In Jotform’s early days, the entire customer support team consisted of just one very busy, tired and overworked person: me.

One evening as I was preparing to leave, I got a support ticket from a small ecommerce founder in Canada whose online form wasn’t behaving the way it should. Her payment form wasn’t connecting to the payment processor, and every attempt ended in an error message that made no sense.

I understood her frustration. As a founder myself, I was acutely aware of the pain of trying to run a business and feeling like nothing was going your way. When I dug into her form, I found the problem a few minutes later: a mismatch between test mode and live credentials. It wasn’t her mistake — the toggle between the two modes was buried deep in the settings, and even I, the person who literally built the product, almost missed it.

That support ticket successfully solved one customer’s problem. But far more importantly, it forced me to redesign that part of the product that wasn’t cutting it with users.

As my business began to scale, I eventually hired full-time customer support staff to handle the many inquiries we were being flooded with daily. Was I relieved not to be fielding these requests all day, every day? Yes. But I also wouldn’t trade that experience for the world. Here’s why.

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You learn who your users are — and what they value

When you’re running a business, it’s hard to overstate the importance of having your ear to the ground. In the same way that politicians are always trying to take the pulse of the common man and woman, leaders have to have a handle on how customers are actually using their products.

Even nearly 20 years after launching Jotform, I still spend at least an hour each day sifting through our support forum. I get so much data from these forums — what are the common complaints? What features would be helpful? Because I make it a point to stay on top of what our users are saying, patterns become evident that I wouldn’t otherwise know about.

It’s easy to assume you understand your users when you’re building a product. After all, you’re solving a problem you care about — maybe even one you’ve personally experienced. But building for yourself is very different from building for thousands (or millions) of people. When you’re not interacting with users regularly, it’s easy to project your own preferences onto them.

During those early years answering support emails myself, I realized that people don’t actually care about impressive-sounding integrations or tech-heavy features. They care about outcomes, plain and simple. Doing support helps you continue seeing your product through their eyes — as a tool that either simplifies their life, or doesn’t.

You build trust

Back in 2006, it was clear there was a market for a drag-and-drop form builder, and I wasn’t the only one who noticed. Several other formidable competitors — including Google — entered the form-building arena around the same time I did. It would have been very easy for me, a bootstrapper with no outside funding, to have been wiped clean off the map before I even released my first MVP.

That didn’t happen. One reason for our continued survival was because it was very obvious to my users that I took my business seriously. When I talked with customers about their issues, I really listened. I took feedback to heart and worked tirelessly to make my product better. That sort of commitment didn’t go unrecognized, and Jotform quickly developed a reputation for having excellent, personalized customer service.

Word-of-mouth referrals are worth so much more than a pricey ad spend, and a significant portion of our business in those nascent days came to us in exactly that way. When users know they can count on you to answer their questions and fix their problems, they stick around. They also tell other people.

It keeps your ego in check

Don’t get me wrong — it’s not always easy to hear honest feedback. As anyone who has spent time online knows, people can be blunt, if not downright mean. It’s hard not to take criticism personally, and even harder not to get defensive.

This is part of why I continue to spend time in our support forums, even as I’ve transitioned from a founder to a CEO and our user count has grown to 24 million: It keeps me grounded. Support conversations are honest — really honest. Users don’t sugarcoat things. They tell you exactly what’s broken, why they’re frustrated and what they wish your product could do. When you willingly step into that feedback loop, you’re getting the unfiltered real deal. It can hurt, but it also forces you to make better decisions based on lived user experience.

Spending time in customer support made Jotform better. It also made me better at my job. I’m incredibly glad I was able to hire a support team to handle all those tickets, but no founder should ever fully leave the trenches behind.

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In Jotform’s early days, the entire customer support team consisted of just one very busy, tired and overworked person: me.

One evening as I was preparing to leave, I got a support ticket from a small ecommerce founder in Canada whose online form wasn’t behaving the way it should. Her payment form wasn’t connecting to the payment processor, and every attempt ended in an error message that made no sense.

