Everything I knew about stretching was wrong

In the past 12 months my body’s mobility and flexibility went from abysmal, a source of persistent pain impacting my quality of life, to pretty darn good. I’m not about to become a stretching influencer, but after a year of researching, trial and error, and hard work I feel back on track and like I have tools that will really serve me and my body for decades. I’m honestly grateful for the big wake up call and I thought I would I share the most important things I learned.

A year ago my 37 year old body was completely wrecked. It snuck up on me. In the pandemic I started seriously strength training for the first time. I spent two years lifting heavy 3-4 days per week and it worked. I gained 20 pounds of muscle. For the first time in my life I got really strong, bench pressing my bodyweight and deadlifting/squatting around 2x that.

But throughout this process, I completely utterly neglected my flexibility and mobility. Rock climbing and yoga have been main exercise for most of my adult life, but climbing gyms and yoga studios were closed or inaccessible for most of those 2 years. So I packed on layers and layers of new muscle fibers with virtually no mobility work.

On top of that, I had the most stressful two years of my life on both personal and professional fronts. I always thought the idea that “we hold stress in our {body part}” was woo woo nonsense. It isn’t. Persistent stress and tension has a real affect on our bodies.

The problem is the typical weight lifting session doesn’t require a ton of full body mobility. The barbell that stabilizes the weight, allowing you to exert the most force possible, also limits the range of motion you actually utilize at the gym.

Without my noticing it my mobility fell off a cliff. My shoulders were frozen stiff. I couldn’t raise my arms over my head, hold a basic down dog, or touch my hand to my back or shoulder blades at all. I couldn’t touch my toes or even sit on the floor comfortably. Every major muscle group was hard as a rock all the time, as if I was flexing it as hard as I could. My range of motion was laughable and everything was gobbed up with layers of fascia.

Then I started trying to use my body to do things again—rock climb, ski, bike, yoga, or just carry things up a 4th floor walk up—and my whole body imploded. First, everything felt unbelievably challenging because every single body movement felt like it was pulling against heavy resistance bands. Next, everything hurt all the time. I had persistent muscle soreness, tightness, and pain all the time. Then the last straw was the nerve pain. I started getting numbness in my fingers and periodic electric shocks of pain going up both my arms doing simple day to day things like opening a door or picking up a cooking pan.

It sucked. I felt like I was 90 years old, decrepit and in constant pain. It was seriously degrading my quality of life and I was willing to try anything and everything. So here’s what I did:

  • I went for a massage 2x/week
  • I bought a fancy Theragun massage tool
  • I went to two different local physical therapists
  • I started going to yoga 2x/week
  • I start stretching and warming up before climbing workouts

3 months of all of that did exactly nothing for my mobility issues.

Massages and percussive massage tools can provide some temporary relief but have no lasting effect.

Sorry, but it seems that most PTs have absolutely no idea how to systematically treat these kind of issues. Like a massage therapist, they would use a kind of scraping tool or some other treatment that would provide some relief, and tell me to do nerve glides, charge me $250, and tell me they’d see me next week. But the process didn’t seem to have much of a real methodology and each week felt like zero progress. My experience seems to be similar to that of many others dealing with similar issues.

Yoga and pre-workout stretching are fine for maintaining flexibility, but not barely effective at creating flexibility, especially when you are severely limited.

The turning point

As I have often done in my life when the conventional solutions to a problem are failing me, I turned to the Twitter community for help and also went deep down YouTube and other internet rabbit holes. And that’s how I learned that everything I thought I knew about stretching was wrong.

The turning point was when I got connected to and did a virtual consult with Sam Martin from Move Better Project (huge thanks to Sam Segar for making that intro). Sam explained to me that the numbess and nerve pain was likely Thoracic Outlet Syndrome or something similar where my stiff gunked up inflexible muscles were compressing and trapping the median nerve that runs from the shoulder through the arm and down to the fingers.

Sam gave me a bunch of simple exercises to target each muscle group (including some hard to find ones). But he also gave me a radically better overall understanding of how stretching and mobility actually works. These fundamental ideas explained why none of the stuff I’d tried before had any real effect and laid the groundwork for me to effectively build an approach to my own mobility.

