I was having a conversation with a founder last week about *boring companies.* (No, not *that* [Boring Company](https://www.boringcompany.com/)). Specifically, how important it is for today’s entrepreneur to not overlook opportunities in the mundane aspects of daily life.

There will always be something new and shiny to chase. Web3 is still hot, and industries that were cool a decade ago are making a roaring comeback (looking at you, startups in fintech).

It’s never been easier to get caught in FOMO. For every startup idea that’s boring, a hundred others are catching the eye of VC’s and media. No wonder [so many startups pivoted to web3/blockchain technology in 2020 and 2021](https://www.vice.com/en/article/jgmyzk/the-pivot-to-web3-is-going-to-get-people-hurt) (no comment on the amount of startups that *pivoted away from web3 when the markets tanked).*

I get it. It makes sense to be working in an industry everyone is talking about… doesn’t it? But when you zoom out and look at the everyday life of everyday people, a stark reality materializes: **the businesses that help us enjoy daily life are *boring businesses.***

Gas stations so you can commute. Cleaning supplies so you can maintain a happy home. Landscaping and gardening services so you can win “yard of the month.” Fiber and communication lines so you can stream [more than you ever have before](https://www.bloomberg.com/graphics/2021-tv-streaming-deals-best-bundle-options-netflix-hulu-disney). Sanitation services so you won’t live in filth. Storage facilities so you can store those holiday decorations. And on and on.

It’s nearly impossible to live an American life without touching these businesses. They’re incredible opportunities usually with a huge [TAM](https://corporatefinanceinstitute.com/resources/knowledge/strategy/total-addressable-market-tam/), recession-resistant services, and low barriers to entry.

Why then, are so many founders unwilling to enter these markets?

Some of the reason might be FOMO/wanting to be on the cutting edge of technology. (Building “the future of Internet” is *a lot sexier* than streamlining transportation logistics.) Perhaps the fact that boring businesses lack venture scale is another reason. (It’s unlikely your gardening company is going to be the next unicorn.) Or maybe it’s because boring business opportunities are “out of sight, out of mind”? (When was the last time you thought about [soil infiltration testing](https://www.centralgeotech.com/uncategorized/what-is-an-infiltration-test/) when you passed a new housing development?)

I believe there is no better time than right now to build a *boring business,* and solve *boring problems*. Consumer sentiment, market demand, and the emergence of new technology have created a perfect storm for these opportunities: just this week, I spoke to a startup who is working to revolutionize healthcare payments. *Healthcare payments.* It doesn’t get more “boring” than that, yet the opportunity is unlimited.

If you’re a founder looking for something real that has a sustainable, tangible impact, consider starting a *boring business.*

Here’s why.

---

## Boring businesses have a massive TAM.

Huge markets aren’t just in SAAS and aren’t just new opportunities like web3: they’re everywhere. (Many of these opportunities are stuck in markets coined as “already won” by incumbent businesses.)

Surprise, surprise: a market appearing to be “won” doesn’t mean there won’t be room for your venture.

Just take a look at the [Figma acquisition by Adobe](https://www.forbes.com/sites/petercohan/2022/09/16/adobes-20-billion-figma-buy-to-boost-top-line-growth/?sh=6ed604a260bb). Many people said that design tooling was a market *already won* by Adobe. Yet Figma still managed to carve out a massive chunk of that market, craft tools that are used by millions of teams, and get acquired for $20B—one of the largest private acquisitions in history.

So let’s use a common boring business as an example: self-storage. The USA self storage market isn’t one to laugh at: it’s $50B+ with CAGR 5%+ and plenty of room for growth. [According to the US Census Bureau, construction spending on self-storage has increased by 584% from January 2015 to January 2020](https://www.mordorintelligence.com/industry-reports/united-states-self-storage-market), and the industry is seeing a huge boost from COVID as e-commerce brands are opting for inventory storage space, no longer needing brick-and-mortar storefronts.

Self-storage is a perfect boring business because the consumer *already understands* the product, need, and offerings. Antiquated incumbent brands are still running the show (which provides a wedge for a forward-thinking entrepreneur to shake things up), and self-storage is widely used across socioeconomic classes: those with lesser means and those with plentiful means still use various forms of storage services.

Why does this matter? It’s *incredibly difficult* to establish a new market worth billions—often taking decades. Always looking to “define a new market” keeps huge amounts of opportunity off the table.