There’s a kind of arbitrage in innovation that’s easy to miss because it doesn’t look like arbitrage at all. It lives in the gap between what physics allows and what institutions assume is possible. The reason it persists is that exploiting it requires developing genuine expertise in domains where most have neither the background nor the patience.

In 2019, I invested in SpaceX. What caught my attention wasn’t the headline features like reusable rockets or lower launch costs. It was watching them systematically demolish constraints that the entire aerospace industry treated as fundamental.

At the time, many investors, including me, were busy arguing about software multiples and growth loops. SpaceX was doing something much rarer: showing that a large fraction of what we call “impossible” is really just a coordination problem that no one had been sufficiently motivated to solve.

That investment was a turning point. For several years, I’d been a generalist investor, moving where the heat was. Consumer, enterprise, and a little hard tech when it came with enough narrative support. I wasn’t bad at it. But I wasn’t learning much either.

SpaceX clarified something I’d felt but hadn’t yet put into words. The biggest breakthroughs don’t come from optimizing within known constraints. They come from noticing that some constraints aren’t real. They’re habits, incentives, or historical accidents. And they require the technical grounding and nerve to see what happens when you ignore them.

The linearization fallacy

The Vannevar Bush–era model of innovation assumes a pipeline: basic research generates knowledge, applied research converts knowledge into prototypes, and development converts prototypes into products. This maps cleanly to how we organize universities, corporate R&D labs and government funding. It also happens to be backwards.

If you trace the causal history of transformative technologies — think transistors, lasers, the internet, GPS, mRNA vaccines — almost none emerged from linear knowledge transfer. They came from programs that collapsed the artificial boundary between “understanding nature” and “solving problems.”

This pattern appears often enough that it’s hard to dismiss as a coincidence. Donald Stokes formalized it in his analysis of scientific research by identifying Pasteur’s Quadrant: work that pursues fundamental understanding through the lens of immediate practical constraints.

Pasteur didn’t first understand microbiology and then apply it to fermentation. Investigating fermentation was how microbiology itself was built.

I first encountered Pasteur’s Quadrant in 2022, after starting Interface Fund and narrowing my thesis to biology, hardware, and infrastructure. We overlapped heavily with DARPA, were among the first VC checks into DARPA-funded companies, and became familiar with how they innovate and operate.

This isn’t a semantic distinction. It’s a claim about the structure of possibility space. There are regions of that space, high-value regions, that are only accessible when you optimize simultaneously for scientific novelty and practical application. If you decouple these objectives, even slightly, you end up searching a different region altogether.

DARPA’s hit rate makes sense once you see this. Packet switching, satellite navigation, RISC architectures, speech recognition, autonomous systems: these didn’t come from applying existing science to new problems. They came from organizations that refused to separate the question “what’s true?” from “what’s useful?”

SpaceX’s reusability breakthrough has the same structure. You don’t get there by first solving atmospheric reentry physics and then engineering an application. You get there by treating the coupled problem — entry physics, thermal materials, landing dynamics, propellant margins and economics— as a single integrated optimization. Progress in any subdomain opens new possibilities in the others.

Where breakthroughs actually come from

The key insight is simple. The objective function you optimize determines which regions of possibility space you can even perceive. Change the objective, and previously invisible solutions become obvious. This is why most breakthroughs seem obvious in retrospect. They were always there; you just needed the right lens to see them.

Operating in Pasteur’s Quadrant isn’t just intellectually different — it’s operationally different. It requires founders who can hold deep technical expertise while maintaining the flexibility to restructure problems from first principles. It requires organizations that can sustain exploration even as they scale, rather than collapsing into pure optimization.

And it requires a particular relationship with time: comfort working on problems where the compounding insight happens over years, not quarters, and where most of the value emerges in the final phases after long periods that look unproductive from the outside.

The companies that will matter over the next decade are those that systematically exploit this gap. They do it by operating in Pasteur’s Quadrant, coupling fundamental scientific questions with immediate practical constraints in ways that reveal new possibility space.