I realized that I was a bit of an extreme case. Interventions that worked for most people, felt like they barely made a dent in my issues. That’s when I discovered a number of great YouTube channels dedicated to mobility for power lifters and other beefcakes. These guys were preaching similar methods as Sam, but devising more intense variations that I needed to unlock by extremely laminated muscle fibers.

I’ll share some specific examples below, but here are the main ideas I learned that completely changed my approach to mobility.

What I learned

Hold stretches for 2 minutes (or more!). The kind of brief stretching you might do in a vinyasa yoga class poses or while warming up for a workout will have almost no effect on increasing your flexibility. To move the needle on your flexibility you need to be holding each position for at least two minutes, and sometimes more like 5+ minutes. Yes, this takes a long time. For several months while I was rebuilding my mobility I was spending 30-45 minutes almost every day on mobility.

These long holds, initially needing up to 5 minutes each, were the key to getting my shoulder mobility back into a good range.

The good news is that, at least in my experience, this only necessary when you’re trying to increase your mobility. Once you get things in a pretty good place, shorter regular stretching will do a good job of maintaining.

Smash it, don’t rub it. Rubbing your muscles mainly just increases bloodflow, which is nice, but isn’t going to break up the years of fascia and adhesions or release chronically stiff muscles. You need to smash them instead.

  1. Create pressure in the meaty part of the muscle with something like a lacrosse ball. For me I usually have to move it around until I find a particularly stiff (and painful) spot to place it.
  2. Once you find the spot, DON’T MOVE THE BALL AROUND. Keep it in that same spot and hold that pressure for ~2 minutes or until you feel like the muscle release. For me this can feel like a long time where nothing is happening except this ball is painfully jabbing into my muscles, and then out of nowhere the muscles just melt all at once. Stay in the same place until you feel that change happen.
  3. To increase the intensity and get even more relief, keep the pressure point in the same place, but start moving the muscle or limbs around it through their normal range of motion while still holding the pressure point in the same place. To understand what i mean, watch Sam in this tricep smash video and how he moves his whole arm while keeping the ball in place.

This smashing technique was the essential ingredient in finally releasing extreme tightness I developed in my pecs, from bench press-type exercises, and in my shoulder blades, from a severe muscle imbalance. More on that below.

Train your nervous system, don’t just stretch. It’s easy to think of your muscles as just some kind of rubber band and flexibility is just a matter of mechanically stretching them out so they get looser. But that’s not how it works. Most of the time your body is already physically capable of achieving the position, but you need to train your nervous system that it’s safe for it to relax into that position. So it’s not very productive to just contort your body, grit your teeth and sweat for two minutes while trying to watch TV. You will definitely get some benefit from this, but the far better approach is to consciously focus on steady breathing and mindfully relaxing the muscles one by one.

This kind of mindful breath-focused stretching has been essential for my lower body hip and hamstring mobility in particular.

Persistent tightness is as much a strength issue as a flexibility one. If you’ve figured out how to smash a muscle and stretch it and it still keeps getting tight, it’s probably a strength imbalance issue. Other muscles around it may be overdeveloped and are essentially pulling it out of balance all the time. This will feel a little counter-productive, because strength training a muscle will often make it feel tighter in the short term. But over the long-term a combination of smashing, stretching, and strengthening is often the right balance.

Mobility tools that actually work

I was in so much pain that I bought every mobility gizmo I could find. My home workout area looked like a medieval torture chamber. Most of those things are gathering dust now. Here is the short list of, mostly very cheap, mobility tools that actually work:

  • Lacrosse ball: this is your go to smashing tool.
  • Psoas tool: This is the nuclear option for smashing. It’s designed to target deep muscles like the psoas but I also found it incredibly helpful for releasing muscles in my shoulders and back.
  • Resistance bands: I used these both for building strength to correct imbalances and as a way to stretch my shoulders. I’d get a pack like this one with a door anchor unless you have something at home to anchor them to.
  • Yoga blocks: Great for support getting into positions where your flexibility is very limited like a split. Can also be used to increase the intensity of a stretch.
  • Giant yoga mat: I found it really helpful to have a large surface area to move through the positions I needed and this over-sized yoga mat was perfect.