(And it's not just self-storage. This story plays out again and again in other markets—huge TAM, tons of opportunity to build value in your venture, plenty of room for growth.) ¹

## Boring businesses offer accessible wedges for entry.

Back to our self-storage example. With boring businesses, just doing things *in a more modern way* can create incredible value. [CubeSmart](https://www.cubesmart.com/), for example, became one of the largest players in the self-storage industry ([market cap of $9.73B](https://g.co/kgs/qdnUiq)) by offering a simple value proposition: *they allowed customers to manage their storage unit on an app and through online services.*

That’s right. What you and I have been doing for over a decade—managing things online and through apps—CubeSmart used as a value proposition to build a multi-billion-dollar empire in an industry where meeting in person was the norm.

Of course they’ve done other things correctly as well: [healthy balance sheets and prioritizing high-quality customer experiences, just to name two](https://seekingalpha.com/article/4496722-cubesmart-high-yield-opportunity). But their edge came from their *modern approach:* surrounded by a “this is how things have always been done” mentality, CubeSmart was bold enough to shake things up. Now they’re getting rewarded for it.

How valuable would it be to you as a consumer if you could access your medical records from anywhere in the world and share them confidentially? What about never needing a REALTOR® to buy a house again? (Consumer-friendly app-based transactions are something I’ll talk more about in the future.)

You get my point.

Simple, modern solutions in antiquated industries bring huge returns.

It’s not lost on me that *actually doing these things* isn’t easy—the only “easy” way to make money would be if you’d bought $1M worth of Bitcoin in 2013. But the solutions are often *straightforward:* doing something well, aided with the use of technology, in an industry that’s trailing behind consumer expectations, is the gameplay for winning in your boring business.

## Boring businesses are recession-resistant.

Notice I said “recession-resistant” and not “recession-proof.” If 2020 and 2022 have proved anything, it’s that *no industry is fully recession-proof.* Even still, boring businesses fluctuate less than others.

As an example, many of the exciting web3 startups that were all the rage in 2020 and 2021 have quietly been moving into other domains. [@GergelyOrosz](https://twitter.com/GergelyOrosz) says it well:

```cv
tweet
https://twitter.com/GergelyOrosz/status/1568505516069998593?s=20&t=VmpT5ijN_ASK6cvxaPat1g
```

The issue with businesses that rely on people having free money to spend, is that *they die when consumers run out of extra income.*

By contrast, [there is nearly a $100B market in the USA for waste disposal services](https://www.inc.com/alex-moazed/how-to-claim-a-piece-of-the-100-billion-waste-management-opportunity.html) with [CAGR over 6%](https://www.grandviewresearch.com/industry-analysis/global-waste-management-market). Waste disposal isn’t going anywhere (and people still pay for those services when markets are down).

Again, the labor isn’t sexy—waste disposal jobs [quite literally dominate the list of dirty jobs](https://en.wikipedia.org/wiki/List_of_Dirty_Jobs_episodes) from the TV show, *Dirty Jobs—*but it is profitable (and profitable ventures are sexy by default).

## What does this mean for you?

Am I saying that you need to drop everything and go pick up a garbage can?

No, not at all.

What I *am saying* is not to overlook the opportunity of building a massive business in industries that are considered outdated, unsexy, and *boring.*

Next time you get in your car, notice the trillions of dollars that exist around you in ventures you hadn’t recognized before... perhaps bringing a modern approach to one of these ordinary industries is your next move?

One thing is certain: the opportunity of boring businesses will be “[missed by most people because \[they’re\] dressed in overalls and \[look like\] work](https://www.brainyquote.com/quotes/thomas_a_edison_104931).”

---

¹ See also: [the $43B transportation logistics market](https://www.grandviewresearch.com/industry-analysis/us-retail-logistics-market-report) or the [$105B landscaping services market](https://www.landscapeprofessionals.org/LP/About/Industry-Statistics/LP/Media/landscape-industry-statistics.aspx).

The Case for Boring Companies

Until [Basewell](https://www.basewell.com/), bootstrapping was all I knew.

My real estate venture, for example, was *really* bootstrapped. I’m talking about not being able to afford groceries or gas kind of bootstrapped. I’m talking about not being able to take clients out for drinks because I was under 21 *and* couldn’t afford the tab kind of bootstrapped. I’m talking about breaking down in my car because I didn’t know “how the hell I was going to do this” kind of bootstrapped.

Those years of fighting taught me drive, determination, and developed a sense of grit that’s unshakable. But not all bootstrapping is made equal.

There’s the bootstrapping that’s cute—mainly found on Twitter and TikTok. It’s the “daily hustle” videos of founders vlogging their seemingly perfect bootstrapped life where they rise before the sun, work out, eat perfectly, close a million-dollar deal with a big new client, and save a kitten—all before 7 AM. No investors, no rigorous schedule, no accountability. It’s like a Disney adaptation of what being a founder is like.