The framework exists, and we’re learning how to execute on it. Capital is beginning to follow. And there’s a specific kind of founder who is well positioned to benefit: someone with deep technical expertise, who has noticed that something everyone treats as a constraint is actually just a convention, and who is temperamentally incapable of letting that observation go.

There’s a kind of arbitrage in innovation that’s easy to miss because it doesn’t look like arbitrage at all. It lives in the gap between what physics allows and what institutions assume is possible. The reason it persists is that exploiting it requires developing genuine expertise in domains where most have neither the background nor the patience.

In 2019, I invested in SpaceX. What caught my attention wasn’t the headline features like reusable rockets or lower launch costs. It was watching them systematically demolish constraints that the entire aerospace industry treated as fundamental.

For many freelancers and solopreneurs, there comes a point where the workload feels full, the opportunities are growing and the question starts to surface: Should I scale?

The freelancing world often presents scaling as the “natural” next step — turn yourself into an agency, build a team and watch the income multiply. But the reality is far more nuanced. Scaling is optional. It’s not a rite of passage. And it’s certainly not the only way to grow a business.

For some, the best next step isn’t launching a full agency. It’s something smaller, more flexible and more aligned with the way they actually like to work: a micro-agency.

What a micro-agency actually is

A micro-agency is essentially a small, agile extension of your freelance business. Instead of building a large team, you maintain a lean bench of 1-3 trusted subcontractors you tap when you need overflow help or specialized expertise.

It allows you to:

• take on bigger or more complex projects,
• increase the value and volume of your services,
• maintain control over client relationships,
• and avoid the pressure of managing a full agency operation.

In many cases, clients never interact directly with your subcontractors. You remain the face of the work — and the one managing quality, communication and strategy.

This model captures the best of both worlds: the earning potential of an agency and the personal touch of a freelancer.

Why scaling is optional (and why that matters)

One of the biggest misconceptions in the freelance world is that growth must involve hiring. Some freelancers assume that once they hit capacity, the only “real” path forward is becoming a traditional agency.

But scaling is not mandatory. It’s a choice.

You shouldn’t scale because you feel pressured to, or because others in your niche are doing it. You scale because you see opportunities you want to capture — and because saying no to high-value projects is starting to feel like a loss rather than a relief.

If you’re not excited by the idea of managing people or stepping away from the hands-on work you love, you’re not required to. A micro-agency is simply one option for refining your business purpose.

How to know it’s the right time

Most freelancers consider scaling in two common situations.

First, they’re simply too busy. Their calendar is full, their inbox is overflowing, and they’re turning down work they’d genuinely like to accept. In this situation, adding a subcontractor can allow for breathing room and increased revenue.

Second, they’re starting to attract projects that exceed their personal bandwidth or skill set. For example, a copywriter who consistently gets asked for SEO audits, email automations or graphic design may bring in specialists to expand their offering without expanding their job description.

But there are “false signals,” too — the red flags that make freelancers feel like they should scale even when it’s not the right move. Feeling bored, comparing yourself to peers or thinking your income has plateaued are not reasons to hire. Hiring won’t fix a weak pipeline, unclear services or inconsistent marketing. Those are problems to address internally before growing the team.

The benefits of a micro-agency model

In my own business, running a micro-agency has allowed me to capture larger, more lucrative projects that would otherwise go to traditional agencies. Because I work with a small roster of carefully chosen subcontractors, I can scale up or down as needed — without promising a certain volume of work or adding the overhead of employees.

This flexibility is key. It gives you the ability to:

Many clients appreciate this model because they want the attention and responsiveness of working with one person — not a large, impersonal agency — while still accessing a well-rounded skill set. When you manage the client relationship directly, and subcontractors operate behind the scenes, clients get the best of both worlds.

Start small: Delegation without the overwhelm

If you’ve never delegated before, the idea of handing off client work can feel intimidating. So don’t start there.

The best entry point is often outsourcing simple administrative tasks to a virtual assistant. This builds foundational delegation skills: writing instructions, giving feedback, setting expectations and creating basic systems. It gives you a safe place to practice “being the manager” before you begin delegating deliverables.