Recommended Internet Rabbit Holes

Here are some of my favorite resources for learning more in general and finding specific suggestions for how to diagnose and target individual mobility issues.

Sam Martin, Move Better Project (YouTube): Sam’s YouTube page is filled with tons of great short videos for specific exercises. I also booked Sam for a virtual consultation which was one of the highest value things I did all year.

Smashwerx (YouTube): This was my favorite of the channels targeting more hardcore power lifters. In particular this video, involving dangling a kettlebell while you smash your pec into a bar, was the only thing I found that finally unglued my pec muscles.

Strength Side (YouTube): This is a fantastic all around strength and fitness channel and they have a bunch of good mobility routines, like this lower body one, to easily incorporate into your day to day.

Instagram: My two favorite follows right now are @kruseelite and @twstraining.

Lastly, despite all these resources, I never found a video of anything that could release the tightness in my shoulder blade that I just could not get rid of. I discovered this nuclear option muscle release using the psoas tool. Watch the video here.

 

Cooking For Founders

With COVID-19 forcing many of us indoors and cooking more (yes, this post took a little longer to go live than I planned), there’s never been a better time to really learn how to cook. I grew up not learning much about how to cook and taught myself as an adult. Over the last 5-7 years I went from someone who could do the absolute bare minimum (boil pasta, cook chicken breast, etc) to genuinely quite a decent cook. I can easily whip up dinner for 4-6 friends without stressing, cook healthy dinners at home most nights of the week, run a barbecue for 12 people, and have a small quiver of fancy dishes to impress friends, family, and my wife from time to time. This post is mostly about what works for me, but I’m calling it Cooking For Founders because I think it will resonate with a lot of entrepreneurs who think like me.

The goal of this post is not to teach you how to cook but to provide fairly comprehensive, but also minimum viable, roadmap for going from a cooking noob to solid home chef.

Why you should cook

Until I was about 25 or so I really didn’t cook much. I lived in places like NYC and London where restaurants were always open and ubiquitous and especially in these cities, it’s a perfectly reasonable position to just not bother learning to cook well. But I want to make the case that even if you have world class restaurants and food delivery services on demand, you should learn to cook.

Social: Home cooked meals are an awesome offer that people are very likely to take you up on and really appreciate. Cooking well is sexy and makes for an awesome date night. Dinner parties are fantastic well to meet new people and create a vibrant personal and professional network. Taking charge of a meal is a great way to bring your family together or impress your in-laws.

Physical Health: Even if you aren’t bothering with any particular diet (low carb, paleo, etc), cooking at home is almost always going to be more nutritious than food from restaurants. Getting actually healthy food from restaurants/delivery is almost always expensive. Cooking at home is an affordable way to get great nutrition.

Mental Health: This may be more specific to me, but I find cooking to be fantastic for my mental health. In my house I’m the one cooking about 90% of the time and I’m not into the mega meal prep strategies where you cook food for the whole week. So, most days, I’m cooking something fresh for dinner. The need to start cooking prep in time for a reasonable dinner puts a natural stopping point in my work day and then I get to switch to a very focused mono-tasking activity. This routine is, for me, a kind of meditation that separates the work day and let’s my brain process the events of the day.

Meta-learning Tips for Learning to Cook

Learning to cook is not exactly easy. There is an infinite amount of recipes, techniques, resources, diets, and on and on to consume. It can be overwhelming. Learning to cook is almost always laden with failures along the way. You’ll screw up some recipes, ruin some dishes, and get halfway through a complex recipe before realizing you’re missing some essential ingredient. Here are some lessons I’ve learned on how to learn.

Find your YouTube & TikTok muses

There is an infinite amount of cooking content on the internet, but when you find a particular chef or channel that really speaks your language, subscribe and binge their entire backlog. Lots of channels out there will skip essential explanations, use overly exotic ingredients, or complex unnecessary techniques so when you find one that consistently speaks to you, lock it in. Some ones I like:

Have a backup plan

Learning to cook and feeding yourself can be two different things, especially when you are first starting out and failure rates are high. If you are going to try a new recipe for the first time on a busy week night that’s supposed to be your dinner that night (1) go for it! (2) have a frozen pizza or some other quick and easy back up plan ready in case you end up ruining the dish. It’s a really negative feedback loop to mess up a recipe and having to end up eating cereal for dinner, so have a backup plan.

