What’s Next For Telehealth

It’s been an eventful past few years for Telehealth (to put it lightly). Telehealth usage started at less than 1% of outpatient visits pre-COVID, shot up to 13% percent in the first six months of the pandemic, and has since fallen back down to ~8%. With both COVID and telehealth usage numbers flattening, there has been a lot of conversation about the future and direction of telehealth moving forward. So what comes next?

There’s a striking range in what people think when they think “telehealth.” To many, their experience with it has been as a 1:1 replacement. They’ve had the same appointments with the same providers. However, instead of those being in-person, they’ve happened over video.

Given that, it is no surprise that telehealth visit usage numbers look the way they do. To these patients, telehealth visits quickly went from a non-option, to the only option, to a choice. Many providers now offer both in-person and virtual visit options, and will continue to do so. More choice is good for patients, but those visits remain a virtual copy of what they have traditionally been.

Telehealth goes from good too great when it stops copying and starts stealing. Telehealth truly succeeds when it takes the good parts of provider visits, but blends them with capabilities that would be impossible without technology. For example, new care models can utilize smart device data, asynchronous communication, and automated interactive educational content (often alongside shorter provider video visits), to deliver care that goes far beyond what could be possible in-person.

“Automated”, “interactive”, “asynchronous”, and “smart” all sound like buzzwords, but this new type of care is happening. Both startups and large incumbents are launching and scaling care models that are fundamentally different than what could be offered in-person.  The issues these new care models address (addiction, asthma, chronic pain, obesity, etc), and the type of care they provide, are all very different. However, these care models are unified by the common thread of tech-enabled recurring healthcare. Also excitingly, many of these new offerings are proactive. By more effectively addressing patient issues before they require urgent care clinics or hospitals, these models could fundamentally shift the type of care our healthcare system provides.

Before video games, there were mechanical pinball machines. You can (and people do) make video games that copy pinball machines. However, the best video games aren’t pinball machines copies, and we don’t sit here and talk about what percentage of pinball games are played mechanically versus virtually.

The above sounds a little absurd, but that is where the telehealth discussion is right now! Telehealth replacing traditional in-person medical visits 1:1 is a tiny part of the potential benefits.  Telehealth’s future should be forecasted based on the new types of care that it allows for.

That future is bright.


Stripe turns 10 today, so I figured I’d share my favorite personal Stripe story. It’s an experience that greatly impacted how I think about customer service (and growth) at Healthie. It was Jan 2013. I had recently turned 16, and was building my first product that I wanted to charge people for.

I’m not sure how I found Stripe (probably through a coding tutorial) but decided to use them to add subscriptions to the product. I was (to put it nicely) raw at programming, and had never built something like that. I got stuck for a few hours on adding coupon codes to the checkout. I thought I was experiencing a bug with Stripe and fired off a support email.

Shortly after, I realized that the issue was completely on my end, fixed it, and moved on, forgetting about my support ticket. Later that day, Stripe Support followed up to confirm I had gotten it resolved, and offered to send me a free t-shirt. A shirt? For free?! Sounds tiny now, but at the time I was over the moon.

I was a high-schooler. I hadn’t taken any payments through Stripe. I didn’t even have access in Stripe to run real credit cards, and they were going to mail clothing across the country to me. Sure enough, a few weeks later the shirt (along with stickers and a handwritten card) arrived.

Getting that shirt was one of the first times I felt like I could be a real part of the startup ecosystem. It felt like a badge of honor. I wore it in the airport the first time I went to SF. I wore it around Palo Alto the first time I went to Silicon Valley. I wore it for years and years until it gradually ended up full of holes and unwearable. It made me, an awkward teenager, feel like I belonged.

The product I was building didn’t work out, nor did the next few, but the admiration and respect I had for Stripe never went away. Three years later, when we started Healthie, it was never in doubt what payment processor we would use.

We’ve since processed over one hundred million in payments using Stripe, and have paid them millions in fees. Shipping that t-shirt, which probably cost them $20, ended up being a pretty decent investment.

It is (relatively) easy to provide personable support to your largest customers. It is hard to do the same for your smallest. However, those tiny customers normally appreciate it a lot more. It feels more unique and special to them, and can give you life-long advocates.

