Schlaf.me

Several weeks ago, I was introduced to a talented young man who, like me, is passionate about personal growth and technology. He has been developing a new system grounded in research to help people drive change in their lives personally and professionally.

Before our video call, I visited his website, twitter feed and his other online profiles, only to discover he has not shared much over the years. I could not see what interests him, what he thinks about, and what he values.

While we were talking, I thought to myself, ‘This young man has so much knowledge to share with the world and could help others yet he isn’t using any digital tools to distribute and amplify his work.’ I wondered why this was the case so decided to ask him.

His response was short and simple: “I haven’t found my voice.”

This hit me hard because voice is expression, voice is communication, voice is creation, voice is confidence and voice is power.

Over the last few weeks, the phrase, “I haven’t found my voice” has been echoing in my head. I believe this young man wants to share his ideas badly but there is something getting in his way. He is not alone. There are thousands of people out there who want and deserve to be heard. Once I realized this, I began to ask myself, how does one find his or her voice?

I have been reflecting on that question for the past week. Here is what came up for me based on my experience and a number of conversations with friends.

1. Believe in yourself just enough to get started: when we start anything, whether it is riding a bike or recording a podcast, the initial step is often the hardest because we feel awkward and might not have command of the skill or craft. Ignore your inner critic that is trying to hold you back. Believe in yourself and just start.
2. View your work as practice: Every essay you write, every class you teach, every workshop you facilitate, every picture you take, every video you record, every podcast you broadcast is practice. Practice, practice, practice. You can always start over tomorrow. Creation is a practice.
3. The medium matters: Select a medium that excites you, challenges you, fits into your routine, feels native to you, and allows you to fully express yourself. Experiment. There are a range of online mediums: Twitter. Instagram. Snap. Medium. WordPress. Podcasts. YouTube. And remember you don’t need to find your voice online. You might be more comfortable conversing, teaching and facilitating in person. That’s ok! Go for it. Remember, not everyone is born to thrive on every medium but we all have the means to test these mediums and discover which ones align with how we want to communicate with the world and share our ideas.
4. Listen to your inner voice, not your inner critic: Your inner voice often knows exactly what wants to emerge but too often our inner critic gets in the way. If you are inspired to use your voice and create something, give that voice more weight than the other one telling that you’re too busy, not good enough or don’t know what you’re doing. Follow the inspiration.
5. Be patient and persistent: Finding your voice will take time. People work hard to find their voices and hone their craft. This doesn’t happen over night. And you will likely not feel comfortable at any step in the process. Here’s the good news: if you invest a 15–30 minutes each day, the results will follow. You will create momentum. I have no doubt.
6. Be genuine: This one is critical. Don’t emulate someone else. Be yourself. Develop your own tone. Follow your values. Follow your interests. Follow what you truly care about. If you honor who are, what matters to you and what you are truly passionate about, your voice will be distinct and it will show.
7. Don’t compare: If you are recording an interview series, do not compare yourself to Larry King. If you are writing a short story, do not compare yourself to Stephen King. If you are starting a blog, do not compare yourself to Fred Wilson. If you are starting a vlog, do not compare yourself to Casey Neistat. You get the point. Instead, focus on your voice, output and weekly small improvements.

This all is easier said than done. I struggle with writing even though I want to express myself through this medium. I definitely have not invested as much time as I would like but I am trying. In fact, I recently blocked out time on my calendar each week to write. Additionally, I badly want to publish a podcast on leadership but I have not taken the first step. I am aware of this which is the first victory. Creating and finding our voices certainly is not easy but I know it is possible if we invest the time and make it a priority.

I will end with this. It does not matter if you have an audience of one (you!) or an audience of a million. There are people out there waiting to hear (and see) your message. Being heard and seen is a fundamental human desire. Remember that. Follow your inner voice and heart. Speak up. Share. Ignore your inner critic. Let the world see and hear you. We all have something to say and contribute. Now go find and hone your voice. Good luck!

I’m thrilled to announce that I’m joining Primary Venture Partners as a Venture Partner. Over the last six years, Ben and Brad have been co-investors, thought partners and friends. Ever since the fall, they have been helping me think through a number of paths I have been exploring. That discussion evolved over many months, to the point where it became clear that we had a lot to gain from each other. This started as a super casual, “Hey, why don’t you come hang out for a while,” thing and evolved from there to the point where we realized it made sense to combine forces.