Read/watch the recipe several times well before cooking

Read or watch your recipes carefully, several times, in preparation for trying a new recipe. It’s easy to miss, especially at first, that the recipe actually requires marinating over night, or needs buttermilk or some other ingredient you don’t typically have on hand. Don’t just plop open the recipe book at 7p and start with Step #1.

Stick to a few core cookbooks

Again, it’s easy to get overwhelmed by the millions of cookbooks out there. Like YouTube channels, I recommend finding a few comprehensive cookbooks that work for you and sticking to them for years until you get very confident with a wide variety of techniques. With cookbooks, Kindle will work but having the physical copy can also be really helpful (or honestly I usually get both). Here are some that I recommend:

Essential Concepts

The books and channels above all have great introductions to all of these concepts so I’m not going to try to actually cover them here, but I think it’s useful have a few simple concepts to check off as you read/watch through the first few.

What heat does (chemistry)

Make sure you pay attention to the sections on the basic chemistry of heat. The vast majority of cooking is just different ways applying heat to food and it’s critical to understand what heat is doing to different kinds of foods. For the most part heat is either (1) denaturing proteins or (2) producing a Maillard Reaction. Denaturing proteins is the slow gradual cooking process that turns eggs from runny to scrambled or steak from rare to well done. Different foods have different kinds of proteins which denature at different temperatures and in different ways. The Maillard Reaction is browning (mostly on on meats and vegetables) and happens at very high heat and low moisture environments. Read up on these carefully. Cooking for Geeks covers these the best in my opinion.

Different kinds of heat transfer (physics)

Similarly to understanding what heat does, it’s really important to have a basic grasp of the various methods of applying heat to food. Baking, broiling, roasting, sautéing, braising, searing, sous vide, boiling, and so on, are all just different methods for applying heat. Some, like baking, use convection where the air is heated up around the food, and others, like searing in a pan, use conduction where the heat is transferred directly surface to surface. A cast iron pan takes a very long time to heat up and stays hot for a long time, whereas the air in your oven can dissipate its heat quickly. Understanding these basic concepts will give you the architecture for understanding for why you should keep the oven door closed as much as possible, dry your meat before searing, and pre-heat your heavy pans for longer than your light ones.

Keep it simple

When you are first learning to cook I recommend avoiding complex recipes in favor of simple two or three-part meals where each component is cooked individually. The vast majority of our home-cooked meals involve cooking (a) a protein like fish or meat (b) a vegetable cooked simply, like roasted in olive oil and (c) a starch like rice, potatoes, simple pasta. This let’s you build a healthy meal with simple individual components, master the same techniques with repeat practice, and minimize the risk of blowing up the whole dish.

Make it taste good

This may seem obvious, but it’s important that the food you cook actually taste good. Home-cooked food is almost always healthier than restaurant food, so don’t try to learn to cook and cook the healthiest possible version of each dish. Most veggies taste better roasted in a generous amount of olive oil than they do steamed, so roast them! Baste your chicken in butter. Salt your food generously. Learning to cook by producing dishes that just aren’t that tasty is a very bad feedback loop, so do what you need to to make it taste good.

Don’t cook everything evenly

This is a little more specific but I feel like it needs to be specifically counter-programmed. For some dumb reason a lot people (including myself 10 years ago) got the notion that food needs to be cooked evenly. That it’s really important to constantly turn and shake and rotate your food so that it’s cooked the same all the around and through. This is a great way to make gross food. Stop touching and turning your food. Most dishes are better with a substantial amount of difference in how cooked different sides of the food are: steak with a crunchy sear and medium rare inside, roasted potatoes with a waxy crust and fluffy inside, carrots or asparagus charred on side are all much tastier and mostly produced by having uneven cooking.

Baking is really hard

Really. Baking is much harder and less forgiving than any other kind of cooking. If you’re just starting to get into cooking, don’t start with baking.