Surgery and Startups

When I had my second open heart surgery in March 2017, the thing I worried about most wasn’t the getting anesthetized and cracked open during the surgery itself, or the mortality risk, or the uncertain recovery. it was the impact that being unreachable for a couple days would have on my startup.

In the lead up to my surgery, Healthie was a year old. We’d raised a million dollars just a few months prior. When you raise, you paint a vision for investors, full of billion-dollar liquidity events and company immortality. You paint a picture of being able to predict and control the future. Going under for surgery is the opposite of all of that. You are giving up all control (and consciousness). You are placing your life and future in the hands of a surgeon you’ve met a couple times and in a care team who are complete and total strangers. It sucks.

It was hard for me to tell my cofounder about it. It was mortifying for me to go from raising money, to our next monthly board meeting, where I felt obligated to tell our new board member (and also lead investor) about my newly scheduled surgery.

I was worried that they’d think I wasn’t pulling my weight, that I wouldn’t deliver on my promises due to a medical event I had no control over. I was concerned about how all my recent direct hires, who I pushed to bring on, and had agreed to manage and lead, would do in my absence. I thought I’d be letting all our customers down, especially the many who I had gotten on sales or success calls with and promised that I’d be there to offer personal support.

In all these cases, I’d stammer out a poor explanation about having a problem with my aortic valve, and that I’d need to be out a few days for a surgery. I’d prep myself for the worst responses, and get nothing but understanding and positive reactions. It wasn’t even accommodating or sympathetic (which I appreciated), just people being supportive and treating it as a non-issue.

I was knocked out for the surgery itself, and the immediate recovery is full of blurry memories and dialudid. A day later, after recovering enough, I felt unnecessarily compelled to hop back on email and support tickets from my phone in my hospital bed. This was a bad idea.

A couple of days later doing that, my recovery was progressing well and I was hours from being released. I got an automated email alert that we were having web application availability problems. My blood pressure spiked so much that an alarm went off, and a nurse came rushing in.

The alert ended up being a non-issue, and my blood pressure went back to normal. However the blood pressure spike (despite my explanation) greatly worried my care team, and I came close to not being released from the hospital that day.

In hindsight, I took one of the worst things ever to happen to me, and made it worse. Despite my worries about having surgery, our customers didn’t mind, my cofounder didn’t mind, our investors didn’t mind, and our team performed admirably in my absence. I took a shitty, scary time and made it shittier and scarier.

It’s common to talk about a reality distortion field that comes from a startup’s founders. However, I’ve never seen anyone taking about that field distorting things in reverse. As a founder, you’re supposed to live and breath what your company does. That attachment makes it very easy for founders to overemphasize and fixate on molehills, which quickly turn into personal mountains, and in many cases (including mine), actual quantifiable health issues.

In hindsight, my reaction was incredibly irrational. However, as a founder, it’s normal to seem irrational. The ability to have strongly differing opinions is what allows founders to build big, novel companies. Unfortunately, that same personal conviction can cause trouble.  I know it did for me in this case.

If you’re a founder beating yourself up about personal events that are outside your control, take a deep breath. What’s inflicting more damage to your company? Those events? Or your reaction to them?


For the first time in over a year, I’m resting my elbows on the carved wooden bar at the hole in the wall, only in NYC dive bar underneath our (now former) office.

Undercover cops shot a black security guard on the doorstep in 2000, after the security guard refused to sell them pot. The Grand Jury declined to indict them. Anthony Bourdain,  the Hunter Thompson of our time, drank here. 30,000 New Yorkers have died of COVID since I’ve last sat at this bar.

This bar has five different names — on the sign, on google, inside, etc, including one calling it a “distinguished cocktail lounge.” I recommend buying only bottled beer and paying only in cash.

This bar is a survivor, between a LensCrafters and a Dos Toros. It’s one of three businesses on this block older than 10 years, the others being a hardware store, and a sex shop that has a sign proclaiming its “busines hours.” (sic)

This bar is a survivor, but in between the (mostly) socially distanced bar seats, are ghosts. Of Bourdain, of Patrick Dorismond, the father of two murdered by undercover, unidentified cops, of the 30,000+ New Yorkers killed by “just the flu.”

Much like scars, the ghosts never go away, but they make us who we are as a city. On dark, rainy nights like this, where we can uneasily re-experience something we took for granted for so long, I remember them.

