The 3AM Question Every Founder Faces: Is It Time to Walk Away?

And The Four-Pillar Framework That Saved Me From Quitting Too Soon

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We're here to demystify entrepreneurship and make it more accessible to all. Before we dive in to today’s topic, my next live office hours/AMA is tomorrow, Wed., May 21st at 10am PT. Upgrade your sub to $10/mo level to join and bring your questions!

Today, I want to talk about something every founder faces but few discuss openly: those moments when you seriously question whether you should quit.

The Brutal Truth About Building a Company

Building a company from nothing is hard. Brutally hard. There will be many moments when you'll ask yourself if you should keep going.

It's a valid question. In fact, it's one you should ask regularly.

No one starts a company planning to quit. We launch with visions of success, impact, and maybe an exit. But sometimes, the smartest move is to walk away. The question "Should I keep going?" will haunt you more times than you'd like to admit. It's not weak to ask it—it's wise.

When I was building Boardroom Insiders, I had many moments of doubt. Sometimes they came after a crushing rejection from a prospect we'd spent months pursuing. Or they emerged during the middle of the night when cash was tight and I wondered if I would ever be able to pay myself so I could quit my day job. And they even came unexpectedly in the quiet aftermath of celebrating a new milestone of success, when the weight of responsibility would suddenly hit me: dozens of families now depended on decisions my partner and I would make. Their mortgage payments, their children's braces, their retirement plans—all connected to our ability to keep this dream alive.

The problem isn't having these doubts and fears—that's completely normal. The problem is how we manage them when they arrive.

One should never make life-altering decisions from a place of fear, exhaustion, or crisis. Why? Because our darkest moments are precisely when our judgment is most compromised.

Instead, you need predetermined rules of engagement for wrestling with these thoughts—a framework that stands firm and independent of your emotional state. Had I made decisions based purely on how I felt during those 3AM panic sessions, I would have walked away from what ultimately became a magical decade of building Boardroom Insiders, growing a phenomenal team, and eventually achieving a $25M exit.

Your future self deserves better than decisions made by your most frightened, exhausted self. You need a process—a framework that brings objectivity to what feels like an entirely emotional question.

That framework is what saved me, and it might just save you too.

The Four Support Pillars Every Entrepreneur Needs

Through my own journey and watching hundreds of other founders, I've identified four critical groups whose support can make or break your business. Your success depends on having solid backing from at least two of these groups—and one of them must be customers, or you need to pivot.

1. Funders Who Believe in You Enough to Write Checks

Funders aren't just venture capitalists or angel investors. They're anyone willing to financially back your vision:

• Traditional investors

• Friends and family

• Customers who prepay

• A spouse who supports the household while you build

• Even yourself, if you're investing savings or going without a salary

At Boardroom Insiders, we had three angel investors who were also seasoned entrepreneurs. They believed in us enough to write checks when we were just getting started. Their financial support was crucial, but their emotional support and business advice were equally valuable.

Pro Tips: Don’t take money from anyone who can’t afford to lose it; and try to find investors who are seasoned entrepreneurs themselves, as they bring hard-earned wisdom, as well as money, to the table.

2. Industry Leaders Who Validate Your Vision

These are the people with credibility in your industry who are willing to vouch for you:

• Respected peers who evangelize your solution

• Industry influencers who spread the word with their audiences

• Partners who choose to integrate with your product

• Advisors who open doors to opportunities you couldn't access alone

• Former colleagues who actively send business your way

This pillar was challenging for Boardroom Insiders. While we had a small group of industry veterans who believed in our vision, the broader industry either ignored us or viewed us with skepticism. Why? Because we were swimming against the current.

At a time when "data scraping" and "automation at all costs" were industry imperatives, we built a business centered on human research and curation. Our market wasn't massive enough to attract venture capital, and our approach wasn't "scalable" by Silicon Valley standards.

But here's what I learned about industry insiders: they often have collective blind spots. They're so immersed in current paradigms that they miss emerging needs. As a consultant who had tested all of their tools with my clients, I had seen firsthand how they repeatedly failed to deliver what customers actually needed—which is why I created Boardroom Insiders.

The lesson? Sometimes limited industry support isn't a sign you're on the wrong track; it's a sign you're early in addressing a need others don't yet recognize. That said, if you're getting zero validation from industry experts, it's worth examining whether you're truly seeing something others miss, or if you're the one missing something fundamental.

3. Paying Customers Are Your Strongest Signal

This pillar might seem obvious, but it bears emphasizing: customers who vote with their wallets provide the most meaningful validation possible:

• Early adopters who take a chance on your MVP when it's far from perfect

• Repeat customers who continue to buy despite having other options

• Clients who expand their relationship with you over time

• Users who actively engage with your product and provide feedback

• Customers who voluntarily refer others to you without incentives

At Boardroom Insiders, our customers were our North Star—the clearest signal that we should keep going when doubt crept in. They stuck with us through conditions that would have sent most users running.

