Nick Gray and I worked together in NYC. If you don’t know Nick, you should. Nick was described as a “modern day Emily Post” and that only scratches the surface. Nick is a twice-exited entrepreneur and investor who spends most of his time running a small family office and writing a weekly newsletter which I think is one of the most interesting things on the internet. was his personal Chief-of-Staff during some of the big growth years of Museum Hack. Nick had just handed over the reins as CEO to the extraordinary Tasia Duske and was figuring out what the next professional chapter of his life would look like. We worked together to look at investments, supercharge bringing value to his network (a big priority if you know Nick at all) and most of all plan cool parties with awesome people. Everything from small cocktail parties to a large birthday party at Lincoln Center, of course with nametags.
Nick is also very much stuck in my head thanks to the quote below
"What idiot did this!?" is almost always, "A smart, well-intentioned person making tradeoffs you hadn't even considered.” [Great reminder from @nickgraynews]
— Alexis Tryon (@AlexisTryon) January 24, 2018
Nick Gray and Cocktail Parties
Nick has a VERY specific way of hosting a party. I’ve seen it, dozens of times. There are name tags, and icebreakers, and party reminder messages, and lots more. My favorite part about the parties was always how many new connections were made. My job was to help run all of the logistics to make them seamless. At our height, we were hosting one party per week.
This is a new book from Nick that will launch on June 14, 2022. He sent me an advance copy, and I’ve read various versions of the book over the past few years. I know it will be great.
This is a whole site that Nick made about how to host a party, with various tips, tricks, techniques, shopping lists, etc. See more at www.party.pro, and here are links to some of my favorite articles there:
- How to Host a Party in a Small Apartment
- Party Reminder Messages: The 3 You MUST Send
- Guest Bios: My Secret Weapon (I’ve seen Nick use these, they work SO WELL!)
How to Make New Friends
Nick says that the best way to make new friends or build your network is to learn how to host a happy hour or a cocktail party. The book talks a lot about that. It is an extremely tactical book.
I’m super happy for Nick to finally get his book out. I learned so much from working with him and a good chunk of my networking game is inspired by the way Nick operates. I hope others can benefit from his unique way of hosting. It can be easy! But of course, it also helps if you have a great Chief-of-Staff named Mike.
Let me know if you buy the book, would love to hear what you’ve learned.
All other things are never equal.
Anyone who has taken basic economics understands the theoretical tradeoffs between supply and demand. As the Add Slider price goes down, demand goes up. As the price goes up, demand goes down; ceteris paribus, which means “all other things being equal.” The problem is that, in the real world, the other factors are never as equal as theories like this suggest!
Ceteris paribus also assumes you can go out and survey every potential option in the market to find the best price. Most of the time in life, that is improbable if not impossible; especially when you factor in sun, opportunity, and switching costs.
A few examples…..
In a perfect world, you could see every single home available in the area and take your sweet time figuring out where to rent or buy. But that’s not how it works. At best, you are seeing 3-6 months of inventory and likely only a few weeks based on what’s available and the depth of your search period.
The average home buyer sees 10 homes. Let’s take a cosmopolitan area like Queens, NY, where there are around 10,000 homes sold each year. That means ~5,000 homes are available in a 6 month search period. Breaking down further to neighborhoods let’s say the consideration set is 500 homes. That means 10 homes is only 2% of the available inventory. This is absolutely no way you can effectively survey the entire market.
We are in the midst of the Great Resignation, and talent is moving faster than I have ever seen in my career. Similarly to house hunting, the idea of the market implies that we could survey every single employer interested in our talents, get a thumbs up thumbs down, evaluate the finalists and pick the one that fits you best. I have searched multiple times in my career and coached dozens of folks; I can say that is a pipe dream. Company A wants to move fast, but Company B wants to move slow. Company C gives you an offer but needs to know precisely one week before Company D, your dream employer, gives you your first interview. The incentive is for an employer to lock you up quickly so someone else can’t have access to you. A few years ago, when I was on the hunt, I had two offers in hand in the middle of the month, but an interview with a dream employer wasn’t till the 31st.