Survival Bias in Startup Advice

Lots of startup advice is told like a war story. Founders of (now) successful, thriving companies talk about the dark days, full of all nighters, personal debt, stalled growth, and low runway.

These war stories generally include advice like “never quit” and “keep on pushing.” The storytellers talk about taking huge personal risks, working themselves to the bone, and approaching their mental breaking point.

These stories all have the same ending. The efforts paid off, the company turned around, and the founders did (more than) well. They look at these dark days almost nostalgically, and talk about how they overcame them on Twitter or over drinks.

These stories all have happy endings because the companies (and their founders) survived. Very few people look to advice and stories from unsuccessful founders of failed companies.

Companies that ultimately fail have plenty of dark days as well. Their founders, in many cases, work just as hard and take on just as much personal risk as founders of companies that work out. However, their stories end in a range of begrudging acceptance to soul-crushing sadness. It’s not pretty.

3 years ago, in April 2018, we went through one of our darkest days at Healthie. Our sales and marketing strategy was not working, and we had to lay off 20 people (85% of the company) in a single day. What followed was three months of little sleep and crunching the team, trying to rebuild our product from basically the ground up. It was an absolutely miserable time, but ended up turning our company around, and put us on a sustainable path to fast growth, profitability, and success.

We survived those dark days, but a lot of companies don’t. There were times where it looked like we wouldn’t, and I still have mixed feelings about how close myself and other employees came to burning out. Our decisions were the right ones, but I definitely made them with a great deal of naive optimism.

If you’re struggling and thinking about the best path forward, it’s important to be mindful of survivorship bias in startup advice. Before taking on immense risk and emotional burden, get a clearer picture of your expected outcome, not just stories told through rose-tinted glasses.

Entrepreneur is a Dirty Word

When I meet new people, and explain Healthie and what I do there, some of the most common responses are “It must be cool to be an entrepreneur” or “I want to be an entrepreneur.” I always smile, nod, and cringe internally.

I am not an entrepreneur. I build healthcare software.  No one is an entrepreneur. Despite literally millions of LinkedIn profiles with that title listed, “entrepreneur” is so generic and non-descriptive, that it ceases to be a real thing. You can be the founder of a specific business. You can even be a “serial founder” if you really want to call yourself that.  Those words describe actual actions taken.  “To Found” is a verb. “To Entrepreneur” is an absurdity.

When asked about your job/career, You would never say that you are a “business person” or a “human.” Calling yourself an “entrepreneur” is equally as generic and unhelpful. Worse, the word “entrepreneur” has been latched on to and weaponized by the Grant Cardone, Kevin Zhang, fake Lambo-owning, get-rich-quick-course-selling crowd. They talk about their glamorous lives as “entrepreneurs” and use the concept to take advantage of people.

They can only do this successfully because so many legitimate people currently call themselves “entrepreneurs.” When I searched the job title “Entrepreneur” on LinkedIn, many of the results are people who have built real businesses, who have created amazing products and teams. These are people that I respect, look up to, and want to emulate as we build Healthie. Frankly, the fact that they refer to themselves as “entrepreneurs” undersells their achievements.

We should be using words and titles that focus on specific actions taken and work completed. The more we do that, the easier it becomes to recognize and celebrate builders, while leaving scammers and charlatans behind. Let’s stop using the word entrepreneur.

Finding a Developer for your MVP

The most common question new founders ask me is how to hire developers to help build their MVP. These founders are normally passionate and knowledgeable, but are not technical. Their companies (like most nascent start ups) are normally tight on cash and time.

In an ideal world, these potential founders would all have a trusted technical friend who had the time, willingness, and ability to help build an MVP. In a slightly less ideal world, new founders could go to a meet up, hit it off with a person who is a great initial fit, and have them build it. Unfortunately, both these scenarios are rare. Good developers are in high demand, dev jobs are well paid and stable, and new startups are risky and painful (albeit hopefully rewarding). This leaves a tiny pool of developers that fit the above two categories.

New founders can’t afford to wait for the perfect developer to come along. To get the ball rolling quickly and affordably, these founders normally need to look to a much bigger pool of talent, namely online freelancers.

What follows are the tips and learnings I’ve gained from hiring contractors at Healthie, as well as helping a bunch of brand new companies find their first engineers. 

