Prediction #12: The Rise Of The Bootstrap Entrepreneur

We are in the early stages of a new era and type of entrepreneurship.

The Covid situation has opened up a whole new set of needs in terms of managing remote workforces, sanitation, telehealth, and other areas many of which will not fully go away.

In addition to these new needs, there is now going to be a large supply of entrepreneurial tinkerers. As a large portion of startup employees are now working from home (or are laid off) and as a large number of recent graduates find they cannot get new jobs, we now have a large population with the opportunity and time to start new ventures.

Pre-covid, employees working in an office would find it hard to run a side business as it would have been frowned upon by peers who saw you doing it, and there are legal ramifications such as who owns the idea if you started it at your employer’s site? Now that those people are working from home with an additional 90 minutes from no commutes, expect more people to start and manage side hustles – some of which will turn to big businesses.    

Meanwhile, recent graduates – and current students- who struggle with getting employment are now going to find themselves tinkering with new ideas to generate cash on the side.

Some of these new businesses will be VC backable, but due to barriers to discovering this new talent, the fact that everyone is remote (so it is hard to build a typical “startup office”) and entrepreneur’s need to immediately pay the bills, a lot more are going to be smaller bootstrapped ventures.

The pre-covid model was 1) leave your job, 2) work full time on a new billion-dollar idea, 3) get angel/seed funding, 4) find some expensive cool office space.  

Today’s model may be to 1) Start working on a side project on the “commute” hours from your new work-from-home environment, 2) Focus on smaller but profitable ventures that can bring in cash now, 3) build it out remotely.

This means building smaller, much faster companies. Many will be started with small amounts of cash using tools like no-code to get prototypes going. It will also mean more remote-first companies with remote support staff (remote lawyers, accountants, design contractors).

The old Angel->VC->Huge exit pathway is not going to go away. And obviously, some spaces (like remote work, biopharma) are going to be hot. But overall, I think we will see a plethora of smaller, cash-flow style businesses with a few that later become huge – similar to say 1996 or 2004.


  • Finance for smaller, bootstrappable cash-flow businesses (I believe is doing this).
  • Development tools or companies that can convert no-code to full-code. At some point, people will exhaust their no-code tools
  • Support teams for new startup ventures
  • SaaS service tools for managing smaller businesses (look at for accounting, but there will be others for outsourcing small business support, marketing,etc…).

If you currently are working on one of these opportunities or want to work on them, please contact me at charlie at iamcharliegraham dot com

Prediction 8: Dine-in “Experiences” will be significantly curtailed as 30% of restaurants go out of business.

NOTE: this was written in May but I got around to posting it now. Still, much of it is relevant.

Currently, approximately 3% of restaurants have closed down due to the pandemic. Expect that to grow to 20-30% by the time we are done. As restrictions open up, restaurants are going to have to comply with new sanitation/disinfection measures as well as physical isolation including having chairs not facing each other, shorter dining durations, preferences towards outdoor dining, and physical separation. Given a likelihood to wear masks, the once casual, enjoyable experience will become much more stressful with constant reminders of the hidden virus. Due to these factors, I expect in-person restaurant traffic will remain at 30-50% lower levels for the next 12-18 months. Fast-food, takeout, outdoor and short stay restaurants will handle this better as people will be more likely to do shorter trips. Restaurants that are well suited to takeout/delivery will shift almost exclusively to that model as they will not be able to financially support keeping a restaurant open at max 50% capacity.

Many restaurants that are suitable for pickup/delivery will survive based on that model. Think Thai, Burmese, Chinese – where the cuisine is the main driver to the restaurant (vs the indoor experience) and the cuisine can hold up to a 15-minute wait in a box.  

Luxury/fancy/experiential restaurants catering to long meals and business meals will suffer the most either shutting down or doubling down on exclusivity and price. Restaurants with the capability will expand their outdoor seating, including -with a city’s help – expanding into sidewalks and streets. Food trucks -which cater to to-go and outdoor eating – should also thrive.