I was able to kick the decision point by a few weeks and eventually didn’t proceed with the dream employer. Had things moved forward, I would have had to accept one of the options on the table without having enough time to evaluate all potential options. According to my friend and career coach extraordinaire Ryan Dickerson, applicants with solid referrals, LinkedIn profiles, and resumes can expect to see roughly a 10% response rate.
“Let’s say that you land the 5th job you were selected to interview for. By then, you will have proactively applied to 50 appropriately suited positions, and you will have networked with 50-150 connections/recruiters/talent acquisition professionals along the way,” he told me.
Simply put, with timing and building a pipeline, it is impossible to accurately survey the entire bevy of options at your professional fingertips.
I am happily in a long-term committed relationship but remember the stress and trauma of dating. The dating market is arguably the hardest thing to solve as it is intimately tied to our emotions. Since we are all unique snowflakes, there is not much of a baseline to compare individuals beyond how they make you feel. You can emotionally detach yourself from work or your home. Despite stoic philosophy being all the rage these days separating yourself from a romantic relationship feels like entry-level psychopathy.
According to the census, approximately half of US adults are single. With ~19M people in the NYC metro area, that leaves 9M, single folks. Given I was searching for a jew and a woman, 2.4% and 50% respectively, that puts the total market at 108,000 individuals. I set my apps to 25-35 rage, which is 12.5% of the population which gets the final number to 13,500 women in my target market.
I was pretty intentional and proactive about dating and felt like I had about two dates a month for a decade. To find my partner, I only sifted through less than 2% of the available “supply.”
TLDR: for the essential things in your life, you are often viewing a fraction of a fraction of the total options available, which makes selection hard primarily due to a lack of complete market visibility.
What to do about it
As I go deeper into my 30s, I think one of the more complicated challenges in life is making decisions with incomplete and often imperfect information. Jeff Bezos is known for trying to make decisions with 70% information, and Reid Hoffman likes to aim for 80% if it means moving fast, so, in my mind, 75% is a great place to be.
Wait any longer and you risk hitting analysis paralysis or making a decision too late. That said, approximating percentages is easier said than done, so it helps to have heuristics to help you through the process. A few of my favorites…..
When money is involved, it’s a little easier to do the math for the options on our plate. Economics tells us to fall back on expected value which at its most basic form is multiplying the upside by the odds of getting it. For dating, it’s impossible to calculate in these terms. For buying houses, it’s still difficult. But with salaries, it is pretty straightforward.
Two job searches ago it came down two finalists. I don’t think anything is ever 100% certain in life, so for Applico, the consulting opportunity, I gave it a 90% chance.
The calculation was a little more complicated when it came to the political campaign. In September 2019, Andrew Yang was one of 8 or so remaining candidates. With a general election a year away, the job was, at best, a one-year gig. So to account for that, it likely was a job and not a career; I dropped the 12.5% to 10%. Even though I was unquestionably more passionate about the Yang campaign than consulting, I knew the math made no sense for me to take the job.
Four months after this, Andrew Yang suspended his campaign, which meant that had I accepted the job I would have only earned about $8,000 and then would have to start the entire job search machine all over again.
Downside awareness is the most accessible lens to look at risk through. Risk doesn’t always have to be avoided, but, at a minimum, it should be part of the decision-making process. With things like housing, dating, and employment the downside is usually pretty tame with losing some money or going on a bad date. The downside comes into play more with health-related concerns.
This year and last, I’ve been reading and writing in The Daily Stoic Journal. One of the big messages it preaches is to think about the downside and realize how it isn’t actually that bad. What is my current downside? I lose my job, I burn through my savings, and if somehow after a few years and I haven’t made a dollar I have to go hat in hand to my family and friends asking for support. Sure, it may be embarrassing or emasculating, but with no health consequences, it won’t kill me, and just realizing that gives me a sense of peace.