The below advice is for you, assuming you’re a non-technical (or not technical enough) founder building a web or mobile application with minimal tech risk. For example If the MVP of your app is based around machine learning or has intensive graphical needs like custom 3D rendering, there is likely better advice out there. This advice also assumes you’ve exhausted preferable options like finding a developer who is a great fit and you know directly (or comes highly recommended as a referral).

First, three pieces of general advice on hiring and working with your first engineer hire. 


  1. References, references, references – no matter who you hire, you should always do reference checks. No one is offended by it, and talking to references really helps you work with the hire. In the case of good references, they help you learn how the hire likes to work and interact with others. On the downside, the hire can’t provide references (or the references are lukewarm or negative) and you can avoid a huge amount of trouble. The worst candidates we hired at Healthie looked amazing on paper and from their initial interviews. We were very excited, and didn’t want to risk losing them, so we made offers without doing reference checks. In hindsight, references would have exposed the issues that we had to learn very painfully. 
  2. Own your accounts – You should be the primary account holder/admin on all services that your engineering hires are using to work with you. Most notably, this includes where your code is stored (e.g Github), where your server is hosted (e.g AWS), and the tool you use to manage the project (Trello or Clubhouse). Your first engineering hire may have (strong) opinions on the specific tools to use. Whatever tools you use, you need to be the one to create the account, and then invite the engineer as a user. This has a range of benefits, but most importantly, it protects you and your company if your relationship with the engineer ends badly. It makes you much less vulnerable to a bad first hire, which unfortunately, does happen. 
  3. If you’re non technical, avoid making technical assumptions. When it comes to development, some seemingly complex things are trivial, and some seemingly trivial things can be incredibly time-intensive to add. It is important for you to trust your developer, to respect their estimated degrees of difficulty, and to not micromanage. That said, it is worth doing the work upfront to feel very good about your engineering hire. It can also be helpful to have an outside technical resource that you can bounce basic assumptions off of (e.g does two weeks to build out a graphing dashboard make sense?)

With those pieces of advice in mind, it’s time to find the engineers to build your MVP. I normally see founders look at five main sources — agencies, Toptal, Upwork, AngelList, and Fiver. 

 I’ll go through them one by one, but first, here’s a TL;DR summary. You should use 

  • an agency if money is of no concern, 
  • Toptal if you have time, (less) money, and few tech skills
  • Upwork if you are comfortable taking a risk, very cost-conscious, or able to thoroughly vet candidates. 
  • AngelList along with Upwork (it’s more focused on full-time employees and with a smaller talent pool)
  • Fiverr never


Full service agencies promise the world, and sometimes, they deliver it. They normally pitch an approach where you give them the project details, and they can handle everything from design to tech specs to development to QA to release. Working with an agency is generally more opaque, hands-off, and expensive than trying to work with developer(s) directly.  That management layer needs to be paid for somehow, and they are, through the prices you pay the agency. They also generally charge high upfront project deposits that can be cost-prohibitive for new companies. 

When their work turns out good, it is high-quality, cohesive, and takes some serious weight off your shoulders. When it doesn’t, you can be left high and dry midway through a project. In my experience, you really get what you pay for with agencies. If the price sounds too good to be true, it is. 


Compared to the free-for-all nature of the other platforms, Toptal is a guided tour to finding a freelancer. You start using their service by getting on a call with a “matcher.” You explain the project and what you are looking for, and the “matcher” introduces you to potential fits that have already been interviewed and vetted by Toptal. You then get to interview the different suggested candidates yourself, and if you want, hire one. This approach has serious pros and cons. 

On the plus side, you completely avoid a lot of the outright scams and fraud that can be prevalent amongst online freelancer sites. If you are non-technical, you can feel comfortable knowing that Toptal has done both personality and technical interviews, and the candidate is who they say they are. I’ve worked with a lot of great  freelancers from Toptal, and the average quality is the highest of all freelancer platforms I’ve used.

However, Toptal does have large drawbacks. First, you are basically at the mercy of your “matcher.” I have seen cases where the matcher doesn’t set up many introductions, or is slow to respond. Other times, the matcher doesn’t have a good understanding of your project (or the project is badly explained to them), and you’ll be introduced to candidates that are clearly not a fit. This can be frustrating, and outside of badgering your matcher, you don’t have meaningful direct control over the speed or quality of matches. Finally, this extra layer of vetting and staff need to be paid for, and that is reflected in the general higher rates that Toptal freelancers charge. From my experience, freelancers on Toptal are not meaningfully cheaper than devs in New York. 