  • Expect a huge increase in the convenience of curbside pickup. Rather than paying the price (and suffering the wait) for delivery, restaurants will allow you to schedule a time to pick up, text when you have arrived, and then drop the item in your car while you double-park. Popularity for curbside pickup will grow as people realize it is faster and more pleasurable than going into a store for a pickup. 
  • A new “contactless pickup-only” style restaurant will emerge that only provides contactless pickup. Think of it as the next generation of drive-through. Starbucks and Sonic have shown this model to work and it will continue with others.
  • Expect luxury restaurants to pivot to completely “private dining” with pods of isolated private, highly ventilated rooms – perhaps each with a virus destroying ventilation device like a Molekule Air Pro RX.
  • Expansion of food trucks and extensions of “Off The Grid” type programs where groups of food trucks will support a park or open area with chairs and outdoor seating.
  • “Ghost Kitchens” – Kitchens and restaurants made entirely for delivery services like UberEats.
  • Tools to enable online ordering for food trucks.
  • Companies offering disposable dining ware should see a long-term explosion in growth.

If you currently are working on one of these opportunities or want to work on them, please contact me at charlie at iamcharliegraham dot com

Observations and 5 Predictions for the Apple Watch


I’ve now owned an Apple Watch for around 4 months. I bought it because a) I wanted to live in the future (and I think we will all be wearing some type of wearable in the future) and b) because I am testing out a few new ideas on it. I read many articles, talked to about a dozen people who own one and heard the full spectrum of opinions.

When asked what I think about the watch, I describe it with one word: potential.  Today’s version 1 of the watch (or v1.5 now that OS2 is out)  is not yet a must-have product:  it can be horribly slow, the battery dies quickly and there is no real killer app, but I get enough small “wow” moments that I think a future version will be amazing.

Here are 5 predictions for how future versions of the watch will realize its potential.

  • The Watch (and smart wearables) will eventually transform payments. I have had Apple Pay on my iPhone for at least a year and never was impressed with it.  Apple Pay on the watch, on the other hand, is a wow experience.  I push a button on my watch and my payment in the store is complete. For the first time we have an experience that is faster and easier than pulling a credit card out of your wallet.  It will take time to build out the network effects but my guess is that using smart wearables like the Watch to pay will start taking off now that credit card payment systems are switching to chip readers which feel even slower than swiping.
  • The watch will be appreciated more by women.  One great feature of the watch is that it stops you from taking out your phone all the time.  If you get a call or text, instead of fumbling for your phone, you can just quickly peek at your watch.  This is a nice to have for men since their phone is in their pocket but is much more useful for women who usually keep their phone tucked away in a purse where the message gets lost.  I expect women will continue to be more excited about the watch as less bulky, more fashionable and smaller versions of it come to market. (You can see this starting to emerge with yesterday’s launch of the Hermes Apple Watch)
  • The watch (and its descendants) will eventually end the popularity of Fitbit and activity tracking devices.  The first version of the Apple Watch already has an activity monitor on par with Fitbit.  But on top of that it also comes with a lot more functionality (you can use it as a phone, send/receive text messages etc…).  Given that people will only want one (if any) device on their wrist, they’ll end up going for the one with the most functionality.  iPod/music device sales plummeted once the iphone came out and without a drastic change the same thing will happen to the activity monitors as smartwatches gain popularity.
  • The Watch (and its descendants) will usher in a number of new and useful apps that were previously not possible.  I have not yet seen a must-have 3rd party app on the watch but that might change now that WatchOS2 allows much more functionality.  Apps I could imagine would include:
    • Haptic feedback apps (or apps based on vibrations ) as their main feature. For example, musicians will soon have a vibrating metronome on their wrist taping them at a regular interval so that they can keep a consistent rhythm.  You could also imagine a “SpeakerTap” watch app where a public speaker (like a Presidential candidate during a debate or a salesperson during a big presentation)  could be discreetly notified if they are going off message.  
    • Gesture-based apps:  You could imagine a minority-report type app where waving your hand will cause changes on your screen or an app that turns a chopstick into a Harry Potter wand if you hold it in your watch hand.  Nintendo Wii and a bunch of other controllers already support this type of functionality but you still have to find and hold a controller. Anyone with a smartwatch now has an accelerometer, computer and gyroscope always on their wrist which makes the functionality much more convenient. 
  • Future versions of the watch will turn into 24/7 health-tracking devices.  Rumor has it that Apple really had to tone down what they put into the first watch to have it launch early 2015.  The next version of the watch will likely have GPS (which is already in other watches), and many more health sensors such as oxygen-reading and blood pressure sensors.  Given Apple’s recent forays into health, my guess is that they want to eventually become a complete 24/7 health-tracking device that will monitor your health (and the health of your loved ones) 24/7 and notify you of any changes before things become critical.