Play the tape to the end
I really value long-term thinking and get frustrated with short-term orientations. If you’ve worked with me you’ve probably heard me say “play the tape to the end” which means to take the thing you are focused on and look a week, month, and a year forward and explain how it plays out.
You buy the apartment in queens, so it stands to reason you’ll be living a Queens-centered life in the coming years. You take the job in consulting and your career path then orients mostly around consulting.
I find a surprising amount of people making short-term decisions without considering the long-term outcomes. Often this is referred to as “second-order consequences” and I find it to be helpful to remember this when evaluating the big things in life.
My 20’s were all about entrepreneurship. I earned not one but two degrees specifically in the discipline and then went on to raise money and build product for a startup I cofounded. I’ve always been interested in this corner of the business world but I often think the wrong lens is applied for new ventures.
The narrative we hear is that the lightbulb goes off for a world-changing idea like Instagram and then you lock yourself in a garage for months at a time and just build. Inherently, this is doing something that’s never been done before, so there is a massive learning curve associated with something new.
Instead of doing something that’s never been done before, some of the smart entrepreneurs I know and admire are looking at what they already have on hand as a foundation for creation. This is known as effectuation.
Effectuation is predicated on leveraging what you own or know or have access to when starting something new. You already have the home, the laptop, and other foundational assets. By using what is already in your pocket or brain to get started the barrier to entry is almost nonexistent, which gets you in business sooner and lets you get near-immediate feedback from the market.
Almost everything can be tested. A date is a test for marriage or for a long-term partnership. An interview is a test for a job. There are very few things in this world that can’t be broken down into smaller digestible parts. We buy something at the bodega before committing to buying a 100 pack at Costco yet we don’t move this lens to more important things in life.
You can test drive the car before you buy it and maybe spending a night in a home before you buy is hard but certainly not impossible. Jobs are an often overlooked area where testing can make a huge difference.
This is admittedly harder at larger companies but pilot projects, like my friends at Laskie describe, are a great way to test the waters before making a life-changing decision like employment.
Through Many Lenses
I’ve found that just having any process for making important decisions matters more than which lens you choose to look through. You have to be intentional with big decisions, especially when there is no formulaic way to process them. They often have farther-reaching implications than you can tell on the surface; yet, you often need to execute without slipping into “analysis paralysis.”
If you’re used to making decisions without a framework or are stuck with a single lens, try picking one of these up the next time. Even just writing these down makes me feel better about having a process for important decisions. Am I missing any important lenses? Let me know in the comments.
I want to narrow my focus this quarter
I’m scheduled for surgery this quarter and it is certainly going to slow me down both physically and metaphorically. Thankfully I have the ability to take medical leave at work which makes me feel incredibly fortunate. I’ve been known to take things too fast and I want to give myself ample time to recover. This will likely mean weeks away from a computer screen and a slow down to most of the things I am chasing. If I don’t dedicate time to this recovery this will continue to nag me. No real metric to track other than do i feel better than I currently do on Jan 1st.
- Recap: What a whirlwind. Definitely feel better than I did October 1 but somehow am still dealing with the dumpster fire that is paying medical bills. Here’s a thread of my surgery and recovery experience. Super grateful that I had my girlfriend, roommate and parents help me as I was an invalid for a week or so. Also what a blessing from EY that I was able to go on short-term leave and focus on recovery; I genuinely did not receive a single message about anything work related during my time out. That says a lot about the firm. I would say at this moment in time I am 85-90% recovered as I still have aches and pains and scarring but I am mostly on the right path and back to my normal life.
Last quarter I made a spreadsheet of habits I wanted to track and i totally abandoned it. Despite nobody reading this blog I think publishing the spreadsheet held me back a bit. I want to track things like meditation, tracking food, journaling and a few other things but gonna keep the tracking effort private.