Once you’re comfortable, the next step is outsourcing overflow work within your own service line. This is easier because you already understand the process, quality standards and client expectations. You know what good work looks like, which means you can evaluate subcontractors more confidently.

I always run a small test project first. It gives me a clear picture of how someone communicates, how they receive feedback and what they actually enjoy doing. I also ask subcontractors directly what kinds of projects they prefer and what they’d rather avoid. It’s a small step that prevents major mismatches later.

How to manage subcontractors without becoming a “manager”

A major fear freelancers have is that scaling automatically turns them into full-time managers. But with a micro-agency, you remain the primary doer. You simply add structured collaboration to your toolkit.

The key is setting clear expectations from the start, including what the deliverables are, when they’re due, how revisions work and how communication will happen.

You don’t need weekly team meetings. You don’t need complicated software. You need clarity. And you need subcontractors who value transparency as much as you do.

At this stage, you also decide what you won’t outsource. You might choose to keep client strategy, discovery calls, high-level writing or editing as your domain. A micro-agency is not about removing yourself from your business — it’s about amplifying your capacity without diluting your impact.

Scaling in a way that fits your personality

Some freelancers love leading teams, signing clients, and overseeing operations. They’re natural agency builders. Others enjoy client work and want to stay closely involved. A micro-agency lets them remain in the craft while still increasing earnings.

The best version of scaling is the one that aligns with who you are, not who you think you’re supposed to be. If you thrive in collaboration but don’t want a full team, a micro-agency works beautifully. If you love sales but dislike doing the work, a traditional agency may be the right fit. And if you love being a true solo operator, that path is equally valid.

What matters is building a business that lets you grow without losing the parts of freelancing that made you choose this career in the first place.

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For many freelancers and solopreneurs, there comes a point where the workload feels full, the opportunities are growing and the question starts to surface: Should I scale?

The freelancing world often presents scaling as the “natural” next step — turn yourself into an agency, build a team and watch the income multiply. But the reality is far more nuanced. Scaling is optional. It’s not a rite of passage. And it’s certainly not the only way to grow a business.

Entrepreneurs are decisive by nature. But one critical decision that often gets deferred or approached too casually is the selection of a financial advisor. Many founders and business leaders wait until a major liquidity event or tax issue forces the conversation. That’s a missed opportunity.

Choosing the right advisor early can help preserve wealth, create flexibility and align your business and personal financial strategies well before the pressure is on.

Financial advisors, lawyers, accountants and investment bankers aren’t all built the same. Some are excellent at portfolio construction but fall short when it comes to complex planning or business integration. Others are tied to institutions that limit their objectivity. The right fit depends on where you are in your business lifecycle and what kind of support you actually need.

Here’s what to consider.

Understand your own complexity

Entrepreneurs and executives operate in a more complex financial environment than most individuals. Your assets may be illiquid, your income irregular and your tax exposure dynamic. If you’re still growing a business, your advisor should be able to engage in terms not just of investment returns, but also in terms of cash-flow strategy, entity structure, exit planning and succession.

If you’re a public company executive, issues like stock option planning, RSUs, trading windows and corporate governance rules all shape how you can access and manage wealth. The financial advisor should be fluent in these dynamics and have experience working with clients whose wealth is tied to business outcomes, not just market moves.

Insist on fiduciary alignment and transparency

The term “fiduciary” is worth clarifying. A fiduciary advisor is legally obliged to put your interests ahead of their own. This isn’t just a best practice; it’s a structural safeguard.

Advisors held to a fiduciary standard — typically those affiliated with Registered Investment Advisor (RIA) firms — are more likely to offer objective recommendations, transparent pricing and clear disclosure of potential conflicts.

In contrast, advisors tied to banks or brokerage firms may operate under the lower standard of “suitability,” and could be incentivized to recommend proprietary products.

With these distinctions in mind, ask any potential advisor the following:

• Will you act as a fiduciary at all times?