In short, I still think V1 of the Apple Watch is a niche novelty, but from what I have seen and experienced I am bullish on its future potential.

Shop It To Me In Forbes and Hacker News

Two fun news pieces for Shop It To Me today!

1) Forbes just posted a great Q&A about myself and Shop It To Me as part of their designer spotlight series.  Check it out!

2) We just announced in our blog that we recently removed passwords completely from our Shop It To Me iOS app .   We’re really proud of this accomplishment as our app members no longer need to create and remember a unique password when they sign up or log in and we hope other app developers will follow suit.    Currently it’s gaining attention as the post is a top-10 listing on Hacker News.

Let us know what you think and Happy Thursday!



It’s Time To Get Emotional

At Shop It To Me we are customer-driven so we think about product a lot. We’ve noticed that too many Internet companies today think about their product almost exclusively in terms of a functional experience. What need are we serving? What solution do we provide?  What features should we add?  Recent books and blogs encourage that by having you ask questions like “what problem are you trying to solve?”, “what is the pain point you are addressing”?

Those questions are certainly important to answer, but if you want to build a deep connection with your users or customers, you will also need to answer a much more important question: What emotion should customers be feeling when using your service?

Successful consumer products are often valued more for the emotion they generate than the tangible value they provide.  If you look at almost all successful marketing campaigns, you’ll see the deep emotion behind it.  CPG companies are particularly amazing at figuring this out.

Some examples:

  • Michelin Tires are not just tires to help your car move.  They embody safety, security, protection. Michelin ads are all about safety — they have either a huge puffy mascot (who looks like an airbag), or a baby riding inside the tires.  With these tires, you not only have wheels to move your car, you can feel rest-assured your kids and the things you care deeply about will be safe.
  • CocaCola is not just carbonated sugar. It’s bottled up happiness.  Their ads (Happiness Machine, Sleepwaking) all show happiness in unlikely circumstances, and their tagline “Open Happiness” is a pretty obvious connection on how they want you to feel when you open a bottle. .

Having a strong emotional connection is not just for physical consumer products.  It is important for any online service or product as it can have a major impact on who uses the product, when they use it, what you can charge and your overall product’s success.

Take two recent mobile-based taxi-alternatives:  Lyft & Uber.  Both are trying to solve the same problem:  I need to get somewhere now and there is no taxi available.  But both are building different relationships with their users by touching upon very different emotions.

Uber’s messaging and service is built to make you feel pampered, like a high-powered executive.  They primarily use black cars or nice hybrid SUVs to pick you up.  Their site is in classic silver and black with a luxury car featured.  Their tagline “everyone’s private driver” —  reinforces the emotion.   With Uber, you are like the guy in the back of the limo passing the bottle of Grey Poupon.


Lyft is taking almost the opposite end of the spectrum.  They are focusing on being your pal.  Instead of black cars, they solicit regular people to be their drivers.   All of their cars identify themselves with quirky pink mustaches.   Their domain name is a quirky as opposed to a more standard   They encourage you to sit in the front seat and fist-pump the driver when you enter and exit.   Lyft is less like having a private driver, and more like having a friend who today is your designated driver.

 Screen Shot 2013-06-25 at 9.03.53 AM

Based on the marketing alone, one would expect very different experiences with the two services. Want a professional, polite, quiet driver?  Use Uber.  Want a friendly conversation and a quirky fun, low-key experience?  Choose Lyft.

If your business is in a crowded marketplace, creating a strong emotion can be a huge differentiator.    Bottled water is pretty commoditized, and yet companies like VOSS can thrive by creating a product more than 2x the price of the rest of the market (and therefore generate many more profits) because they aren’t just delivering water, they are delivering on the feelings of luxury, stylishness and exclusivity.

At Shop It To Me, we are constantly looking at not just what we do (giving you updates on what you want) but what emotions we want you to feel (smart, in-the-know, excited, accomplished).  Because while the service may help fill a need, it is the emotions that users will remember.

