What’s the economic reality of betting years of your life on a startup? For most founders, it’s not the overnight success you hear about on LinkedIn or TechCrunch.

For me, that reality meant an average annual salary of just $54,700 over 7.5 years, leaving more than $1.2M on the table in opportunity cost.

To give you a baseline, our startup was admitted to Techstars. We raised $2.4M over 7.5 years and peaked at about $50k in monthly recurring revenue.

Here’s what that meant for my personal earnings over that period:

• Years 1-2: $0
• Years 3-4: ~$50,000/year
• Years 5-6: ~$80,000/year
• Year 7-7.5: ~$100,000/year (before dropping back to zero at the end)

My total earnings over 7.5 years were roughly $410,000.

Now, let’s compare that to a more conservative corporate path I could have taken, going into product management, growth, or any number of other functions:

A conservative estimate:

• Base Salary (7.5yrs): ~$1,150,000
• Stock/RSUs: ~$400,000
• 401k Match: ~$60,000
• Total Comp: ~$1.61 Million

An aggressive (but still realistic) estimate:

• Base Salary (7.5yrs): ~$1,400,000
• Stock/RSUs: ~$700,000
• 401k Match: ~$70,000
• Total Comp: ~$2.17 Million

When you subtract my actual startup earnings (~$410k), the direct compensation gap lands between $1.2M and $1.8M.

But that’s not the full economic cost. Looking at the S&P’s returns from that period, the missed compound interest on that unearned cash adds another $450k to $600k to the total.

That brings the full economic cost of my 7.5-year journey to somewhere between $1.65M and $2.4M.

I assure you, this isn't intended to be a sob story. It’s just the statistical reality for the vast majority of founders. Studies show around 90% of startups fail, and far fewer actually produce life-changing financial outcomes. Remember, just because a startup doesn't "fail" doesn't mean you're thriving.

If you're a founder reading this, hate to say it, you’re likely making a similar financial sacrifice, whether you’ve run the numbers or not.

Look, I'm not saying you shouldn't do a startup. I just think founders (and startup employees alike) should acknowledge that your grit and determination aren’t infinite resources. The goal isn’t to bleed for a decade (or 75% of one, in my case) to prove a point. It’s to get to an answer (“Is this working or not?”) as QUICKLY as possible. Or GTFO.

What I'd Do Differently (With Hindsight)

With the benefit of hindsight and a lot of expensive lessons, here is a long list of things I would do differently.

Before we dive in, a disclaimer: these recommendations are just things I would keep in mind, given my personal experience. These aren’t universal rules. For nearly every recommendation below, you can find a famous example of a successful company that did the opposite. And if you’re currently doing something I say I’d never do again, it doesn’t mean you’re wrong.

This is about stacking the odds in your favor. My belief is that the more of these you get right, the smoother your path will be. The more that are working against you, the steeper your uphill battle.

1. Learn on someone else’s dime first.

After about a year at Deloitte Consulting, I left to start my company. If I could do it again, I probably would have explored joining someone else’s startup first. Specifically, a company that had already raised a sizable seed or Series A round, so they have traction and resources. I think I could have learned some core startup skills, gotten my hands dirty on a lot of different problems, and seen what an early-stage company is like from the inside, without incurring a ton of risk. Oh, and all while getting paid close to market rate (so I can invest some of it and let the earnings compound) and maybe I'd even get a little equity upside.

Who knows, joining another startup might have even scratched the entrepreneurial itch enough that I wouldn't feel the urge to start my own company.

2. Solve a problem you’ve actually lived.

I co-founded my startup with my brother while he was in his residency to become an interventional radiologist. He was the one living the problem we decided to tackle; I wasn't. That second-hand understanding turned out to be a major blind spot. Because I didn’t experience the problem myself, I couldn’t foresee the high regulatory burden, I didn't understand the unit economics of healthcare well enough to know we were fighting an uphill battle, and frankly, I couldn’t see that we were building more of a “vitamin” than a “painkiller.”

Yes, you'll hear stories about how industry outsiders sometimes make the best founders because they aren't jaded by long-held beliefs, but I'd bet that 9 times out of 10, you're better served by DEEPLY understanding your space.

3. Don’t quit your day job without real validation.

I would hesitate to leave a stable W-2 job again without either a convincing number of paying customers OR a solid cohort of users who are repeatedly using and benefiting from my product. Instead of jumping in headfirst, I would launch an analog product or a “wizard-behind-the-curtain” service/minimally viable product while still employed. Ideally, I wouldn’t make the leap until my side gig was actually cash-flowing, to further de-risk the leap.