Essential Gear

Okay, obviously you can spend and absolute fortune and fill a kitchen with mountains of cooking gear. That’s part of the fun of getting into cooking, let’s be honest. But if all you’ve got is a crappy 10-piece Wal-mart cooking set you got as a wedding gift or a hodge podge you inherited from your roommates, and you need to build your kitchen from scratch, this is the minimum kit I think you need. (Disclosure: most of these are Amazon affiliates links. Don’t click them if that’s a thing that will make you mad).

Pots and Pans

The essential workhorses of cooking. Different kinds of pots and pans provide really different value for money, so I’ll specifically recommend below which ones I think it makes sense to invest in something great that will last versus just get something cheap and replace it every few years. I’ve got a bunch of Amazon links below but I also highly recommend looking up a local restaurant supply store, where you can find high quality equivalents, often for a lot cheaper.

  • A large heavy saute pan. I love this 5.5-quart Cuisinart saute pan. I own two of them and use them in probably 75% of meals. Anything with high straight sides, a heavy base and a lid will do. You’ll use this for searing so it makes sense to get a high quality heavy one here, don’t skimp.
  • A 12″ non-stick skillet (optional an 8″ one too). Non-stick skillets will not last you for decades so I recommend getting a decent quality cheap one. I like these ones from Tramontina. If you only get one, go for 12″ (you can always cook less food in a larger pan but not the reverse) but an 8″ can be useful especially for egg dishes and if cooking for one person.
  • A 12″ stainless steel skillet. If you’re really going for minimalism you can use the heavy saute pan above for everything and skip this. But I find it’s frequent enough that you need to use more than one steel pan simultaneously so I recommend a good one of these. I have two of these from Tramontina.
  • An 8-quart stock pot and 2-quart sauce pan. You need at least one big pot for boiling pasta and potatoes and making stews. Again go for 8-quart or more (if you’re cooking for family) since you can always use less of a larger pot. The sauce pan is slightly less critical but will be used often enough that it makes the cut for essential. This stock pot and this sauce pan, both from Tramontina, are probably a bit nicer and pricier than absolutely necessary but will last. You definitely don’t want tinfoil thin pots here but also there’s not much benefit to getting really nice brands for this.
  • 2-3 baking sheets with wire racks. I use these constantly for roasting veggies, doing messy food prep (prepping a whole chicken is a lot easier in one of these) or for letting meat dry brine in the fridge. You don’t want to get super cheap ones here since they tend to warp which will make all your olive run to one corner when roasting veggies. I like these Nordic Ware ones which come with their own racks. I currently have 4 of these pans and 2 racks which is more than plenty. FYI, the “half sheet” size is actually the typical size that fits most ovens.
  • Optional but cool: a cast iron pan. I think you can honestly skip cast iron when first learning. Cast iron is hard to take care of and can really hold its high heat too long for many beginner cooks. You can use the heavy saucepan above as a substitute for any recipe calling for cast iron. But if you want one, go for it. I have this 12″ Lodge which is cheap enough to just grab it even if it’s not strictly necessary.

Cooking Tools

This is the minimum viable set. No need to get anything fancy.

  • 2-3 sets of stainless steel tongs. This is the essential tool most likely to be missing from basic kitchen setups. I use tongs for every meal and it’s infinitely easier to move food around with tongs versus pushing food around a pan with a spatula. Get at least two in case you touch raw meat with one you don’t have to stop and wash them mid-cook. These ones are fine but honestly anything will do that has this basic shape. I don’t bother with the square wire-shaped tongs which are useless. I also have a set with non-stick tips but there are tons of situations where only the stainless steel will be able to easily grab the food so prioritize those.
  • Fish turner spatula. Not just for fish! Similar to tongs this is the most likely to be missing from basic kitchens and I use it all the time. Get stainless steel for scraping nicely browned food off stainless steal pans or baking sheets. I have this one.
  • Basic set of wooden spoons and spatulas. Literally any of these sets will do fine but make sure there is a flat-tipped spatula in there. Mine is a hodge podge a hodge podge but here’s a decent set (I would add a soup ladle to this too).
  • Micro-plane zester. Yes, you will use this all the time and it’s cheap so it’s in the essential list.
  • Instant read digital cooking thermometer. You need at least one when learning to cook meats. I have this hand-held one and this “probe” style one that can be left in during long slow cooks.