Ben, Brad and the rest of the Primary team are arguably building the most hands-on and operationally minded Seed fund in NYC. They do not spray and pray. They are active, high-conviction lead investors, and they care deeply. They are also focused exclusively on NYC, which was a huge factor in my decision. Everyone at the firm deeply believes in this ecosystem, and that is reflected not only in their strategy but also in how they are building the firm. Most importantly, everyone around the table has operational chops, strong values and a real desire to help NYC founders build impactful companies.

As I have peeled back the curtain and talked with founders in the portfolio, I have been blown away by the Primary platform. The firm’s Portfolio Impact Team, comprised of dedicated Talent, Finance, Market Development and Communications pros, is designed to support companies from whiteboard all the way to Series A and beyond. Additionally, the Primary Expert Network, a network of over 200 seasoned technology operators and functional experts, helps founders solve their most pressing tactical problems. They’re just getting started, too. Many firms these days claim they have a platform, but it’s often just “checking the box.” Not Primary. They’re investing aggressively and playing the long game to build a real franchise here in NYC.

Many people have asked me, “So what is a Venture Partner?” The title means different things at different firms. Here’s what I’ll be focused on: My first mandate is to find and partner with amazing founders building companies here in NYC. I’m amped to get back into the investment game after a brief hiatus. My second mandate is to help the firm with overall strategy. Over the last decade, I’ve been fortunate to work at some amazing firms and learn from many incredible investors and founders. I’m going to share lessons learned and potentially help operationalize some new programs. The third mandate is to support the existing portfolio with ad hoc executive coaching. I’m currently enrolled in an intensive transformational/executive coaching program, and I look forward to deepening my practice with the Primary family. Finally, I’ll have some freedom, space and time to explore a range of longer-term projects and paths.

Monday is my first day at Primary and I couldn’t be more excited to get started. If you are a founder or operator in NYC and are looking for advice, capital and/or executive coaching, my email is steve@primary.vc. Drop me a note to say hello. I would love to support you on your journey.

Raising money from VCs is an important step in the company building process. It marks the beginning of a long-term relationship that can last longer than a decade. In my experience investing in and advising countless founders, company building is not rainbows, unicorns and lollipops. Startups are filled with adversity, challenge and struggle. That’s why it’s critical to find the right investors who are going to support you when times are good and have your back when the shit hits the fan. It likely will at some point on your journey.

Fundraising should be viewed as a two-way dialogue. Each side should interview the other. While I understand and appreciate the desire and pressure to quickly raise and get back to work, taking enough time to really get to know your partners is a good investment of time and effort. This goes for both sides. If the VC you’re meeting with doesn’t want to spend the time or directly answer your questions, that should be a telling sign. Going into any long-term partnership with eyes wide open is just a smart strategy. Remember, all relationships are complicated. The healthiest ones are built on shared values, open communication and mutual respect. That’s why it’s worth spending the time upfront and understanding who your investors are before they write the check.

So how do you cut through the VCs sales pitch and really get to know the investors during the fundraising process? It starts with asking thoughtful and targeted questions. Be curious. Your objective throughout the process shouldn’t be to interrogate and incriminate but rather to find the right fit and long-term partner(s) for your business. Go for a walk with them. Grab a meal or a coffee. Really get to know them.

If you’re unsure what to ask or what is in bounds, you’re in luck! I’ve created a fairly exhaustive questionnaire that you can reference while you’re on the fundraising trail. Most of the questions are relevant if you’re talking to an institutional VC while some might not be if you’re talking with angels. Know your audience. I recommend doing some research and trying to answer as many as you can before the meeting so you can focus on the most important ones. You won’t have much time so choose carefully.

I hope you find this to be a useful resource before or while you’re on the fundraising trail. Remember, don’t settle or rush the process even if you have ample options. Having the right investor, who is not only a good fit but also will have your back, can be a difference maker. Godspeed!

The Juicy Ones

What makes you uncomfortable about our company? What do you like?

Who in your partnership is going to push back? What are they going to say?

How do we fit your investment thesis and / or align with your worldview?

On a scale from 1–10, how good do you feel about our company right now? Why?

Where are your blind spots with respect to our opportunity?

Can you name a time you stood up for your company in the face of opposition from your partners or other investors?

How have you / the firm handled companies that have underperformed relative to expectations? Can you share some examples?

How would your founders describe you when you weren’t in the room?

Do you engage or disengage when things get difficult?

How do you handle the pressure?

About The Fund

Can you tell me a bit more about Acme Capital and your current fund?

How many partners do you have? Are they generalists or sector-specific experts?