- Recap: I did this for a few days and then surgery took me off my routine which I am going to make a focus point for 2022 Q1
- Views from Roosevelt Island + six month anniversary
- Airbnb in Catskills with friends
- Christmas picnic and seeing Marc Maron perform
- Two friendsgivings
- Cousins wedding
Favorite companies and market opportunities
Each of the past three years as an emerging investor I’ve published a post on the companies I would include in my portfolio; assuming they would take my money and reasonable deal terms.
This year I’m adding a new component: opportunities I want to fund which will be gaps I see in the market at the time of writing
Update on previous companies
Three companies were acquired: ROIKOI, ClearFactr, and WeFind. Unclear terms but likely some level of liquidity. Density and GoPuff raised mega-rounds and are both the talk of the startup town.
Lambda Scool is a well-capitalized pioneer and leader in their market and by many accounts the defining company of the category. Upgraded was acquired by Ticketmaster and Udelv is partnering with Walmart
All are alive and kicking but still in relatively nascent stages.
A company with an asterisk means I am either an investor in or have worked with as a consultant.
Avenify is a marketplace lending platform for Income Share Agreements
Higher education is very much broken. The main underpinning of the issue is a flimsy funding model that requires a tremendous amount of debt or a mid-six-figure price tag to get to a completed degree. What I find most ridiculous is that there is a huge disconnect or lack of alignment between the success of an individual, most notably the job they earn upon graduation, and the institution. Excluding future donations, the school has no financially vested interest in the success of students after they have been paid. If the graduate works for minimum wage or multi-million dollar salary the school as a business is paid the same. This is where income share agreements or ISAs provide novel value. The school and the student are aligned towards an outcome that is mutually beneficial. Avenify is building a marketplace for ISAs with an initial wedge focused on nursing schools.
The New Standard in Print-On-Demand
Dreamship runs a print on demand network which serves as a back office of sorts for many builders of physical goods. One of the struggles of being a small business especially producing physical products in small volumes at early stages is the pricing is horrific. You can’t get pricing that makes your business competitive with more established firms. Dreamship helps shortcut much of this headache by giving creators access to production facilities and supply chains previously unimaginable. Essentially it lets the smaller upstart businesses get to market faster and compete in a global marketplace more efficiently. I got to know the founding team in the fall and am excited by their growth.
The value of management consulting delivered through software, playbooks and a network of experts.
I’ve spent a large chunk of the past few years in management consulting and know this space is ripe for disruption. Much of the industry is competing in a highly regulated space like audit, assurance, tax and other services that by definition have to follow standards like Generally Accepted Accounting Principles (GAAP). This means the services essentially become commodities with little differentiation across players. The last area for competition ends up being what can broadly be called “innovation” which includes M&A, spinoffs, spinouts, corporate innovation and anything else dealing with disruption and new business models. This is why we are seeing offerings like BCGDV, Capgemini Invent and similar value propositions coming from the big consulting firms. These engagements are solid seven to eight figures and only accessible by Fortune 500 size firms. This is where software comes in and can provide value for businesses who ordinarily couldn’t access this type of service. Laskie creates assessments that help firms leverage improvements in strategy, process and or delivery of service without incurring the expensive person-hours of traditional consultants. I’ve been fortunate to work with the Laskie team on a few of their initiatives.
Founders: You’re owed $50K by the IRS. We’ll get it back for you in 20 minutes, no paperwork required. Free to qualify.
If you are old enough you may remember Matthew Lesko, the guy in the question mark suits who made commercials selling books that helped people apply to government programs like grants that would fund investment or education. There are billions of dollars available from governments and nonprofits that go unclaimed each year. These are particularly important for businesses to leverage given they are essentially free. The problem is accessing these funds usually takes complicated forms and outdated processes to access. Mainstreet modernizes this process to make it easier for founders and executives to get crucial capital to fund their businesses.
Use social posts as currency at select online stores.