4. No part-time co-founders.

My brother was incredibly dedicated, pouring an insane amount of time into the company on top of his medical training (I still don’t know how he did it). That said, I found that startups demand an unreasonable, all-in level of commitment from their leaders, and our unconventional co-founder dynamic had real consequences. We could only meet at awkward hours, which slowed down our decision-making. It also meant we had one less hands-on operator to manage the day-to-day of the business.

5. Treat cash or real usage as the best indicators of traction.

Early on, I mistook positive sentiment and verbal commitments from customer interviews as a strong validation signal. I'd soon learn that real validation is not someone smiling and nodding during a sales call; it’s a cash transaction, a contractual Letter of Intent, or a signed design partnership where the customer has real skin in the game. Most people are nice and will hesitate to give brutally honest feedback, especially when a founder is passionately pitching a vision of a future that doesn't yet exist.

A quick note on validating with a free product:

In the hunt for validation, you’ll often hear that you shouldn't give your product away for free. My take is that it can be a powerful test. If you offer it for free and people use it and love it, that's a great signal. Now your job is to see if they'll pay. But if you offer it for free and get no adoption, that’s a major red flag that the problem isn't painful enough, or you’re not solving it in the right way.

6. Resist raising money for as long as possible.

Looking back to 2016, maybe it was the books I was reading or the podcasts I was listening to, but when I founded my company, I was infatuated with the venture and startup world. I saw fundraising as a way to boost my ego and prove we were on the right path. I’ll never forget getting the call that we’d been accepted into Techstars; a part of me genuinely thought, “This is working...How can we possibly fail?” Turns out fundraising can be a false validation signal too. Moreover, it’s massively time-consuming and can add immense pressure, cloud objective decision-making, and make it psychologically harder to walk away when things aren’t working.

7. Put a clock on your efforts.

If I did raise, I’d be explicit with investors from day one: “I’m giving this 12–18 months. If we haven’t found meaningful traction, there's a chance we'll shut this down. How does that make you feel?” That level of transparency will help alleviate the sunk-cost pressure to “just keep going.” I would also openly talk about the very likely down-case scenarios where the business goes to zero. If I sensed my investors were blinded by the potential upside, I would keep pressing until I knew they truly understood the risk they were taking.

My only negative investor experience came from breaking this rule. I took a $50k check from someone I never met, without having the brutally honest discussion mentioned above. Because we never aligned on expectations (and they never got to know me as a person, see how hard I worked, or understand how much I cared), they were furious when the investment didn't pay off, despite their personal net worth of nearly $500M.

8. Be intellectually honest about product-market fit and friction.

If customers aren’t pulling the product out of your hands, you might not be solving a painful enough problem, offering it in the way your buyer wants, or making it easy enough for them to adopt. That friction you feel is almost always a signal that one of your core foundations is shaky. It could be a sign of poor product-market fit, a weak market-model fit (your pricing is wrong for your market), or even a broken channel-model fit (you can't profitably reach your customers).

We talk about the concept of the "Foundational Five" at length in the Demand Curve Growth Program. The first time I was introduced to the Foundational Five framework, it gave a name and structure to the headwinds I had fought for years. It’s a solid framework, and one I’d encourage any founder to run their business through to make sure they aren’t swimming upstream from day one.

9. Make sure your niche is big enough.

Niching down is great because it allows you to focus on solving ultra-discrete problems better than other generalized solutions that dabble. But it also shrinks your market size. Sometimes it's easy to forget that not all niches are created equally. As you narrow your focus, do a quick market sizing to ensure your Total Addressable Market (TAM) is still large enough to support the kind of business you want to build. My business ended up in a very small niche that was hard to scale out of.

10. Build a business with healthy margins.

High-margin businesses are a superpower. They allow you to spend more on advertisements to acquire customers, reach profitability faster, reinvest in growth, and hire better talent. They increase your margin for error. The business I started ended up being lower margin than we thought it would be, which made it difficult to reinvest in growth and expand into new service lines. Wouldn't recommend starting a business that you know will have low margins from the outset.

Psst...the quickest/easiest way to improve your margins is to increase your price 😉.