In contrast, real bootstrapping stems from *deep desperation,* experienced by founders who are willing to make things work despite their circumstances. Bootstrapping is most often a last resort, not the first option.

Yes, some incredible resources do exist to assist the bootstrapped entrepreneur: [MicroAcquire](https://microacquire.com/), for example, is a marketplace I wish existed years ago, and robust manuals like Seth Godin’s *[The Bootstrapper Bible ](https://seths.blog/wp-content/uploads/2013/09/8.01.bootstrappersbible-1.pdf)*eliminate the noise and help bootstrapped founders build an enduring venture.

Even still, the “build something that works, or die” mentality drives every decision. It’s a pressure that never subsides… and as your success grows, the PTSD from building at day 0 will always live rent-free in your head. It’s the curse of the bootstrapped entrepreneur.

[In a recent member newsletter](https://newsletter.evanstewart.xyz/p/market-killing-your-startup), I wrote how “the market” is *one of many* factors killing startups right now, and I advocated for founders to embrace principled decision-making. Shipping profitable products, embracing customer feedback, learning from mistakes, adapting quickly, and being a good steward of your startup’s finances are all important characteristics that can get lost in a bear market.

Many founders know this, but bootstrapped founders usually *feel* this on a more intimate level—and definitely experience market highs and lows faster than those with venture backing. If the customer doesn’t like your product, venture dollars aren’t coming to save you. “[Default alive](http://www.paulgraham.com/aord.html)” isn’t an option.

Orlando says it well in his recent tweet:

```cv
tweet
https://twitter.com/OrlandoBravoTB/status/1579589790261207042?s=20&t=jiJQfi6rOn7jEzmYQyibqA
```

Markets where capital flows like wine get undisciplined founders drunk.

And that’s where we’ve landed. For many, sobering up has been difficult. Raising is off the table, customers are clenching their pocketbooks, and runways are getting *awfully short.* To the founder with previous bootstrapping experience, not having a golden parachute means the chaos of this year is *just another day.*

*Venture markets are crashing and you can’t raise?* Just another day.

*Customers need to be convinced to buy your product?* Just another day.

*Talent is hard to hire and scared to commit?* Just another day.

*Your access to groups of people, companies, events, or markets has closed?* Just another day.

Starting with nothing demands resourcefulness that’s only taught through *doing* the thing. This market rewards those who have the tenacity to push through, or who know what it’s like to fight back against seemingly insurmountable odds.

That’s why I believe founders who have previously bootstrapped make fantastic stewards of venture backing—especially in crazy markets like this one. Overcoming adversity to their startup is all they’ve known.

“Been here before. Just another day.”

```cv
tweet
https://twitter.com/heyecs/status/1560310588550418432?s=20&t=N87fUHJ0eHfdnHWtLgA6qw
```

Contrary to what TechCrunch articles would lead you to believe, *most businesses* start with a bootstrapped approach—not $5M in pre-seed funding. Those startups might go on to raise venture later, or they might follow in the footsteps of [Profitwell](https://www.profitwell.com/paddle) (bootstrapped, sold to Paddle for $200M+) or Mailchimp (bootstrapped, [sold to Intuit for $12B](https://www.forbes.com/sites/kenrickcai/2021/09/13/mailchimp-intuit-acquisition-billionaires-ben-chestnut-dan-kurzius/?sh=500ed7396093)). Yet the narrative of *options* is not entirely true for all people: some founders never get the choice to raise, regardless of their intentions to do so or the health of their EBITDA.

It can actually be difficult for bootstrapped founders to get their foot in the door with investors. Often bootstrapping is the *only option* for those who lack network connections to VCs, or [fall outside of the typical SF founder mold](https://pitchbook.com/news/articles/female-founders-dashboard-2021-vc-funding-wrap-up). Narratives are changing, but *many investors still consider previous raise experience more important than having bootstrapped a successful company.*

I believe both are important, and *both* should be equally considered.

True, knowing how to raise is vital if you want to capture a massive billion-dollar TAM. So is knowing how to manage marketing, compensation, sales pipelines, schedules, and more (and managing each in a way that bolsters profitable growth). Lessons of the latter are experienced by all who start ventures, but the *pressure* from those lessons falls deeply on the bootstrapped entrepreneur.

In addition, living in a remote-first, post-COVID world has shown that a lack of venture connections doesn’t determine the validity of the founder. [Some funds](https://airtable.com/shrJOYSsuj28MZNsQ/tbleUOoPr3YtgLbWr?backgroundColor=greenLight&viewControls=on) have that ethos built into their DNA by focusing solely on under-represented founders. Others are using shifting market conditions as an opportunity to evaluate their pipelines, and support more founders that dream big *and* have experience building a healthy, profitable, enduring brand—regardless of the startup’s location.