We are roughly 15 years into social media and we are only starting to see the link between commerce and social networking. Influencer marketing is here to stay but to this point it has mostly been a one-way street. Influencer posts about the product after being paid by the brand for the exposure or gets a cut of the sales. Swaypay flips the model on its head and lets people pay for their products by sharing the purchase to social media. While a few steps away from cash it is a relatively inexpensive way for a retailer to buy exposure without increasing their ad spend. I think swaypay will be acquired, or strongly imitated by a Shopify type company or similar eCommerce solution
Ideas, concepts, and blue oceans I am interested in. If you know of anyone working on something like this please let me know
Intellectual supply chain
We are now nearing a year of nearly the entire business world working in a remote manner due to the covid-19 pandemic and remote work is here to stay. One of the unfortunately consequences of remote world is the inability to poke someone on the shoulder and as such a misalignment of operations. Sure you can call, text, slack, email, whatsapp etc but everyone has a different operating procedure so miscommunication can happen at scale in a remote environment. This brings an opportunity for what I see as project management 2.0 or a supply chain of business process work products. Asana, Trello et. al are great for one off task management but they really lack features for teams. Think of a client presentation that is due on the 30th of the month. That means a rough draft needs to be completed by say the 25th with 26-29 left aside for revisions. This requires rigorous alignment across the team’s remote processes. Everyone has a different work flow and work hours and newer tools will take these into account.
The calendar in its modern form has not changed much in the last 20+ years. Sure the desk calendar has been digitized but in 2020 it is essentially the same as it was in 1990. Calendars can run your personal and professional lives but mostly lack intelligence. As a calendar devotee I would love to get insights from how effective I am with my calendaring. What meetings run long? What are my most productive times? There are a myriad of insights waiting to be unearthed. A challenge here is logging each activity. Logging every minute of your day takes a ton of work which is why I see a larger opportunity with passive tracking efforts like RescueTime. Some might find that invasive but I propose it only is viewed as invasive it if doesn’t yield value. For example here is my year in review from RescueTime. Cool data but limited insights. I want an analytics system that improves how I operate. Microsoft is dipping a toe in the water with MyAnalytics and a startup called Reclaim has a similar value proposition.
One of the things I have noticed in corporate America is there is a tremendous instance of the prisoner’s dilemma; situations where coordination would be mutually beneficial but fails to happen. By that, I mean at nearly every company I have worked at or consulted with there is a layer of feedback that management does not give to workers and workers do not give to management due to misaligned incentives or fear of firing. I feel anonymity can be a powerful tool here but there needs to be some function that eliminates gossip or avoids retribution and only relevant feedback is produced. For example, take tools like StatusHero. Very powerful in theory but often folks are hesitant to put the most pertinent feedback into writing. Software can be a great way to mitigate this problem. A few months ago I created a one pager of the offering and tried to build a service around it. I still believe this is a blue ocean.
For the last few months, I’ve been job searching and want to make it as easy as possible for friends and contacts to help me. That means more work on my end which I happy to take on but often there are barriers vis a vis my access to a friend’s network. For example, searching through a friend’s network is somewhat limited. I can’t only see a slice of who is connected to whom and asking a friend puts more work on their shoulder which is the opposite of the goal. I would like to see a way where can delegate our social networks to very close friends for discrete purposes. In this scenario I can more easily search through a friends network without making a huge ask on their part. In addition, this concept works while sharing or disseminating information. I love helping my friends, especially entrepreneurs. I would gladly give someone access to my social feeds to share messages that would benefit them. Of course this would only be for my inner VIP circle but I see an opportunity here. This is much easier than being constantly asked to share or RT things. I tweeted a little more about that here.
Similar to the issues with calendaring, the inbox remains mostly unchanged since the dawn of the internet. I’ve been a user of mailtester for a number of years but it doesn’t give me actionable ways to improve my inbox management. Here is my monthly email report from October 2020. I’d gladly pay for a service that improves my email workflows. Helps me spend less time here or learn where I am not responding appropriately or efficiently. There was a great startup called Conspire that published a monthly report for each of its users. You can see my report from a few years back here. They were acquired by FullContact but the product was deprecated.
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