• Will you sign a fiduciary agreement?

• How are you compensated, and do you (or does the firm you work for) receive any revenue as a result of managing my account other than from me?

These questions help clarify whether your advisor’s business model supports independent thinking, which is good for you — or product distribution, which isn’t.

Evaluate how services are structured

An important but often overlooked element in advisor selection is how advice is delivered and supported behind the scenes. An up-to-date, conflict-conscious structure separates three key functions.

1. Advice: The person or team providing guidance.

2. Custody: The institution holding your assets securely.

3. Product access: The universe of investments available to you.

When these roles are housed in separate entities, your advisor is more likely to act in your interest rather than follow incentives tied to proprietary products or institutional relationships. If you ever want to change one piece — say, your custodian — you won’t have to disrupt your entire advisory relationship. This model gives you more control, flexibility and transparency.

Don’t overlook technology and integration

The advisor’s platform should include more than spreadsheets and statements. Look for firms that use planning technology to model scenarios in real time, track tax exposures and integrate with your legal and accounting partners. Secure communication and document-sharing tools should be standard, not aspirational.

Ask about the full scope of service

Wealth management for entrepreneurs is about more than investments. It should include tax-aware planning, business continuity strategies, estate and philanthropic guidance and a structured client service process.

Ask how frequently meetings occur, whether the advisor works with other professionals in your network and how the firm manages feedback and performance reviews.

The real value of an advisor often lies in what happens outside of portfolio returns: anticipating challenges, planning across generations and keeping your goals central as your business evolves or exits.

What else to ask before you commit

Even the strongest referral warrants due diligence. Once you’ve established that an advisor operates under a fiduciary standard and offers the structural independence you expect, dig into how they actually serve clients. Ask:

• What types of clients do you typically work with, and how do their needs compare to mine?

• How do you define success in your client relationships, and how is progress measured over time?

• What does your onboarding process look like, and who will I interact with day to day?

• How do you stay current with issues affecting business owners and executives?

• Can you walk me through a real (anonymized) example of how you helped a client solve a complex problem?

• Can I speak to a few current clients with similar profiles?

If the advisor hesitates, deflects or offers generic answers to these questions, consider it a red flag. Transparency, specificity and situational relevance should be standard, especially at this level of engagement.

Putting it together

There’s a tendency to treat financial advisors like product providers, but for entrepreneurs, the relationship should feel more like a strategic partnership. You require someone who understands how your business success translates into personal wealth, who can spot issues before they become problems and who has the independence and infrastructure to act in your best interest.

A thoughtfully selected advisor brings structure, insight and accountability to decisions that carry high stakes. The earlier you establish that partnership, the more effectively you can make plans on your own terms.

Entrepreneurs are decisive by nature. But one critical decision that often gets deferred or approached too casually is the selection of a financial advisor. Many founders and business leaders wait until a major liquidity event or tax issue forces the conversation. That’s a missed opportunity.

Choosing the right advisor early can help preserve wealth, create flexibility and align your business and personal financial strategies well before the pressure is on.

When people encounter something new, their brains start making sense of it immediately. Visual signals are read first, shaping impressions before words have a chance to catch up. We instinctively decide whether something feels clear and reliable well before we think about what it’s actually saying.

When someone lands on a website or opens a product interface, their brain is not asking, What is this company saying? It is asking, Does this make sense? Does this feel stable? Can I tell what to do next?

Design resolves these questions through structure. Hierarchy directs the user’s attention. Spacing establishes relationships of information. Consistency signals reliability over time. When those signals conflict, cognitive friction happens, even if the user cannot name the source of discomfort. Alongside structure, tone and visual character shape how that system feels, whether it comes across as confident, restrained, approachable or distant.

This is why we look at the design systems like language. Design communicates meaning through organization and pattern, shaping understanding before explanation enters the picture.

Design reduces cognitive load before it builds persuasion

In many business contexts, persuasion is treated as the end goal. But people need to understand something before they can be convinced by it. Our capacity to process information is limited, and when an interface, website or brand system asks for too much effort up front, most people simply disengage — not because they disagree, but because it feels harder than it needs to be.