They forgave our initially hideous, clunky user interface. They didn't abandon us when we had virtually no usage analytics to show if their teams were even using the product. They patiently waited while we built database records from scratch because what they needed simply didn't exist in our system yet.

Why such extraordinary patience? Because we solved a genuine pain point that they couldn't address anywhere else without significant effort and expense. Our customers weren't just buying a product—they were buying a solution to a problem that genuinely hurt.

Over the years, as C-suite selling became increasingly critical in the tech industry, what we provided evolved from a "nice-to-have" to a "must-have." The market caught up to what our early customers already knew.

If I've learned anything from building and selling a $25M company, it's this: positive signals from customers are pure gold. You can lack industry support, struggle with funding, or even face personal challenges—but if customers are willing to pay for what you're building and stick with you through the rough patches, you have something worth fighting for.

One could argue that customer validation isn't just one of the four pillars—it's the foundation upon which everything else stands. Without it, the other pillars may eventually crumble, no matter how strong they initially appear.

4. Supportive Family and Friends Are Your Lifeline

Never underestimate the power of personal support when you're building something from nothing:

• A partner who believes in your vision

• Friends who listen to your struggles without judgement

• Family members who defend your choices to skeptical relatives

• Children whose future you're fighting for

• Fellow entrepreneurs who understand the lonely reality

Building Boardroom Insiders taught me that entrepreneurship can be profoundly isolating. Even those closest to me sometimes couldn't hide their concern—or confusion—about my choices.

My own mother regularly reminisced about the "great job with benefits" I'd left in the '90s, her voice tinged with genuine worry about my financial security. At family gatherings, I'd get the tilted head and furrowed brow when trying to explain what I was building.

Some friends would listen politely to my latest business challenge, then immediately pivot to telling me about a "fantastic opportunity" at their company—their well-intentioned way of throwing me a lifeline they thought I desperately needed.

With this chorus of concerned voices, self-doubt wasn't just an occasional visitor—it was practically a roommate.

Through it all, my husband was my unwavering foundation. He picked up the slack at home when I was working nights and weekends. He listened to my fears without rushing to fix everything. And most importantly, he never once suggested I give up—even during the moments when I was ready to throw in the towel myself. In fact, during my darkest periods of doubt, he would remind me why I started this journey and why it mattered.

Without this emotional bedrock, I'm not certain I could have weathered the storms that came with building a company from scratch. When you're innovating, the market might not understand you yet. Industry experts might dismiss you. Funding might be scarce. But if you have loved ones who believe in you—not just in your business model—you have something invaluable to sustain you through the inevitable challenges.

The Two-Pillar Rule: Your Minimum Viability Test

Here's the framework I've developed for entrepreneurs who are wondering if they should keep going or throw in the towel: You need rock-solid support from at least two of these four groups to keep going, and one of them must be customers or you need to pivot. Non-negotiable.

Let's look at some scenarios:

Strong customer interest + supportive family = Keep going This is a powerful combination. If people are willing to pay for your solution and you have the personal support to weather years of experimentation and building, you've got a viable path forward.

Funding + industry support, but no customer interest = Pivot If you have financial backing and industry leaders believe in your vision, but customers aren't buying, you need to rethink your offering. The market is sending you a message.

Customers + industry support, but family resistance = Seek balance This is tricky. Business viability is strong, but personal sustainability is at risk. Can you find ways to address family concerns while continuing to build? For example, can you keep your day job until you reach financial sustainability at home? This is what I did.

Funding + family support, but no industry or customer validation = Hard reset needed This is a warning sign. You have the resources to continue, but neither the market nor the industry is responding. It's time for a significant pivot or to consider a different opportunity.

What makes this framework particularly useful is recognizing that support isn't static—it evolves over time:

• Early-stage companies often rely heavily on founder funding and family support

• As you gain traction, customer support becomes increasingly important

• Industry validation often follows customer validation

• External funding might come after you've established customer and industry support

This journey will typically take much longer than you think. How long are you willing to hold on?

At Boardroom Insiders, we started with primarily family support and a small amount of funding. As we gained customers, industry leaders began to take notice. Eventually, we had strong support across all four pillars—but it took years to build that foundation.

I cannot repeat this often enough:

It takes much, much longer than you think.