11. Confirm a reliable channel to your ICP exists.

Before you build, I'd pressure test whether there are a few (more than one) reliable, scalable channels to reach your core customers. For us, interventional radiologists ended up being pretty hard to get in touch with. They’re on LinkedIn, but not as frequently as business folks. They’re too small of a group to target effectively on Meta. You can reach them through platforms like Doximity, but adoption amongst the community was still low. We found that word-of-mouth and specialized medical conferences were the way to go, but admittedly, we unlocked conferences too late in the game with too little cash (and stamina) in the bank.

12. Start with a small, effective feature set (not a platform).

Sometimes it can be tempting to build a grand, comprehensive tool from the outset. Yes, there are examples of companies that have done this (Attio CRM comes to mind), but I'd personally resist that temptation. Instead, I'd isolate the smallest possible feature set that can provide 10x value to a user. I'd validate that minimal feature set quickly, get it into people's hands, learn from their usage, and only then expand into a platform over time.

13. Optimize for short sales cycles early on.

Our first idea involved selling to enterprise hospital systems, which meant 12-18 month deal cycles. It took forever to get feedback and learn if what we were doing was even working. If I were building a B2B company today, I would start in the SMB or mid-market space to get rapid feedback from customers, accelerate learning loops, and secure early wins before attempting to move upmarket.

14. Avoid business models where value is out of your control.

Here's what I mean, I would never build another lead-gen company (sorry if you're reading this and you have a lead-gen company). The model is brutal because the value your client receives is entirely dependent on their ability to close the leads you provide. If their sales team is slow or ineffective, your product is perceived as worthless, even if you delivered perfectly qualified leads.

Lead-gen companies are just one example of businesses where the ultimate value is out of your control. Think about two-sided marketplaces, where your platform's value depends on the quality of third-party users. Or a sales coaching platform designed to improve a rep's pitch, where the tool's value is completely dependent on the rep actually using it, internalizing the feedback, and changing their habits over time. In all these cases, you can do your job perfectly and still get blamed when the customer fails to get a return.​

If/when I do it again, I'll build something where value is delivered directly by the product itself. Which leads me to my next recommendation...

15. Provide unambiguous, self-evident value.

The faster you can prove your value, the faster you can build momentum. I would avoid businesses that require long, drawn-out pilots or multi-month trials to prove a complex ROI. I’d much rather build something where the value is immediately apparent and experiential. For example, let's say I was building a new document editor software where the selling point isn't some complex business case quantifying hours saved by employees who use it. Rather, someone who uses the tool has the simple, qualitative feeling of, "I just prefer this experience to Google Docs." That kind of self-evident value can shorten the path to testimonials, social proof, and word-of-mouth growth.

To be clear, I'm not encouraging you to avoid building a business on a quantitative outcome like time saved or revenue gained (most great businesses have some quantifiable business case). But if you go that route, I'd just make sure the value is both undeniable and highly reproducible. Marginal improvements (a slight time savings, a few more closed deals, single-digit percentage points of increased revenue, etc.) may not be a strong enough value prop to scale. That’s the kind of value that gets challenged during sales calls, debated during renewal calls, and cut from the budget when things get tight.

16. Drastically shorten the ‘Time to Value’.

Here's an observation I've had about momentum: when a customer can feel the impact of your product in hours or days, not months, it creates a powerful tailwind for growth. The faster you can get someone through the loop of seeing a demo, trying the product, and having that “aha!” moment, the sooner they start telling their friends and colleagues. That speed drastically shortens the time it takes to get case studies to socialize with other prospects.

This isn't to say you can't build a business where it takes a full quarter to see meaningful results - many huge companies operate this way. It just means you're choosing a more resource-intensive path. That journey typically requires more coordination, more hands-on change management, and a larger support team to ensure your customers get the value you promised.

17. Productize a known, analog behavior.

From the perspective of de-risking your entrepreneurial journey, I get excited by ideas that aren't totally new 'inventions.' Rather, you can find a problem people are already using some workaround to solve, and productize it. The opportunity is simply to package that existing behavior into a better, easier, more seamless solution.

A great e-commerce example is the Squatty Potty. For years, people were using a clumsy workaround (stacks of books or a random stool) to elevate their feet for a more natural position on the toilet. The company simply took that exact DIY behavior and created a purpose-built, branded product to solve the problem perfectly.​

You see the same pattern in software. Loom is a good example. Before it existed, users needing to explain a complex issue visually would use QuickTime Player to record their screen, save the large file, wait for it to upload to Google Drive, and then finally send a link to a team member. The process was slow and ate up both local and cloud storage. Loom took that exact behavior and made it seamless, productizing the entire workflow so you can record and share instantly with a single link.