Decades old and formed by mergers of large freelance platforms, Upwork is the largest freelancer marketplace out there. It is a marketplace that covers every type of skill and experience level. Every job posting you make will be quickly inundated with applications. However, Upwork does close to no verification of it’s candidates. It’s basically a wild, wild west where you’ll find amazing developers for great prices, fraudulent but convincing charlatans, and everything in between. With Toptal, the difficulty is finding candidates. With Upwork, the hard part is sifting through them.

For some ”fun” anecdotes, we’ve had Upwork candidates switch out people between interview rounds, switch out people between the interview and the first day of work, and secretly take multiple full-time jobs and farm out work to lower paid devs. I have also been asked to give references on Upwork candidates who I have never heard of. It turned out there’s a whole series of fake portfolio websites out there that have added Healthie as work experience. Despite all those above stories, we still use Upwork! Why? If you can separate all the noise out, there are some fantastic freelancers on Upwork. If you are comfortable and capable of doing the vetting, and ok with some risk, Upwork has the best price to value freelancers that I have found. 

Here are some tips that have made a big difference to our usage of Upwork.

  • Have your application require specific questions to be answered. Try to make the questions specific enough to your project that candidates cannot just copy and paste answers. These questions lower the number of total applicants, show that the candidate put some initial effort in, and make it much easier to choose who you want to interview. In other situations, a longer application can deter good candidates, but that will never be an issue with Upwork. 
  • Be very selective about who you interview. Your big cut of candidates should come between the application and the first round interview. Otherwise, you will spend way too much time on video calls with clear non-fits. 
  • Require video to be turned on for all interview rounds. I like taking calls without video personally, but this is an important verification step
  • In the interview, make sure the person’s description of their experience and work timeline matches what was in the Upwork application. 
  • Take a screenshot of the person you interview, and at every round of the interview. Make sure that the picture matches anything online (e.g LinkedIn), and also that it is the same person at different interview rounds. This sounds insane, but candidate swapping (e.g a different person interviews than applied, or different people do different interview rounds) happens regularly. 
  • Ask for references, but don’t stop there. You want to do due diligence on the reference, both to ensure that a) the reference company is real b) the person you speak to actually works at the company. Candidates will provide fake work experience, and even fake references. If possible, you want to speak to a technical person at the reference company. 
  • If you move forward with the hire, hold them to a high initial standard of a) joining a daily check-in on time, and b) joining with video on and giving their update. This helps cut down on the farming-out-work problem, and you can be a lot more lenient once you get comfortable with the dev. 


AngelList is similar to Upwork. Anyone can join AngelList, and they do not vet candidates for you. Compared to Upwork, AngelList is more full-time focused, and is more U.S-centric. In general, it takes minimal extra time to post the same job on Upwork and AngelList, and there is no harm in doing so. 


Fiverr can work well for odd-jobs (e.g freshening up the design of a pitch deck), but your MVP is not an odd-job. Personally, I’ve had bad results with even trivial non-programming projects I’ve tried to use it for. It’s not a fit for this. 

Predictions for 2021

2020 is (thankfully) over. With the new year starting, now is the time to review my 2020 predictions, and add some new ones. This year, I’m going to avoid specific stock prices (since I can’t tie back underlying rationales to exact prices), and political races (since I’m burnt out on politics at this point).

Stopping reckless securities trading will become a cause célèbre, leading to self-regulation.

With a booming stock market, and an incredibly low barrier to entry, general excitement around securities trading (stocks, options, etc) has reached a fever pitch. Robinhood has been leading the charge here, offering a commission-free, user-friendly, and gamified experience.  Robinhood makes it easy to trade stocks, but also to trade options, and trade on margin. Many of Robinhood’s features are good (e.g fractional shares), but they also put Robinhood (and the industry as a whole) on the edge of PR disasters caused by users who are dangerously in over their head. These PR crises are magnified by issues with the apps themselves, leading to ultimate tragedies like this one. Over the next year, enough of these issues will accumulate, leading to greater self-regulation from the apps.

Prediction: In the face of consistent, widespread public outrage, Robinhood (and similar apps) will self-regulate, increasing their requirements to trade options and trade on margin.

Miami, as a tech capital, will be a short-lived Twitter fad. There won’t be a new tech capital.