Brian’s thread on this captures that sentiment perfectly:

```cv
tweet
https://twitter.com/BrianBrackeen/status/1345745413584920578?s=20&t=NFuSRO7rUd_06y1Eh1892A
```

A shift towards supporting *founders (period)* vs. blindly supporting *a specific type of already in-network founder* is one I’m excited to see (and one that’s long overdue). Crunchbase recently reported on this change in an article titled, “[Why More VCs May Want To Back Your Bootstrapped Company](https://news.crunchbase.com/startups/bootstrap-or-vc-funding-startups/).” Bottom line: founders with previous bootstrapping experience are desirable in poor markets.

So where do we go from here?

If you’re an investor, consider funding those who have bootstrapped previously. Recognize that what you’re funding is *more than a story,* it’s a *person who can do what they’ve set out to do.* If someone has been successful with zero outside capital or connections previously… why wouldn’t that success translate into something greater with your backing?

If you’re a founder raising with previous bootstrapping experience, get your story tight and your numbers straight. Eliminating options for investors to say “no” by leading with healthy revenues, high growth, and a big vision for the future is essential. You’ve bootstrapped before: you can likely do so again to craft a bulletproof narrative that investors can’t wait to back.

A bias against bootstrapping is a willingness to overlook great people because they don’t fit your preconceptions of what “founders” look like. After all, the world’s next great founder probably won’t come from a deep network of VCs or have an Ivy League degree.

Don’t miss that opportunity.

---

## TL;DR:

Founders with previous bootstrapping experience:

* Are used to abrasive market conditions. 2022 is “just another day” in their world.


* Know firsthand how to steward finances towards a profitable end goal.

* Remember how to *fight* for what they’re building—not just hope and quit when things get tough.

* Are worth backing, because the next great founder likely isn’t emerging from a deep network of VCs.

Why entrepreneurs with previous bootstrapping experience make fantastic venture-backed founders.

Over the weekend, we [shipped a fresh landing page](https://www.basewell.com/) for [Basewell](https://twitter.com/basewellhq) that includes the first public articulation of where we're headed. I'm excited to share our vision on the future of tech, AI, and human performance development:

---

## We believe the future of technology is adaptive.

That means tools will use AI to learn who you are and how you work, and will conform to meet you where you're at; automatically adjusting to your needs vs. forcing you to confirm to a rigid system.

```cv
gallery
{"layout":"hscroll","images":[{"src":"https://firebasestorage.googleapis.com/v0/b/maitake-project.appspot.com/o/pages%2FUEOycrGUM2NGSs8890K0vulFWs73%2FWnQsMgzR2JjnU7KVHpwJ%2Fc0163ea9-35e6-4d19-97f0-513df605b7d4.png?alt=media&token=47bbde94-2936-410e-933d-dcb9f7d49161","id":"c0163ea9-35e6-4d19-97f0-513df605b7d4","width":1988,"height":413,"filename":"linear.png","type":"image/png","caption":"","border":false}]}
```

This shift would be revolutionary.

* Relationships between SaaS products and end-users would become symbiotic instead of linear.

* A hyper-personalized UX would reduce friction (and reduce churn by association).

* Companies would have more accurate data to solve increasingly complex problems.

The hard side of the problem is *adaptive tools don't really exist yet.* It's true terms like "adaptive" have been thrown around before (especially in the context of learning tools), but they've been primarily focused on content recommendations vs. understanding and conforming to user needs.

Netflix—while not a learning tool—is a prime example of this. You've probably heard Netflix [uses an algorithm to change covers based on your viewing preferences](https://netflixtechblog.com/artwork-personalization-c589f074ad76)? That form of "adaptability" is where most current learning tools end: surface-level.

In a more applicable example, say someone receives a low quiz score in a specific subject. Current platforms might make the following recommendation: train more in that subject until the quiz score is higher.

That's it.

Helpful? Maybe. Truly adaptive? No.

```cv
gallery
{"layout":"hscroll","images":[{"src":"https://firebasestorage.googleapis.com/v0/b/maitake-project.appspot.com/o/pages%2FUEOycrGUM2NGSs8890K0vulFWs73%2FWnQsMgzR2JjnU7KVHpwJ%2F4a836637-b32e-4fb1-aafb-a887dc708000.png?alt=media&token=031d098a-c7fe-494f-a990-0798921d7716","id":"4a836637-b32e-4fb1-aafb-a887dc708000","width":1323,"height":465,"filename":"function.png","type":"image/png","caption":"","border":false}]}
```

Critical context is missing to enable true adaptability. Yet unknowing consumers *feel* like things are adapting, because of that automatic content recommendation. It's a *false-positive*: a *negative feedback loop* that costs companies millions.