So next time you are thinking about your value proposition or what need you are serving, don’t just stop at the services and features.  Take the time and think about the key emotions you want your users to feel when you successfully fulfill their needs and you’ll end up building a much longer-lasting relationship.


Building An Indispensable Product

At Shop It To Me, we believe a key way companies disrupt a market and have long term loyalty is by building not just a great product or a insanely fun product, but an indispensable product.

Look at some of the services today with the most avid users — Google Search,  Apple’s iPhone (when it first came out), Twitter, Etsy, eBay, Pinterest — all have one thing in common:  They all have built a product that for some audience is indispensable.

What is indispensable?

So, what exactly is an indispensable product?  I believe you can divide it into three different components:

1) An indispensable product solves an important or meaningful problem.  

Every indispensable product out there solves important problems for its users. VCs often refer to this as as the “aspirin” vs “vitamin” scenario (whenever you have a headache or pain, aspirin is a must-have;  vitamins are a nice-to-have).

There’s a reason Google Search is so popular —   It is indispensable in two ways.  Users of Google search trust it to give them answers to the most important questions.  For advertisers, Google SEM and SEO has traditionally been the best place to find customers with active intent to buy their service.    Selling your amazing new tax software for businesses? Get to be at the top of the search results for “business tax software” and you’ll have the huge number of highly targeted leads you need to crush your quarterly goals.

2) An indispensable product has no good substitutes.

To gain real traction, an indispensable product not only needs to solve an important need; it must lack good substitutes when it first comes out.  You can’t have your product be indispensable if users can easily find an alternative.

When the Apple iPhone first came out, there were no other products remotely like it.  It was terrible as an actual phone, but it was the only phone out there for consumers that would let you actually search and view real web pages (as opposed to just mobile versions), or see your emails in a visually appealing and simple way.

If you want to build an indispensable product, you need to make your product unique for the customers you are going after — you can’t just be a slightly better version of a popular product and expect people to switch.

3) An indispensable product is ideally something you need on a frequent basis.

The third point is not a true requirement of indispensability, but an important attribute if you want to build a habit and get frequent usage.   If people find your product indispensable but only need it once every 5 years (or once at all), you may have a great product, but you won’t be building a habit for when competitors enter the space.   On the other hand, if people need your product frequently, you’ve got the ability to train them to be accustomed to your service which will keep users coming back long after other competitors make similar products.  (Think of the millions of people still using MyYahoo! 10 years later)

A quick test for indispensability

So you think your product has all three of the criteria for an indispensable product; how do you know for sure it’s indispensable?  Here’s one easy test: take it away from your users and see how they react. If people start screaming that the service you provide is gone, there’s a pretty decent chance you have an indispensable product.

Think about the products that are indispensable to you.   Smartphones, webmail, Twitter  are all indispensable to certain people.  (Think of how people tense up when their phone goes missing for 15 minutes, or how a reporter would feel if they could not access the Twitter feed and had to wait until news appeared on a website).

We know our Shop It To Me emails can be indispensable from inadvertent tests.  Every once in a while our emails get delayed and when that happens, we often know about it not only from our data but from our support box —  users email us demanding (occasionally with profanity) why their salemail had not yet arrived .   And with our new product,  Shop It To Me Threads, we occasionally test the waters of indispensability by asking user-testers how they would feel if we removed certain features.    We’ve had a number of features that users say are “really great” that we removed from our system because they didn’t notice when it was gone.

So for all of you working on the next big thing:  As you build out your product, and start prioritizing features — figure out what parts are need to make your product more indispensable and focus your energies on that.  You’ll build a stronger product and have a much larger chance of turning your idea into a wild success.


What our customers say vs what they mean

My latest article on what customers say vs what they mean  and what you should do about itwas just posted at!

Here’s a snippet…

You know this meme: You hear one thing, but it probably means something else entirely. (Like when my wife says “Don’t worry about it,” it usually means, “It’s important. Worry.”) You’ve probably seen these sorts of lists for relationships,Americans, or maybe venture capitalists.

But funny as the jokes can be, the kidding stops when it comes to your customers–because knowing what they really want is critical to your business.

We’ve interviewed hundreds of users of our service and we found some common discrepancies between what they say and what they actually mean. Here are eight common comments, translated for you–plus some advice on what you should and shouldn’t do about it.