Prep

Almost everything on this list, just get the cheapest version you can find.

  • Stainless Steel Mixing bowls. Just get the most basic set possible. Here’s a ridiculous good deal that includes a bunch of the other items on this list.
  • 4-6 “mis en place” prep bowls. Pre-chopping your ingredients is really helpful when you’re starting. I have eight of these but again the cheapest things you can find will be great.
  • Measuring cup set and large heat-safe glass measuring cup. You need a full set of measuring cups and one of these glass pitcher measuring things (I have a set of 3 but if you only get one go for the 2-cup one).
  • Strainer. You need at least one (I also have a few smaller ones). Get at least one that is large enough that you can lay it across your sink, giving you two hands to pour into it. This is a great one.
  • A dozen or so bar towels. Having these on hand for clean up, drying, and a quick alternative to hot pads is indispensable and will really cut down on your paper towel use. I have, a lot, of these.

Knives

You need just a few knives but you should get decent ones.

  • Chef’s knife. 90% of all knife work happens with this so get a good one. I have this 8″ from Global which is great and I also have the one from Misen, which is considerably cheaper and still pretty great.
  • Pairing knife. Nice and small and useful when the Chef’s knife is too big and unwieldy. Again I have the one from Global but the Misen one is probably great (I don’t have that one).
  • Serrated knife. You need at least one of these. Most folks recommend a bread knife but I don’t find myself cutting huge loaves of bread that often, so I have a serrated utility knife like this one. In general I think you can get by with a cheaper knife when it’s serrated vs a straight edge so feel free to substitute this for something cheaper and prioritize a nice chef’s knife.
  • Honing rod. Get one of these. Learn how to use it. Straighten your knife’s edge before every time you use it. Ceramic ones like this are best.
  • Large cutting board. Get the biggest one that you can reasonably use in your kitchen. There’s nothing more annoying than running out of cutting board space when prepping. I have a comically large one I got at IKEA that barely fits in our sink and it’s a game-changer. This one looks good to me.
  • Smaller plastic cutting boards. Especially if you’re cutting and prepping meat, it can be nice to not have to wash your cutting board mid-prep. I have 3-4 of these.

Storage

Cooking means leftovers so get a good set of storage containers.

  • I have a bunch of these Cambro containers because that’s what chef’s use and I’m a geek. But get any good set of 8-12 containers that nests well.
  • Gallon ziploc bags. I try to avoid disposable things in my cooking but this is the one unavoidable tool for freezing and marinated.

Optional but great

Everything here is not strictly essential but if I had any room left in the budget this is what I would prioritize.

  • Instant Pot. We use this at least once a week to make stews, chili, beans, or rice.
  • Blender or food processor. We have this Vitamix which is about the most lux thing in our kitchen but it’s still going strong five years later and it absolutely handles anything we throw at it.
  • Salt pig and pepper mill. Get yourself some Diamond Crystal Kosher salt and fill up this salt pig. I have no idea why it’s called a salt pig. Fresh peppercorns ground in your own pepper mill (I use this one) is a serious upgrade.
  • Box grater. Handy but very single use so it doesn’t make the essentials list.

And that’s it. It can definitely be a daunting shopping list if starting more or less from scratch but that’s why I started this post with all of the life-long benefits of learning to cook. It’s worth it!

Some Essential Skills & Techniques

Once you have your essential gear, you will need to start practicing some essential skills that are the building blocks of most recipes. All of these are explained in the books I suggested but I wanted to quickly flag the best approach to the most important ones.

Chop & Prep

Don’t re-invent the wheel here. Basically every food item has a well-known best practice for how to chop or otherwise prep it. Just search them on YouTube and learn them one by one as they come up in recipes. Here’s a mega video on how to prep every vegetable.

Searing

Searing requires a Maillard Reaction which means very high heat plus low moisture. Learn how to properly dry your meat and veggies, how to pre-heat appropriately, and how salt interacts with moisture (it pulls it to the surface of meat which can prevent browning). Use high smoke point oils like grapeseed or avocado for searing, not olive oil. Pay special attention this as a good sear versus a mediocre one can make all the difference in some dishes.