Wouldn't it make more sense to know if that person is:

* Distracted, or disengaged? If so, why? Where?

* Skipping content or just a fast reader?

* Struggling with complexity, or just a slow reader?

* Comprehending information or just good at guessing quiz questions?

Answering these questions should shift how the platform responds.

Knowing that a user struggles with completing complex, long-form, written content and has high distractibility in lessons more than 7 minutes is crucial. It's impossible to meet someone's needs without that info.

So, off-the-bat there's a LOT you can do when you start collecting that data. Yet, answering those questions is just one side to a more complex network of problems (more complex, in part, because humans are complicated).

The good news? While we're a complicated species, we're are also systematic and predictable. This is especially true in the context of corporate or educational environments, because training is standardized and outputs are measurable.

The question now is, *how do you create software that's truly "adaptive"?* By also learning from human interactions, at scale, across:

* industries

* geographies

* workplace cultures

* societal cultures

* personalities

* departments

and a myriad of other data that may influence how someone learns and produces.

Collecting all that info, you've begun answering an age-old question: "based on who \[person\] is: how they learn, where they work, and what they're expected to produce, how might their training experience be optimized to perfectly suit their unique circumstances?"

```cv
gallery
{"layout":"hscroll","images":[{"src":"https://firebasestorage.googleapis.com/v0/b/maitake-project.appspot.com/o/pages%2FUEOycrGUM2NGSs8890K0vulFWs73%2FWnQsMgzR2JjnU7KVHpwJ%2F073acbda-6656-4ed3-94ac-0a96568801d8.png?alt=media&token=536f8a78-834b-4241-925d-2845221fbb74","id":"073acbda-6656-4ed3-94ac-0a96568801d8","width":2125,"height":1593,"filename":"person.png","type":"image/png","caption":"","border":false}]}
```

Current learning tools don't gather that info. Instead, they track unhelpful metrics like *progression*, *recent quiz scores*, and *when content was completed*.

> How do you expect to fully understand your team's strengths and weaknesses if the context of who they are, what they've learned, and how they work, is missing?

Knowledge around how your team operates is your company’s most important data. Limitations to gathering those insights leave you with blind spots, waste, and in false-positive: a critically dangerous—sometimes lethal—combination. It's no wonder [undertrained & disengaged employees cause $398B every year in waste](https://www.gallup.com/workplace/236552/managers-engaged-jobs.aspx).

With all that in mind, you might ask, *"why does this problem still exist?"*

Well, to be frank, the solution is really damn hard (not to mention out of scope for most companies). In order to start *solving this problem*, platforms must be equipped to collect, model, and train from critical customer data (surprise: *current tools aren't engineered for this).*

In addition, *AI must be used for more than novelty*. Building truly adaptive technology is more than streaming a return statement back from OpenAI's API. You must rigorously collect, build, and train (your own) models from (your own) proprietary information.

That's where [Basewell](https://www.linkedin.com/company/basewell/) comes in.

```cv
tweet
https://twitter.com/BasewellHQ/status/1673764160054632465?s=20
```

While we're providing best-in-class learning tools to seamlessly create, distribute, and measure training content, we're also collecting proprietary data to learn, predict, and model how people are solving problems on a global scale. True adaptability is born out of that effort.

Furthermore, *true adaptability is impossible to achieve if you're not collecting that info to begin with*. (That's one of the reasons for my belief that data is the ultimate moat of the next decade.)

```cv
tweet
https://twitter.com/heyecs/status/1659303418559692803
```

Knowing how a:

* \[person\] with \[individual attributes\]

* working in an \[industry\] with \[industry attributes\]

* utilizes \[training\] with \[training attributes\]

* to produce \[outcomes\] measured in \[specific ways\]

on a global scale brings insights never available before. That level of intelligence allows you to do some incredible things:

### **1. Create a *truly adaptable* platform (one that's sensitive to the needs of—and reflexively adjusts to—each user).**

```cv
gallery
{"layout":"hscroll","images":[{"src":"https://firebasestorage.googleapis.com/v0/b/maitake-project.appspot.com/o/pages%2FUEOycrGUM2NGSs8890K0vulFWs73%2FWnQsMgzR2JjnU7KVHpwJ%2F4200ab53-d122-4930-a8f8-0044b9e7d6b7.png?alt=media&token=501039d2-c65f-4b36-9487-16ebccee21b3","id":"4200ab53-d122-4930-a8f8-0044b9e7d6b7","width":2360,"height":1156,"filename":"Basewell-flow.png","type":"image/png","caption":"","border":false}]}
```

### **2. Help companies better understand and support their people.**

Using anonymized insights gathered across every interaction, Basewell AI will tailor the learning experience to each person.