‘Your website should be more like [your competitor’s].’

  • What they mean: “I really like [your competitor] and think your site is pretty close to theirs, but I really prefer Site X.”
  • Don’t: Just make your site more like Site X.
  • Do: Figure out what makes you different, and change your site to reflect that. You want your site to be so different from your competitor’s that there really is no comparison.

To see the whole list, go to the article at

How to build a culture of experimentation

As you have probably noticed from my blog — at Shop It To Me, we are big fans of experimentation.   I believe to succeed you can’t just treat experimentation with lip-service.  It needs to be ingrained in your culture.

For those of you who want to start experimenting in your company, I just posted an article on  How To Build a Company Culture of Experimentation at Mashable.  Take a look!


Why you should be user-testing…now.

If you are developing a new product, chances are you want to wait to show it to anyone to critique until you have it mostly in place.

Why? You have a great vision as to where the product is going and you want them to see the final realized product before making any judgments.  Cooks don’t pass along half-cooked meals to try…why should you with your creation?

Well actually, cooks do put menu items they are working on in front of real people all the time:  they become “daily” or “seasonal specials”.  If the special does poorly, it’s back to the drawing board; if the special does great — it finds its way onto the permanent menu.

The reality is, you as an expert in your field suffer from what the Heath brothers call the Curse of Knowledge.  When you are building out a product, you spend almost every waking hour thinking about the nuances of how it will work.  You live it, dream it, breathe it.  That’s awesome and super-important.  BUT… you have now spent so much time thinking about a product that it is impossible for you to see it through the eyes of someone who has never experienced it.

When a user tries your service for the first time, they won’t know all of the things that seem completely obvious in your head.   They are just trying to understand your great idea for the first time.

Enter user-testing.   Every time you are releasing a new feature, put it in front of users in your target audience who you have never asked…. Constant user-testing will allow you to find problems earlier than expected and figure out solutions to those problems that you might not have come up with on your own.

Do a few user tests and you’ll be surprised.  Sometimes very surprised.  You’ll end up building a much better product for it.  But to really succeed, you should be doing that (and AB testing) all the time.

So, how do you get started?

You don’t need a big firm to get results.  Basic or what I call “scrappy” user testing will get you pretty far and is pretty inexpensive and easy to do.

1) If you don’t own it already, buy Rocket Surgery Made Easy.  It’s a great overview of user-testing with great instructions and many more reasons why you should do it.  It’s a super quick read and provides a great guideline/framework.

2) Then get a pipeline of users in place.  So how will you get people?  Just ask.   Email a variety of current / prospective users.  If you are just getting off the ground, use your networks.  Ask your friends for their friends.  Post on Facebook and LinkedIn.  Ask people in your building.   You’ll be surprised.   Most people who would be your customers would get excited about being able to test things before anyone else and to have their feedback matter.  It’s worth much more to them than any other compensation.

3) Figure out things you can test now.  If you just have a mockup, you can test it by showing it to people and asking what stands out, what they think different sections would do and how they would perform a task.   If you have a half-working product –that’s ok too.  Just to set expectations appropriately:  You are not trying to figure out if they will love or even use your product  (it’s really hard to get accurate answers to this user-testing).  Instead, you want to know — where are they confused?  What makes sense and what doesn’t?     What do they see and what do they completely ignore?

4) Schedule all of your user testers to start on the same day. It will allow you to get all of your materials together and you won’t put too much emphasis on one person’s opinion. Later,  you can start setting a weekly schedule or bi-weekly user-testing day so you can build it into a habit (At Shop It To Me, we do ours on Wednesdays).

5) Make it accessible to everyone on your team and encourage them to watch it.  We use skype screen sharing as well as Silverback for recording.  We also transcribe the session into Google Docs for people who want a quick read (this does introduce some author/transcriber biases, but in the end we feel it is better than not having it).

6) Then just do it.  It will be eye opening.   Trust me.

Even if you aren’t building out a product, get a feel of what it is like by participating in a user-testing session.  As I said above, we generally user-test at Shop It To Me on Wednesdays.  So if you ever want to user-test our new products and see what it’s all about, just send me a line!  We’d love to have you!


Business Lessons from my 10-month Old

Just in time for Father’s day, I wrote a new article for called “Business Lessons from my 10-month old”.  Enjoy!