What is your ideal stage?

What is your average check size and do you reserve for follow-on investments?

Do you lead and take board seats?

How does your firm define a “core” investment? Would we fit into that camp?

What are your return expectations?

How large is your current fund and how many more investments do you have left to make?

How does the firm think about bridge rounds or extensions?

Do you have any category or geographic limitations?

What are the last three investments your firm closed and what got you and the partnership excited?

Who are some of your favorite and frequent co-investors?

How can the firm help us build the syndicate for our next round?

The Partner / Investor

What experience or perspectives do you have that are relevant to our company?

What’s your superpower?

What are your core values?

Why did you become an investor?

How many board are you on? How much time do you have for each company on a monthly basis?

Have you ever fired a CEO? What happened?

How long does it take for us to schedule a meeting and / or get on a call?

Do you believe in the partner or the platform?

How would your founders describe you?

What’s your style (hands-on, data-driven, etc.)

What are two or three examples of how you’ve added value to your portfolio in the last month?

Investment Process

Are you running point or will someone else take the baton?

Can you describe your investment process in detail?

Do you have the authority to lead investments or do you work with a partner?

How does the firm make decisions?

How will I know where I am in the process?

On average, how long does the process take from first meeting to close?

Portfolio

What are some lessons you’ve learned from your portfolio that you could apply to our company?

Which companies in your portfolio could we learn from?

Who in founders or operators in your portfolio would be good for us to know?

Do you have any conflicting or tangential companies?

Support

How do you think you could help us?

What’s the firm’s philosophy and strategy on support?

How have you supported companies like ours?

Do I get you and/or the firm? Can you explain?

How do you work with your companies?

Last week, I bumped into a buddy who runs a fairly large venture-backed company. I asked him how things were going. Rather than getting the common response, “everything is great,” he explained that he had spent the last few quarters developing a new product only to discover the customer response has been lukewarm. He said this experience stung because countless hours and hundreds of thousands of dollars were spent building the product. He had also used up significant political capital with his Board. He asked me what I thought. I simply replied, “Don’t let the sunk costs get in the way of deciding what’s best for the business.”

A sunk cost is a cost that has already been incurred and cannot be recovered. We all experience sunk costs in our personal and professional lives. They can include money spent, time, effort and energy. Sunk costs play a big role in startups and investing. Startups and investors are faced with a barrage of sunk costs on a regular basis:

• Spending huge sums of money to develop a product only to discover there isn’t a market for it
• Hiring a key executive only to discover he or she isn’t a fit
• Making a big promotion only to realize the employee isn’t set up for success
• Naming your company and buying a domain only to find another company has the trademark
• Launching a large advertising campaign that doesn’t produce results
• Hiring expensive recruiters or consultants that don’t deliver
• Investing in a company that doesn’t perform relative to expectations

A lesson I learned in school and throughout my career: valuing and harping on sunk costs often leads to poor decisions. It is human nature to try to salvage an investment of time, money, energy and effort. Avoid the trap. They are counterproductive when making forward-looking decisions. They are often an illusion. Don’t let them get in the way. Treat the money, time, energy and effort as gone forever. I realize moving on can be painful and feel barbaric but it can also be liberating.

Whenever sunk costs are influencing decisions, I always recommend coming back to this question: ‘what’s best for the company going forward?’

As an investor, this often presents a dilemma. Investment theory suggests that any incremental dollar invested in a company should be evaluated separately from the initial check. I typically subscribe to this principle. It is sound and responsible. But what happens if a company is in a tight spot and needs additional investment to get to that next critical milestone or achieve an outcome? Is declining an investment in this situation truly in the best interest of the firm? I would argue that most often it’s not.

Venture, especially seed investing, is a human-driven and long-term business. My reputation is all I really have. If I don’t step up in times of need, I’ll eventually develop a bad reputation and founders won’t want to work with me. Being a supporter in tough times is not only the right thing to do from a human and karmic perspective but I also believe it will result in better returns over the long run.

Dealing with sunk costs isn’t so black and white after all. There are grey areas that ultimately challenge our values. If you just focus on what’s best for the company in the long-term you can’t go wrong.

(My dad this summer in Woodstock, NY)

I recently read an excellent essay by Andrew Kortina titled, “They Say the #1 Killer of Old People is Retirement.” In this piece, he discusses the importance of finding purpose and meaning deep into life. Andrew outlines a confluence of factors that are causing mental and financial hardships for baby boomers. Many are struggling emotionally and financially for a variety of reasons including lack of savings, meaningful work and intellectual stimulation. He proposed several interesting solutions based on this simple idea: “I think we can help people continue to feel productive and valued by instilling them with some sense of greater purpose after retirement.” Kortina’s post conjured thoughts and feelings about my father who recently turned seventy-five.