That means your future employees never start from zero. 😉

```cv
gallery
{"layout":"hscroll","images":[{"src":"https://firebasestorage.googleapis.com/v0/b/maitake-project.appspot.com/o/pages%2FUEOycrGUM2NGSs8890K0vulFWs73%2FWnQsMgzR2JjnU7KVHpwJ%2F4463e7df-b1ef-4fac-b640-e4274bcfd797.png?alt=media&token=94380626-f27e-419c-85da-bd8a5a535cd3","id":"4463e7df-b1ef-4fac-b640-e4274bcfd797","width":3361,"height":2066,"filename":"network.png","type":"image/png","caption":"","border":false}]}
```

### **3. Build the world's most powerful store of intelligence around workplace human performance development.**

Knowing how factors across people, content, and organizations affect teams and outcomes carves a path to build optimized solutions to uniquely complex problems.

Learning tools are the perfect stage for this thesis, as transferring company knowledge is one of the most measurable rituals in the world.

*All employees train and are expected to produce.* Magic happens when you capture the context before, during, and after those learning moments.

We're building a future where tools can empower—not encumber—users. Where your world is optimized to meet your needs, and where your ability to learn and produce doesn't boil down to rigid, bloated, outdated standards.

---

Basewell is in beta, yet we're already serving incredible companies all around the world: capturing tens of thousands of monthly interactions (making content, training, reporting) from a wide-range of organizations from early-stage startups to enterprises with massive teams.

We're proving people are ready for the age of specialized, personalized tooling that's *beautifully designed, doing obvious things well*, and *using AI in an approachable way* (ie: under-the-hood vs. rubbing AI in your face).

My call to action is simple: if you believe in this vision, *join us*. Be a part of building the future. You can use Basewell right now to create, distribute, and measure beautiful training content. (Not to mention beta companies will be the first to access AI-powered adaptability when it launches).

If you have questions or want to talk shop, my DM's are open. For everything else, be sure to check out [Basewell.com](https://www.basewell.com/) (or [follow on LinkedIn](https://www.linkedin.com/company/basewell) or [𝕏/Twitter](https://twitter.com/basewellhq)) to follow along.

A vision on the future of tech, AI, and human performance development

Back in 2019, [Arvind Narayanan](https://twitter.com/random_walker) presented a simple statement on the popular startup/developer forum [Hacker News](https://news.ycombinator.com/item?id=21224209) that kickstarted quite a bit of conversation: "why enterprise software sucks." The replies were, of course, full of hearty passion and general disdain for how utterly terrible enterprise software experiences are.

And you know what? They're absolutely right. Enterprise software sucks. Everybody knows it, but it's been accepted as just "one of those things" that we hope will get better with time. "The next person will take care of it," people think, as they sip their stale coffee and type away in a UI that was invented for Windows 98, in a company still hanging dusty "employee of the month" photos on the wall and calling it culture.

All in all, enterprise technology has been really slow (actually glacial) to adopt new demands in consumerism: specifically the trend toward clean, simple, one-touch solutions that take the guesswork and [bloat](https://en.wikipedia.org/wiki/Software_bloat) out of the user experience and tech stack.

One would argue that this issue of hellish business software stems from a disconnection between the **actual** B2B consumer and the **non-professional** consumer: it's no secret that individual consumers have preferences, but businesses have needs! Build the software to solve the needs of the business and you have a winner... right?

Two decades ago this strategy worked beautifully. Today, it's wrong.

You see, in a "work from anywhere" world, the lines are getting continually blurred between a person's labor and lifestyle. Work is no longer that annoying chore you must chip away at, but simply an increasingly intertwined part of life—the thing that's never quite put away in your moments of rest, and that never quite felt the same after March 2020.

Accelerated by this ideology is the concept that business software doesn't have to suck any more. B2B SAAS can, in fact, be beautifully designed, simple to integrate, and delightful to use—all without sacrificing the core need of the software in the first place: solving a niche, often overlooked and underdeveloped issue that's dramatically impacting the bottom line.

In my opinion, founders and product designers pioneering the next wave of B2B SAAS technology should focus their initial efforts on three areas:

1. **UI/UX simplicity**

2. **Ease of software adoption**

3. **Seamless and direct integration into modern professional tech stacks**

Let's dig into the specifics as to why.