Good design lightens the mental load without calling attention to itself. Information feels easier to follow. Screens don’t ask users to stop and interpret what’s in front of them. The next step is clear enough that people keep moving.

Teams that incorporate this logic into their work tend to see stronger conversion, retention and adoption over time — not because the experience is persuasive, but because it removes friction. When people don’t have to spend energy figuring out how something works, they’re more willing to engage, commit and move forward. Design rarely persuades on its own. Its real value is making understanding feel effortless.

UI reflects organizational thinking

User interfaces are often discussed as surface layers. In reality, they are structural and inseparable from user experiences. That is why our work is often guided by both disciplines, UI and UX. Every interface represents hundreds of decisions: what to prioritize, what to defer, what to hide and what to explain. Those decisions reveal how an organization thinks about its users, its product and what it chooses to prioritize.

When UI feels uneven, it is rarely a surface-level design issue that is sticking out. It is often the visible outcome of internal misalignment. Competing priorities. Unclear ownership. Decisions made in isolation. Interfaces that feel calm and intentional usually emerge from organizations with internal clarity. Design language, in this sense, becomes a proxy for organizational pulse. UI is not just what users see. It is what internal decisions look like when exposed.

Websites as memory systems

From a psychological perspective, brands live in memory, not messaging. Memory is associative. People remember patterns more readily than taglines. They remember how something felt to use long after specific claims fade. Websites function as external memory systems for businesses. Recognition builds through repeated patterns, consistent structure and a rhythm people come to expect across pages. When those elements shift erratically and when they are not in sync, memory weakens.

This is why change needs a point of view. When updates focus only on what’s visible, there’s nothing for recognition to build on. Each shift feels new, but not familiar. Strong brands evolve over time by holding onto what gives them shape, even as their visual expression adapts. That continuity is what allows memory to accumulate.

Design language accelerates decision-making inside organizations

Design language is often justified externally, for customers. But its internal impact is just as significant. When teams share a common visual and interaction system, decision-making improves and speeds up. Fewer discussions revolve around personal taste. More attention is directed toward intent and outcome.

This aligns with research on shared mental models. Teams perform better when they hold aligned representations of how systems work. Design language makes those representations tangible. Instead of abstract guidance, it provides concrete reference points. Instead of opinion-driven feedback, it introduces a framework. In complex organizations, this may be one of the most practical forms of alignment available.

The risk of treating design as expression instead of structure

When design is seen mostly as expression, it starts to follow taste and trends, which often leads to starting over again and again. When treated as a structure, it gains durability, and the design is more timeless. Structure does not mean rigidity. It means logic. It means understanding which elements must remain stable and which can evolve without breaking meaning.

Without a clear distinction, design fatigue can set in. Things stop feeling connected. Interfaces lose their rhythm. Over time, what the brand claims and what people experience begin to drift apart. The change is gradual, but it adds up.

A view on design as investment

Design is often judged by what changes on the surface, such as new visuals, updated pages or cleaner interfaces. But its real value shows up in what people don’t notice. Fewer moments of confusion. Less second-guessing. Fewer stops where progress should feel continuous. From a business standpoint, this prevention has a measurable impact. Lower number of support tickets. Higher completion or signup rates. And overall reduced friction across touchpoints. Design does not add meaning. It preserves it.

Every organization has a design language. When it no longer reflects how the business actually works, it needs to be brought back into alignment. Misalignment forces people to stop, interpret and second-guess. In a world where time and patience are limited, companies that endure are the ones that remove that extra work.

Design is how that understanding takes shape.

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When people encounter something new, their brains start making sense of it immediately. Visual signals are read first, shaping impressions before words have a chance to catch up. We instinctively decide whether something feels clear and reliable well before we think about what it’s actually saying.

When someone lands on a website or opens a product interface, their brain is not asking, What is this company saying? It is asking, Does this make sense? Does this feel stable? Can I tell what to do next?