Several years ago, dad was in a tough spot mentally. He had aged out of the workforce and just experienced his second divorce. Additionally, he was living alone for the first time in nearly thirty years. While he had some savings and a predictable income stream from Social Security and an annuity he purchased, this cushion likely wouldn’t be enough if god-forbid there was an emergency or if he is lucky to live beyond his mid-eighties. During this period, my dad would run errands, go to the gym, watch sports and hang around the house on most days. That was his routine. My siblings and I could tell he was depressed, lonely, hopeless and stuck in a vicious cycle.

My dad’s situation isn’t unique. There are more than 70.4 million baby boomers in America according to the U.S. Census Bureau. Workforce participation among boomers is on the decline. Nearly half of boomers haven’t saved for retirement and sixty percent are relying heavily upon Social Security to be their safety net (link). Furthermore, one in seven boomers is treated for depression, which is a higher rate among other generations of American adults (link). Finally, divorce among Boomers is increasing. The number of divorces among that age demo has doubled since the 1990s (link). When looking at the various data points, it turns out that my father isn’t an outlier.

One day last year, I was having a heart-to-heart with my father. We were trying to brainstorm hobbies, odd jobs, volunteer opportunities and local organizations where he could spend his time and perhaps earn a few bucks. I suggested joining the local senior center. That idea didn’t resonate because he still felt young and couldn’t identify with being a senior. We talked about him becoming an usher at Fenway Park since he loves the Red Sox. That likely couldn’t work given the night games and the forty-five minute commute to and from Boston. He suggested working at a friend’s restaurant as a host but they’re only open for dinner. My brothers and sisters also got involved and suggested a bunch of ideas but none seemed to stick.

I felt like we were at a dead end until one afternoon when I was talking with my father about his situation. For some reason in that moment, Viktor Frankl and his seminal book, ‘Man’s Search for Meaning,’ suddenly came to mind. The book chronicles Frankl’s experiences in the Auschwitz concentration camp during World War II, and describes his psychotherapeutic method, Logotherapy, which is founded on the belief that human nature is motivated by the search for a life purpose. Fulfillment achieved through pursuit of meaning in one’s life. Frankl famously wrote, “Everything can be taken from a man but one thing: the last of the human freedoms — to choose one’s attitude in any given set of circumstances, to choose one’s own way.” In that moment, I said to my dad, “You need to find something that will give you purpose and meaning in life.”

Several weeks later, I got a call from him and he sounded upbeat. He proudly announced that he was going to apply to be a substitute teacher in the local area. While my dad was a sales executive for most of his career, he has always had a passion for teaching, coaching and helping youth. I could tell he was excited about this potential opportunity and this could be the solution he and my family had been looking for. He approached the application and interview process as if he was going for a full-time job with a Fortune 500 company. He prepared for hours, gathered strong references and followed up after each of his interviews. He left no stone unturned. It wasn’t very long until he had a job as a substitute teacher in multiple school systems.

Today, my father is a full-time substitute teacher at Salem High School. He loves going to school every day and interacting with the students and the faculty. They challenge him (in a positive way) and help him remain young at heart. No job at the school is above him. He’d mop the floor if they asked him to. He’s contributing in his own way. He’s healthier physically and sharper mentally. He believes he’s making a difference. At age seventy-five, he has managed to find his calling in life. Isn’t that amazing? Most importantly, my dad has finally found meaning and purpose in life. I honestly haven’t seen him this happy and fulfilled in the last twenty years. Every few weeks, my dad will thank me for encouraging him to seek meaning and purpose. The nudge, while simple, was all he needed.

So why did I tell my dad’s story? I feel it’s our generation’s responsibility to help our parents and elders find meaning and purpose should they need a compass. They paved the way for us and now we’re standing on their shoulders. There’s so much we can learn from them. There’s a good chance that we’ll want the same support and guidance from future generations. Helping boomers find a new north star might be one of the biggest untapped opportunities that not enough smart people are focused on. Sure, there might be economic upside in cracking this nut, but I feel there are far larger benefits: less-depression, more quality time with loved ones, better relationships, more independence, healthier bodies and minds, and hopefully longer lives. That seems like a no-brainer to me.