When to Reassess

This framework isn't a one-time evaluation. You should revisit it:

• When facing major business challenges

• After significant market changes

• During personal life transitions

• When considering a pivot or new direction

• At least annually as part of your strategic planning

You Can't Build a Company Alone

Perhaps the most important insight from this framework is that entrepreneurship is not a solo journey. Despite the myths of the lone genius founder, successful companies are built with support from multiple stakeholders.

If you're struggling in isolation, that itself is a red flag. Building a company requires a community of believers—people who support you financially, professionally, commercially, and personally.

When I look back at the success of Boardroom Insiders, I can clearly see how support from all four pillars contributed to our $25 million exit. We had customers who loved our product, industry leaders who championed our solution, investors who believed in our vision, and family members who supported us through ups and downs.

The Bottom Line: Evaluate Your Support Pillars

When things get tough and you're questioning whether to continue, don't just look at your bank account or your emotions. Take stock of your support system:

1. Who is financially backing your vision?

2. Which industry leaders are endorsing your approach?

3. Are customers willing to pay for your solution and do they renew and refer?

4. Do you have the personal support needed for this journey?

If you have strong backing from at least two of these groups (ideally including customers), you likely have a foundation worth building upon. If not, it may be time to pivot or reconsider your approach.

Remember: Building a company is hard, but it's impossible without support. Make sure you have the right people on your side.

What challenges are you facing in your entrepreneurial journey? Email me at sharon@sharonkgillenwater.com with your questions, and I might address them in a future issue or an office hours session (for paid subscribers only).

Q: Regarding advisor contracts: how do you set/negotiate the value of the advisor’s contribution and set/align expectations? The only frameworks I am familiar with are Slicing Pie and the Founder's Institute FAST agreement.

A: You have excellent timing! I just finished negotiating my first advisory contract as an exited founder with a Finnish company, and they used the Founder Institute's FAST agreement, so I can speak directly to how this framework works in practice.

The FAST (Founder Advisor Standard Template) was a great starting point for our negotiation. What I appreciated most was its structured approach to equity compensation based on:

1. Performance level (basic, standard, or expert)

2. Company stage (idea, startup, growth)

3. Specific service areas (business strategy, product development, fundraising, etc.)

The company provided me with the complete schedule of benchmarks from the FAST agreement, which created transparency around expectations and compensation. They also provided a customized “Scope of Advisor Services,” based on the intersection of what they need and where I excel. These services fell into three main buckets:

• General mentorship and guidance from a three-time, exited founder

• Introductions to 50 B2C customers—easy, since I fit the target audience profile

• A defined number of social media posts across multiple platforms about the company, its product and the founders’ entrepreneurial journey

I was super confident I could hit it out of the park on all three of these things.

However…they also made two asks that I did not feel comfortable committing to because they don’t align with my strengths. Specifically, they wanted:

• Introductions to venture capitalists, which is definitely not my jam

• Introductions to potential B2B customers. The problem? Their B2B audience and offer is not yet defined, so I was not comfortable committing to that piece.

Peers counseled me that if I signed on for everything they were asking, I should negotiate for .25% to .50% more equity. But I decided I would rather keep the equity level the same as what they had offered, but ditch the requests that made me uncomfortable.

So, I proposed removing the two commitments that weren't in my wheelhouse.

This led to my first insight: it's better to excel at fewer things than underperform across more responsibilities.

The equity percentage remained the same, but my responsibilities became more focused on areas where I knew I could truly add value. This approach created a win-win: they got a fully committed advisor in areas where I could make the biggest impact, and I avoided disappointing my new partners.

Here's what worked well in my advisor negotiation using the FAST framework:

1. Be honest about capabilities: By candidly sharing which responsibilities I could excel at versus those I might struggle with, we created more focused and realistic expectations.

2. Consider the company stage: The FAST agreement adjusts equity based on company maturity. Early-stage companies typically offer more equity to compensate for higher risk.

3. Seek peer input: Before finalizing, I consulted with other founders who had served as advisors. Their insights helped me understand market norms and potential pitfalls.

4. Look beyond equity: While equity is important, also consider whether the company's mission, team, and product excite you. I found myself more willing to be flexible on terms because I genuinely believe in what they were building (more on that later - announcement coming soon!)

Ask Me Anything: Got a burning question about building or scaling your business? Drop me a line at sharon@sharonkgillenwater.com. I personally read every email and respond to as many as possible. The most interesting questions might be featured in future issues (with your permission, of course). No question is too basic or too complex—I'm here to help you succeed!

Come to My Office Hours: Did you know that paid subscribers have access to office hours with me and other founders? Our next session is Wednesday, May 21st from 10-11am PT. Is $10/month worth chatting with me and a bunch of other founders a few times a month? You bet it is, so maybe you should upgrade here. Would love to see you and hear about what you are working on!

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