## Worldwide spending spree on enterprise technology

Identifying business tech trends isn't rocket science. For this conversation, we're going to look at two data points:

1. **Where** money is currently moving in B2B SAAS spending (trends, areas of focus, what's driving decision-making)

2. **How** that money is being directed once a decision to spend has been made (that is, what drives the ultimate decision between competitor A vs. competitor B?)

According to [PwC's 2021 CEO Survey](https://www.pwc.com/gx/en/ceo-agenda/ceosurvey/2022.html), 84% of CEOs plan on investing moderately to significantly in their corporate tech stack (with the majority of that expenditure in digital transformation products, followed by cyber security). But unlike previous years, we're seeing a dramatic trend toward businesses using their technology to adopt a partnership mentality over just a customer mentality.

This might look like a slight—potentially even meaningless—change in buying habits, but the reality is that today's businesses are purchasing with dramatically different standards than before COVID.

Right now, companies are strongly prioritizing a blend of **cost-effectiveness** (the savings from automating potentially inefficient tasks); **workforce stabilization** (maintaining productivity and efficiency in a hybrid or completely remote model); **symbiotic partnerships** (both the tech and the business are better because of their relationship); and **achieving better outcomes** in a cheaper, more sustainable manner.

What does this mean for your new B2B technology startup? **If you cannot clearly and definitively prove how your tech achieves each of these four goals, your customer can't either, and you will lose long-term in the market.**

It's a fallacy that much of the world successfully went remote in 2020: the truth is that people just went home.

Companies were left needing to solve increasingly complex problems with a decentralized workforce, and now have the added challenge of doing so with technology that's built to enhance—not encumber—the lives of their employees away from their desks. Put in layman's terms: *a remote workforce will not thrive on technology that's just built to solve a core business need. Now more than ever, enterprise SAAS startups must consider the **context**, not just the core **purpose**, of their product's use.*

The term context refers to the more ambiguous aspects surrounding enterprise SAAS applications: factors such as a positive impact on the quality of an employee's work life, and sustainability in a decentralized infrastructure. Purpose refers to what SAAS founders have traditionally considered: factors linked to the software's [product-market fit](https://pmarchive.com/guide_to_startups_part4.html).

## Purpose of B2B SAAS

As mentioned above, enterprise software founders have always needed to answer several fundamental questions about the purpose of their SAAS:

1. **Technology:** Does your software efficiently integrate into the business's current tech stack? Is your SAAS duplicating previous solutions the business might have already solved?

2. **Workforce:** Does your software help upskill a workforce, positively impact culture, or help the business retain talent?

3. **Scalability:** Does your software break at a certain level of scale or depth of implementation?

4. **Governance:** Is it your software company or the end client who ultimately controls the data, privacy, and security of the software?

## Modern context of B2B SAAS

Several new and crucial challenges have emerged since March 2020:

1. **Technology:** What specific feature would make the end user want to continue using your software when they're not in the physical office?

2. **Workforce:** Are you able to clearly define how your SAAS brings a positive impact to the quality of work life for the end user and not just increased productivity measured against their KPIs? To what degree does your SAAS support a widely decentralized workforce?

3. **Scalability:** In addition to not breaking at scale, does your SAAS properly serve the needs of a large national—or in most cases—international talent force? Are regional- and location-based bottlenecks present?

4. **Governance:** Since most enterprise SAAS outsources their server and data-handling demands, how are you ensuring the protection of professional data if you're contracting those services out to a third party?

## A generational shift is coming

In addition to these considerations, a more subtle underlying expectation is creeping into businesses—some have noticed, but many have not. That is, the technology expectations of the most tech-savvy generation the world has ever seen: GenZ. If you own a company and aren't considering GenZ's expectations in your growth/employment strategy, you're already losing. In fact, GenZ will make up approximately 27% of the workforce by just 2025... the time is now to adjust for this new wave of talent.

According to a recent [Dell finding](https://www.dell.com/en-us/dt/perspectives/gen-z.htm), 80% of GenZ professionals aspire to work with cutting-edge technology, and as much as 91% of interviewed GenZ stated that a business's tech stack would influence job choice among similar employment offers. *SAAS companies that overlook GenZ's revulsion toward boomer tech will wither and die in today's market.*

Cathy Hackl, in her recent [Forbes article](https://www.forbes.com/sites/cathyhackl/2020/09/07/gen-z--the-future-work--play/?sh=23a380fb142e) outlining the relationship GenZ has with their technology, brought to light more futuristic—yet still relevant—thoughts around this subject, by extending the conversation into [Web3](https://www.odysseydao.com/articles/what-is-web3) and the metaverse. Oh yeah, that "crypto" thing you've been hearing about? It's kind of a big deal, and GenZ is *all over it.*

Just look at Walmart's latest jump into Web3 with [Walmart NFTs and a Walmart Metaverse](https://decrypt.co/90747/web3-founders-welcome-walmart-nfts-metaverse), or how Adidas continues to dominate in virtual worlds like [Decentraland](https://decrypt.co/resources/a-3-minute-guide-to-the-new-digital-world) with [collaborative virtual projects](https://www.one37pm.com/nft/fashion/adidas-continues-to-innovate-into-web3-with-nft-collaborations). If you thought virtual currency, NFTs, and the metaverse were just fads, think again.