If Twitter trends are to be believed, San Francisco is falling to pieces, and Miami is rising to take its place. VCs and founders are moving there, and throwing their weight behind it. The mayor of Miami has become a cheerleader (and meme), pledging support and cafecitos to all.  COVID (and issues with SF) will surely lead to Miami having a larger tech scene than before. However, the increase (especially in raw numbers of jobs) will be a rounding error, and not more than other mid-sized American cities like Austin, Seattle, Philadelphia, etc. In this new remote-first world, it is easy for individual people (like the VCs and founders who hype Miami on Twitter) to move. It is not easy, nor beneficial, for employers to ask all employees to. Large, established tech behemoths will remain in their current cities, Stanford is not going anywhere, and the Miami weather will sound a lot worse come summer. This all leads to a whimper, not a bang.

Prediction: By August, we’ll be talking about Miami, the same way we talk about Seattle or Philly. Miami will not see a meaningful increase in tech jobs, or VC investments into companies founded in Miami.

It will become common for startups to incubate in-person, and grow remotely.

Remote work sounds great, and, in most cases, is great. We are big fans of it at Healthie. It has allowed us to scale our team much more easily, and gives our employees (and us as founders) a great deal of flexibility. However, I still think it is very hard to get a company off the ground in a fully remote setting. In those nascent stages, iterations need to happen faster, situations change rapidly, and targets can be less straight-forward and measurable. Effective remote working requires a great deal of written communication, and process overhead. This additional structure is great for established companies with clear next steps, but is just extra baggage for companies in the pre-product and pre-revenue stage.

Prediction: A new model will emerge with founders and early employees working in-person together for the first three to six months of the business. After that period, companies will transition to being remote first.

Traditional IPOs will get less and less popular, as more companies opt for direct listings and SPACs. 

This has been a very interesting year for taking companies public. We’ve seen three major trends this year. First, traditional IPOs have continued to have large first-day “pops”, leading to companies leaving a lot of money on the table when they go public. This is not new. However, in 2020, new alternatives have finally begun to gain real traction, which brings us to the two other trends. SPACs hit the mainstream this year. These “reverse-mergers” allow companies to go public with the least amount of moving parts. Instead of a drawn-out traditional road show, private companies can work with a single SPAC. This simplified process has benefits for both the SPAC and the private company, and we will continue to see it used in cases where the company wants to go public early (Hims, OpenDoor) and/or is in a “sexy” industry (Nikola, DraftKings, or Virgin Galactic). On the other end, recent SEC approvals , have expanded the utility of direct listings, making it a better option for more companies.

Prediction: Q3 and Q4 will see well-known tech companies opt for alternatives to a traditional IPO. If Stripe goes public this year, it will be via a direct listing.

The U.S will get their vaccination act together

The U.S vaccination effort is off to rough start. Despite months to prepare, the country has been caught flat-footed, and progress is slow. It is jealousy inducing to watch Israel, a country with a population the size of New Jersey, be on track to reach herd immunity in just a couple of months. The U.S predicament is pretty close to cat herding, with fifty different states, a federal government in transition, and a president with his mind on other matters. However, despite our slow start, the situation will stabilize, allowing America’s resources to be put to good use.

Prediction: After a couple of months of non-stop media coverage of vaccination delays, the system will get into gear, and we will reach herd immunity by the fall.

Goals for 2021


Get Healthie to (redacted)MM in ARR

We had a strong year in 2020, and are looking to improve on that in 2021. I am confident that the opportunities and plans we tee’d up in 2020 will get us there in the new year.

Maintain Healthie’s profitability in 2021

As I mentioned last year, being a (cash-flow) profitable company lets us control our destiny, and build the company we want to build. Now that we have a history of turning a profit, we should maintain that, barring any large new growth channels that prove worth pouring a ton of money upfront in to.

Make API product a meaningful part of Healthie’s business

In order to enable our own practice management software (and its features like scheduling, video chat, payments, etc), we have had to build some very cool back end tech in-house. In 2021, we want to to make that available to other companies as an API product. A lot of work has already been done. Goal is to launch in January, and reach (redacted) in MRR by the end of 2021.

