s where real growth and transformation happens.

  24. How you spend your time and your calendar reflects what you truly value in life.

  25. Pick your spots. We have limited time and our brains can only process so much. Focus is key. Choose wisely.

  26. A great teammate always puts the organization and its purpose ahead of their own self interests.

  27. Admit when you’re wrong and/or being an asshole. And when you are, learn from those experiences.

  28. You can’t be everything to everyone so might as well be yourself. Follow your values.

  29. All relationships, even the healthiest ones, are difficult and complex because most humans aren’t ‘compatible.’ The key to making them work is open communication, patience and compromise.

  30. You can likely learn the fundamentals any topic or craft if you dedicate ~100 hours. That’s not much time in the grand scheme of things. Immersion leads to progress.

  31. It’s not about the light at the end of the tunnel. It’s the tunnel. Show up every day and enjoy the process.

  32. Journaling for at least fifteen to thirty minutes is one of the most powerful forms of self care and therapy.

  33. You’ll never get what you don’t ask for or actively seek out. Go for it!

  34. Don’t expect to achieve very much if you spend your life trying to please others.

  35. Good physical and mental health is the single most valuable thing in the world. It starts with a good diet, regular exercise and ample sleep (7-8 hours).

  36. Long walks in nature are amazing for processing thoughts, emotions and important decisions.

  37. The best investment you can make is your own education. Never stop learning. The second best investment you can make is building your network through authentic and meaningful interactions. It is what you know and who you know.

  38. Sometimes you need to slow down to speed up or go backwards to move forward.

  39. Forgiving and making amends are brave and powerful acts that can help you turn the page and begin to move forward.

  40. Life isn’t perfect for everyone but we all have the freedom to choose how we respond to our circumstances. Don’t underestimate the power of faith, hope and positivity.

How Shake Shack Taught Me To Be A Better VC

One of the internal areas I focus on at Primary is what we call the ‘founder journey.’ This is the end-to-end experience that a founder has with Primary. It includes everything from the initial intro email all the way through post investment support. As a startup, we strive to be thoughtful about every touchpoint and interaction. We’re far from perfect and refined but working hard to improve every single day.

At the firm’s annual offsite this summer, I presented an update on our ‘founder journey’ progress and the strategy for the next twelve months. I kicked off the presentation with a quote from Danny Meyer.

“Business, like life, is all about how you make people feel. It’s that simple, and it’s that hard.”

For those who know me well, know that I’m a huge fan of Danny and his company Union Square Hospitality. Danny has created some of the best restaurants in New York including Union Square Cafe, Gramercy Tavern, Eleven Madison Park and Shake Shack.

For many reasons, I believe venture firms are in the hospitality business. This is something that I try to preach internally. In a hyper competitive, cash flush environment, entrepreneurs are likely to go with the firm that gives them the best shot to succeed and the partners they would like to work with over many years. At the end of the day, we’re in a people driven services business.

On the way back from our offsite with hospitality on my mind, I pulled out my Kindle and re-downloaded ‘Setting the Table’, Danny’s memoir and philosophy on business. This is one of the best books on leadership and hospitality that has ever been written. I’m not kidding. It’s so good that I’ve read it multiple times over the years.

Danny’s central philosophy is ‘enlightened hospitality,’ which is how the delivery of a product or service makes its recipient feel. He makes a compelling argument that hospitality is the key differentiating factor for success in a service-driven economy.

Because we now live in an information rich world, the knowledge and barriers required to launch a product and service have collapsed. This is why we’re seeing multiple competitors emerge in just about every category from CPG to SaaS. It feels like every product or service is being commoditized including the venture capital business. In this kind of environment, the difference maker is the internal culture of the organization and end-to-end customer experience.

So how does an organization move from just shipping a product or service to fully embracing enlightened hospitality? It begins by defining, understanding and prioritizing your core stakeholders.

Who do you exist to serve? Who directly benefits from your organization? Which relationships do you prioritize? Why? What implications do these choices have on your strategy and decision making? How do you satisfy and balance the interests of each group? What can you do differently to serve each of them more effectively?

Stakeholders should be different for just about every organization. An obvious example: our stakeholders at Primary are certainly different than those of The City of New York. And for good reason. This is driven by leadership, strategy, sector, values, purpose, culture, philosophy and so on.

In the case of Union Square Hospitality, the organization has five primary stakeholders “to whom we express our most caring hospitality, and in whom we take the greatest interest.” How the organization prioritizes these stakeholders is the guiding principle for every decision they make. According to Danny, this approach has “made the single greatest contribution to ongoing success of our company”

Their stakeholders in order of importance are:

  1. Employees

  2. Guests (a.k.a. diners)

  3. Community

  4. Suppliers

  5. Investors

Danny fundamentally believes that unless he prioritizes and takes care of his top four stakeholders then he won’t be able to take care of his investors and provide them with a strong and long-term return on their capital:

“To prioritize differently breaks the virtuous cycle of enlightened hospitality and seriously compromises the chances that your business will achieve excellence, success, good will and soul. Prioritizing our way has enabled us to offer investors an opportunity to affiliate with a business known for outstanding employees, warm hospitality, strong ties with exceptional supplies and a solid commitment to playing an active, valuable role in its community.”

When you deliver value to each of your stakeholders, it creates a flywheel effect (or virtuous cycle) and positions your organization for long term success and sustainability. Getting this flywheel humming is much easier said than done. For starters, every stakeholder group is different and has unique interests. Additionally, the world is always changing so you have to adapt your approach over time. Finally, these decisions and tradeoffs permeate throughout every function of an organization.

If you’re a founder or leader within an organization, I challenge you to think about your key stakeholders and how you’re delivering both short-and-long-term value to them. Who are you serving? What is the value exchange? Where can you improve? What needs to change?

I’m asking these questions internally at Primary and to some of our portfolio companies. It’s a fun and important thought exercise.

In closing, delivering true value to all of your stakeholders requires a huge amount of buy in, effort, intention, time and money. It’s certainly complicated but it can be achieved as Union Square Hospitality and other great organizations have proven. Doing this well might very well be the difference between building an enduring market leader rather than just an average company.

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 Turntable.fm, 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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