Roasting

I love roasting vegetables. Prep them to create flat surfaces that make direct contact with the pan. Minimize moisture so you get browning. Use enough oil. The outside edges of the pan are hotter than the middle so arrange the thicker pieces on the outside. This is a great video with tons of tips for veggies.

Sautée

Pre-heat. Don’t crowd the pan. Learn to test the heat with your hand. Resist the urge to move or shake stuff once you put it in the pan.

Cleaning

Change your sponges regularly. Get some Bar Keepers Friend to deep clean your stainless steel pans. Get this little bottle brush which is made for baby bottles but comes in handy a lot.

Get Cooking

That’s everything I know about how to get started cooking. Get your gear, buy some books, subscribe to some YouTube and TikTok channels and get cooking.

We need a new default funding model for tech companies

There is definitively a small but growing trend of new forms of financing for early/mid-stage tech companies. As a founder and bootstrapper, I feel like I saw the opportunity before I understood why it was there. I wanted to lay out the simple macro framework for why I believe this is just the beginning of a huge shift in how we fund startups.

Premise 1: Almost all new companies are technology companies now

Anil Dash and many others argue that there is no “technology industry” and that the label is too big to be useful.

Almost all companies use tech in some way, just like almost all companies use electricity.

Premise 2: Most companies (tech or not) are not a fit for VC and don’t have alternative options.

And yet there is this totally out-sized relationship between tech companies, which most new companies are, and venture capital, which is definitionally not a fit for the vast majority of companies. So every founder building in software/web/tech thinks they should raise VC when in reality almost none of them should.

But what should they raise? What about debt.

My father took out a loan in the 70s to start his business. That’s how most of the small business entrepreneurs from that era got started. You took out a loan, bought property and equipment, started your business and if you failed the bank foreclosed on your building and equipment, and depending on the loan, maybe your house and personal assets. Seems pretty risky to me but at least it was a well-known pathway to capital for entrepreneurs starting new ventures.

The problem is most tech companies don’t have collateral and you simply can’t get a loan at the earliest stages.

We’ve seen a precipitous drop in new firm startup rates since the early 2000’s. I don’t think my theory here is fully explanatory, but I think part of the problem is the fact that there is no good default financing option for entrepreneurs.

Why it’s all happening now

How did we end up in this position? Jerry Neumann, argues persuasively in this post that we are now in the Deployment Age of the internet/web/mobile technology cycle. This is an application of Carlota Perez’s theories in Technological Revolutions and Financial Capital. This podcast is excellent and compelling that we are past the age of bubbles, crashes, and winner-take-all opportunities specifically in the internet/web/mobile sector. We now get to deploy all the new productivity gains of the web to a ton of new sectors in a much lower risk way.

 

During this phase, new kinds of capital are needed with a different risk-return profile. The easiest comparison for me to wrap my head around is this quote from the post describing the creation of tons of new forms of consumer credit starting in the 20s.

Venture capital, as we think of it, is primarily a feature of the current cycle. Other cycles had other funding mechanisms. E.g.:
The consumer boom of the 1920s was financed through a vast expansion of credit, with personal debt nearly doubling as a proportion of income. And since banks did not make consumer loans, new lending channels had to be created. These included installment sales finance companies (such as the General Motors Finance Company founded in 1919), retail installment lenders (particularly department stores), licensed consumer finance companies (such as the Beneficial Loan Company) and Morris Plan industrial banks4.

 

This is just the beginning

Thus we find ourselves in a moment when there is vast demand to fundamentally re-define the default form of capital for entrepreneurs. It’s an exciting opportunity and a great time to be both an investor and a founder in this space.

Idea Pad: Guest starring customer templates

I recently tweeted one of the best growth/product strategies I know:

 

It’s basically free and can improve almost every aspect of your business if done well. The first three parts are basically good content marketing: interview your customers and learn, post content that highlights them and makes them feel good, and make it easy/beneficial for them to share it their audience. The last piece is what really closes the loop by pulling the best practices from your star current customers into a reusable template (or at minimum a short how-to guide) that your new customers can use to get started.