Now I'm not implying that you need to stop accepting fiat currency and start minting NFTs of animated shoes with your company logo, but I am bringing to light a very important shift: the world is moving toward immediate adoption of new tech, instant shifts in global markets, decentralization, and remote-first connection. Adaptable, consumer-friendly enterprise technology is going to be dramatically relevant within the next few years.

## The bottom line

Many conclusions can be drawn about how the future of work will look amidst an increasingly global and decentralized workforce... I'm of the belief that it's impossible to truly predict how exactly things will play out. Yet I am confident in certain predictions, based on the simple math of where the current data falls:

> *CEOs are spending more on tech than ever before + most B2B tech options are crap + GenZ cares—A LOT—about their work tech stack = perpetual issue/disaster waiting to happen.*

As a starting point, I recommend asking yourself the following questions:

**How does our SAAS provide a relevant solution without adding any unnecessary steps to our UI?** *The fewer steps you have to add to your SAAS, the better.*

**If our software wasn't built for businesses, would it fit in as a consumer app?** *Audit your design to test the friendliness and stickiness of your app with "work from anywhere" consumers.*

**Would a non-professional consumer be able to navigate our software without issue?** *Audit your software's ease of use.*

**Are we prioritizing function or design?** *You should have a balance between both.*

I'm a believer in running to where the world is going—not staying cemented in where it's been. But the difference between aimless wandering and deliberate pursuit is **focus**.

This year, let's direct our focus toward the systems that affect every facet of our lives. By prioritizing simple, beautiful enterprise technology, B2B SAAS founders have an opportunity to make even the most mundane aspects of one's work a little more enjoyable; help companies retain top talent; and positively impact the professional lives of millions of people.

That's a future of work that works for everyone.

Emerging Enterprise Tech Looks More Like Your Favorite Consumer App Than a Niche Business Solution—and That's a Great Thing

Co-founder, CEO at Basewell

How Compass’ Falling Stock Represents a Greater Issue in Today’s Market

Best Real Estate Agent

Recognized as one of the top real estate professionals in Dallas, TX for 2018 industry achievements.

Top Residential Real Estate Producer

Responsible for front-end engineering and product design alongside responsibilities as CEO.

Basewell

Designed and developed the visual identity and landing page for the MedTech startup, Glucolight.

Determined how to communicate complicated medical solutions in a consumer-friendly, clear way, while simultaneously navigating regulatory red-tape.

Visual Identity

A beautiful way to write and share long-form thoughts on Twitter.

Raft was a scheduling tool to draft, share, and analyze Twitter threads. Focused on simplicity, designed in Figma, and written in Swift/SwiftUI.

Raft

A community cooking app for creating, editing, and sharing recipes with friends. Utilizing a full-screen, TikTok-like social feed and community features like a native commenting and rating system.

Designed and prototyped with Figma, developed with Swift/SwiftUI.

Olive

Volunteer

(2014 - 2015)
Founded Stewart Residential under broker Ebby Halliday, REALTORS®. Grew to a company-wide top producer.

(2015 - 2016)
Merged with another top agent to build RUECKERT + STEWART, one of the highest-grossing sales teams in the company.

Founder - Stewart Residential

Consulted with tech and tech-enabled startups in the USA & Canada. Helped grow multiple startups from post-idea → millions in ARR.

Towards the end of this consultancy sprint, I explored the thesis that became Basewell with market research, customer conversations, and MVP product design/development.

Founder

(2016 - 2018)
Merged the RUECKERT + STEWART Group with the Compass brand to continue tech-forward expansion.

(2018 - 2019)
Split the RUECKERT + STEWART Group and re-established Stewart Residential (still with Compass). Was awarded as a top Dallas agent with annual business upwards of $30,000,000.

Stewart Residential was later acquired by a Compass associate broker.

Started in real estate as a buyer's specialist for Dallas residential property.

Real Estate Agent

Building AI-powered, adaptive learning tools.

Evan Stewart

2023

2022