Write and share my thoughts more regularly

In 2020, I started blogging somewhat actively, publishing 13 posts (versus 0 in 2019). I also was quoted in a couple of third-party articles, and tweeter more frequently. I want to build on that by publishing two blog posts a month, and tweeting more, with a goal of 100 newsletter sign-ups (up from 9), and 1000 Twitter followers (up from 180)


Work out 4 times a week

This is a carry-over goal from 2020. I failed miserably. Easy to blame on COVID, but, with greater self-control, is definitely something I could have accomplished. When I work out regularly, I sleep and manage stress better, and it’s definitely something I want to make a focus in 2021.

Learn to Surf

One of the benefits of COVID is that I don’t have to be in NYC in the office all year. In 2021, I want to go somewhere with good surfing for beginners, and become a competent surfer.


Read 45 books

I didn’t read a single book in 2020 until mid-April. After that, I got back into gear (thanks eBooks!) and read 31 (mostly great) books before the end of 2020. I want to keep up the consistency, and read 45 books in 2021. I read almost all non-fiction, but feel free to send any type of recommendation.

Complete a full week of New York Times crossword puzzles in a row

Crossword puzzles have been one of my consistent quarantine habits in 2020, and I’ve gotten a lot better at them. Currently, I can complete Monday through Wednesday close to 100% of the time, but struggle beyond that.  In 2021, I want to complete 7 puzzles in a row (e. Sun-Sat). I’ll count any 7 subsequent days, so the streak can start on any day of the week.

 Call/meet with 1 new person a week (outside of job, immediate family, and my SO)

Especially with COVID (but even before), it is easy for me to get tunnel vision socially. I regularly get on calls for work, and with my SO and immediate family. However, I don’t do a great job actually talking to (not just texting) the wonderful people outside of those groups. I want to get on a call (or meet up with if COVID allows) a least one new person a week. These people could be extended family, older friends, or just people I come across that seem interesting.




Just Ask

On a recent Hacker News post about Stripe pricing, one of the top comments was posted by the founder of Streak.

Streak is close to a decade old, has hundreds of thousands of users, and presumably millions in annual revenue. They went through Y Combinator, the same accelerator program as Stripe. Yet, despite all this, they have apparently been on Stripe’s out of the box rate for the past nine years. Stripe offers discounted volume pricing, and Streak almost certainly could have saved tens of thousands of dollars by taking advantage of that.

Why is Streak not on a lower-fee plan, despite their qualifications? They must never have asked. Stripe will happily give volume discounts, but they don’t do it automatically. You have to ask.

The simple act of asking has made a huge difference for me, both on a business and personal level. I didn’t use to ask. I used to assume that whatever was offered was the best option available. Outside of very specific situations where there is an explicit negotiation (buying a car, flea markets, etc), I didn’t think there was any wiggle room. Clearly, from the Streak cofounder’s experience, I was not alone. There are countless intelligent, driven people who accept most offerings as they are initially presented.

After starting Healthie, I realized that was absolutely not the case. This realization came from two major factors, seeing how customers acted with us, and watching my cofounder interact with others. With customers, despite any initial intent, I found customers who “asked” getting better service and pricing. If a customer asked, It made sense to me to knock a little bit off the price to get a deal in the door.  When going through support tickets, we responded faster to customers who followed up, or expressed urgency. This doesn’t mean that these customers had less ability to pay, or had more important support requests, but they did better on both fronts then those who took everything as is.

My cofounder, Erica, is firmly in this vein. When we started Healthie, I was blown away by the type of things she would ask for. “Are you sure you don’t have any extra tables?” when a restaurant said they had a thirty minute wait, or “is there anything more you can do on the price” after a vendor had already given us their “best price possible.” I felt somewhat awkward being around her during these requests. It felt cheap, and borderline unprofessional.

Despite how I initially felt, the vendor clearly didn’t feel that way about Erica. We would get a table early, or get an additional discount, and Erica’s ask wouldn’t be held against us. Instead, I felt like we were respected, and treated more fairly off the bat in our future interactions with the same vendor. I was amazed. There was a whole host of opportunities that I had never even realized. I just had to ask.

There are definitely limits to asking. You need to be firm, but always respectful, and ask in good faith. You should benefit from what you are asking for, don’t just ask to see if you can get a concession. Also, don’t ask about everything. It very rarely makes sense to have a 30 minute call to save $10 for your business. That said, if you aren’t asking regularly, you are doing a disservice to yourself, your company, and your colleagues. Just ask.