The Bottom Line

I want to end by saying that startups are an amazing thing. They are a core part of our economy and, in many ways, the "American dream." On a personal level, some of those 7.5 years were the best of my life. When you're truly locked in on solving a problem you're passionate about with team members you enjoy being around, the process can be insanely fun. There's real joy in the journey.

But I also believe it's important to step back every six months or so and have an honest conversation with yourself, your co-founders, and your spouse (hell, talk to ChatGPT for all I care) about the following things:

• Is this still serving me and my family?
• Am I still having fun? Am I enjoying my life and the work I'm doing?
• Are we being objectively honest about our traction and the validity of this idea?
• Is there real upside here?
• How long will it take to achieve?
• What are my alternatives, and what is the real cost of continuing down this path?

Answering those questions clearly is the goal. I personally think frameworks like the ones we teach in our Growth Program can help you get there faster, but the tools you use are less important than the conversation itself.

If this story resonated with you in any way, feel free to reach out. I'm always happy to chat with other founders who are in the thick of it. I promise, you're not stuck. ❤️

​Kevin DePopas​
​Demand Curve Chief Growth Officer

Appendix:

My 7.5-Year Startup Journey (TL;DR Version)

The First Idea: Sway Health (Preventative Counseling at Scale)

We started with an ambitious idea that got us into Techstars: an enterprise software that integrated with hospital EHRs that would scan patient files for untreated behavioral conditions, generate an evidence-based counseling session personalized to a patient, and automate the use of preventative counseling billing codes.

• Why It Failed: The sales cycle into hospitals was 12-18 months. The revenue per counseling session was minuscule compared to other lucrative procedures. And most importantly, the problem wasn't a painkiller for physicians; our software added clicks to their already-packed workflows/schedules, so pilot utilization was abysmal. The time to results to prove efficacy was long.

The Pivot to a Marketplace: Pain Theory → Helped

Because enterprise was so slow, we built a direct-to-consumer arm of our preventive counseling tool, which taught us how to target patients via advertising and build intake technology. Doctors suggested a higher-margin use case: using our tech to find them qualified candidates for niche medical procedures. This led to our first major pivot. We rebranded to Pain Theory, a marketplace to connect patients with pain specialists. After raising a couple of bridge rounds, we rebranded again to Helped, raising a $1.8M seed round to build a broader specialist marketplace.

• Why It Failed: Building a two-sided marketplace is expensive. If we wanted to do it right, we'd need to raise a lot more money to build awareness on both the supply (doctor) and demand (patient) sides, and we would have had to subsidize low margins for years. We also ran into the legal complexities of pricing a healthcare marketplace due to anti-kickback statutes, meaning we could only charge pennies on the dollar for the value we were creating for doctors.

The Final Pivot: The Tech-Enabled Service

We saw that thriving D2C healthcare businesses like Hims and Roman used the same playbook: attract a patient with an ad, qualify them with an intake funnel, schedule a telehealth session, nurture nurture nurture until the patient decides to purchase a product. With the existing technology and expertise we had built up over the years, we decided to offer this entire playbook as a service for small- and medium-sized practices, enabling interventional radiologists and interventional pain specialists to implement similar intake funnels to Hims and Roman. We handled everything from ad creation and campaign management to building their intake flows and having our care coordinators text and call patients to coordinate scheduling. This was the business that got us to $50k in MRR.

• Why It Failed: Even with positive ROI, most procedural specialists aren't used to acquiring patients via paid media; their businesses are largely referral-driven, which resulted in their willingness to pay being lower than expected. To get them results, we had to take on more and more of the operational work (from lifecycle marketing to hands-on patient management) which made our service more expensive than doctors were comfortable paying. The concept of spending 20-30% of a patient's LTV on acquisition was foreign to them. And again, pricing can be really challenging in a regulatory healthcare environment. The time-to-value was still slow (~4 months to prove ROI). Even so, I'm incredibly proud of the impact we made. We connected countless patients with minimally invasive alternatives to surgery they never knew existed and delivered a scheduling experience that was second to none. But alas, the business began to look more like a non-scalable agency than a tech company, so we decided to shut it down.