How to Actually Scale a Startup (From a Founder Who Did It 3x)

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Waseem Daher co-founded Pilot in 2017, but the idea had been taking shape long before that.

While studying computer science and electrical engineering at MIT, he built strong technical foundations and met the co-founders he would go on to start three companies with.

But in his early startup experiences, Waseem ran into a recurring problem. Managing finances, bookkeeping, and taxes was always a painful distraction from building the actual business.

After two successful exits, first with Ksplice, which was acquired by Oracle, and then with Zulip, which was acquired by Dropbox, he realized that this pain point wasn’t just his. It was universal among founders.

So they built Pilot. Not another SaaS tool, but a full-stack finance firm designed to feel like an extension of your startup.

Waseem had lived the problem. Now, he was solving it, building a company that lets founders focus on growing their business while Pilot handles the rest.

Listen to Waseem’s interview on YouTube, Spotify, or Apple Podcasts.

Thank you to our sponsor:

• Rho - A business banking platform, purpose-built for startups.

Let’s dive in.

Rho is a business banking platform, purpose-built for startups and they work with everyone from two-person YC startups with world-changing ideas to publicly-traded enterprises.

With Rho, founders get:

• A single pane of glass they can use to run and scale their business from Day 1: Bank account, corporate cards to start running – and expense management, bill pay automation, and accounting to help you move fast as you scale.

• The big thing with Rho: Every customer has a "person" at Rho. 24/7 customer support - phone, text, email - they will be there at every critical milestone in your startup's journey.

To learn why startups choose Rho, visit www.rho.co today.

• The Hard Part Is Scaling, Not Starting. Early traction can feel validating, but Waseem emphasizes that the real challenge begins once the business is running and growing. Founders often obsess over launching, but sustaining operational excellence, service quality, and culture at scale is a completely different beast. Success means thinking far beyond the MVP.

• Solve a Pain You Deeply Understand. Pilot was born from a pain Waseem personally experienced. This founder-market fit gave the team clear insight into customer needs and a compelling starting point. If you're solving your own problem, you likely have an intuitive understanding of what "excellent" looks like.

• The Best Ideas Often Seem Boring. Great startups don’t always come from flashy ideas. Pilot succeeded by rethinking such a painful, overlooked part of running a business as accounting, and building a full-stack solution. Waseem highlights how "unsexy" problems can offer massive markets, especially if they’ve long been underserved.

• You Only Need One Yes. Even with a strong founding team and a good track record, Waseem emphasizes that every funding round almost didn’t happen. Rejection is common, and your job isn’t to convince everyone; you just need one investor who believes. Don’t be discouraged by no’s; keep going until you find your yes.

• Fundraising is a Means, Not the Mission. Fundraising is a “necessary evil,” not the goal of your company. Success isn't defined by which firms back you but by whether you're solving a real problem customers want to pay for. Don’t let investor interest (or lack thereof) become a proxy for validation.

• Pick Investors Like Long-Term Partners. The Series A investor will be in your life for years, possibly texting you weekly. Choose based on chemistry and alignment, not just valuation. Pilot used their seed round partly to "audition" future Series A investors by giving small checks to people they wanted to test working relationships with.

• Founder-Led Sales Is Non-Negotiable Early On. Waseem personally sold Pilot’s first 100+ customers and stayed deep in the process. Why? Because it’s your fastest feedback loop on what’s working. If you don’t understand objections firsthand, you can’t fix them. Founders often try to delegate sales too early, but you shouldn’t.

• Start Niche, Then Expand. Even though Pilot could theoretically serve every business, they started with startup founders. Going niche early makes everything easier: messaging, targeting, referrals, and building domain knowledge. It’s better to be beloved by a focused group than vaguely liked by a large one.

• Marketing Attribution Is Messy. Trust Customer Intimacy. While attribution models (first-touch, last-touch) are tempting, Waseem points out that they’re often misleading. He argues that real conviction in marketing bets comes from knowing your customers deeply, not spreadsheets. Founders should spend time talking to users and experiencing their world firsthand. That’s how you identify campaigns that resonate, even if ROI isn’t obvious upfront.

• Founders Must Reevaluate Their Role as the Company Grows. As Pilot scaled, Waseem stepped away from the CEO role to return to work he finds energizing. The lesson: your ideal role evolves over time, and it’s okay to shift. Founders often move from “building the thing” to “building the machine that builds the thing,” but that path isn’t always energizing. Founders should regularly ask: Does this role align with my strengths, my energy, and the company’s needs? If not, changes are worth exploring.

Listen to Waseem’s interview on YouTube, Spotify, or Apple Podcasts.

00:00 What’s coming in the episode…

00:27 Introduction

01:36 Waseem’s passion for startups

03:58 Starting Pilot

05:43 Why was it the right time to start Pilot

13:30 Early days at Pilot

19:27 Raising capital for Pilot

22:32 Waseem’s mentality on fundraising

26:36 The story behind Pilot’s Series A round

30:22 Pilot’s first sales

34:09 Pilot’s ICP

36:44 Growth strategies back then

40:09 Growth strategies today

48:34 The evolution of Waseem’s role as a founder

54:25 Be a part of Pilot

Best,
Justin

Founder of Just Go Grind

P.S. Hiring? Check out the team at Athyna