In the replies, there were several examples of companies doing this really well like:

Ben Orenstein also pointed out that Case Study Buddy is a productized service that offers something quite similar to what I had in mind.

But there’s another level to take this dynamic: create branded templates and use cases from your star customers.

It’s a bit oblique, but this is inspired by what Calm, the meditation app, does by bringing on guest stars to augment their core product: like having Stephen Fry or Matthew McConaughey read stories to help you drift off to sleep.

Airtable does a great job of saying “hey our users are using our product to make a CRM, let’s make a CRM template they can use” but what if they worked with a well-known VC super-connector to design the Jason Calcanis CRM template based on how he manages inbound contacts. Instead of “Content Calendar” they worked with Recode to produce a “how Recode does content scheduling template.” Email marketing software could have built-in templates in collaboration with top brands or well-known educators who build courses and systems. If your product can be themed, work with a few top designers to add extra credibility to your base themes (pay the designers or give them affiliate commission). This doesn’t work for every product, but I think it would be a winner for quite a lot of them.

PS – it’s a new year and like everybody, my pseudo-resolution is to write more. So be prepared for more half-baked ideas like this getting out of my head and into your feed.

 

How I email

In 2019 I’m transitioning into the role of an investor at Earnest Capital. Since we soft-launched in October with a call to collaboratively build investment terms for “funding for bootstrappers” I have received 100x the normal volume of emails that I’m used to processing. Looking forward it seems clear that being an investor in early-stage startups means becoming a professional emailer. As I’ll be spending most of my day in email1, I thought it would be a good idea to explicitly state my email preferences somewhere I can link to.

This should simply be viewed as a list of my preferences, not some list of demands that must be complied with in order to email me2.

Things I think about email

  1. Many VCs seem to view responsiveness as a competitive advantage, replying near-instantly at all hours. I’m not sure that’s a factor I want to optimize for but even if it were, I know I would never be an exceptionally fast responder. So I’m not going to compete on responsiveness. If you’re used to dealing with VCs and getting instant responses, emailing Earnest might seem jarringly slow but I’m okay with that.
  2. I optimize for completeness in a response. I prefer not to trade 25 half-baked emails back and forth when I could wait for all the facts I need and write a detailed, clear, complete response.
  3. I am remote-first and I prefer emails as the default mode of communication. Switching to scheduling a call the moment an issue becomes complex is a habit I don’t share. Let’s be thoughtful, clarify our thoughts in writing, and use a call as a last resort (or just something that’s fun but not necessary).
  4. I don’t do Inbox Zero. I used to, but feel that I frequently need more time for responses to marinate than an instant ‘respond, delay, delegate’ protocol allows.
  5. I do view my inbox as “other peoples’ todo list” and try to allocate my day first toward larger projects that will improve Earnest for everybody, then dive into my inbox.

My email preferences

  • I like long emails. I’m not one of those people who needs to get all the information in the first 3 sentences or I stop reading.
  • Follow-up as much as necessary. If I haven’t responded to your email, it doesn’t mean I won’t. I am most likely working on something else integral to a reply. Feel free to send additional follow-ups if there is new information. I prefer not to get a daily stream of “just bumping this to the top of your inbox”—though one or two is fine.
  • Please let me know explicitly if my default mode is not going to be appropriate. “I really need an answer on this by {datetime} because {reason}” is really helpful for me.
  • Don’t apologize. If we agree that sending me an email does not obligate me to send back an immediate response, there’s no need to apologize ✌️

Myers Briggs for Email?

We all spend so much of our lives writing and reading emails. Many people have radically different styles and preferences. I wish more people would explicitly write out their email preferences. Eventually, we’ll categorize and group them into themes like a Myers Briggs for email. So just as you can short-hand with “I’m an INTJ” and confer a lot of information on how you prefer to interact, you can say “I prefer my email as Correspondence” or “I’m an aggressive Inbox Zero-er” and confer a lot of the preferences above. I view my email preferences as Correspondence in reference to how people used to communicate when hand-delivered letters might take months to be delivered by ship. You had to be thoughtful and clear and close as many open loops as possible.


  1. I’m using Superhuman these days as I write this.

  2.  hat tip to @devonzuegel for the inspiration for this