From Wall Street to 2x Exited Founders: How these Siblings Built and Sold the Same Startup Twice  |  Ziyaad Ahmed

What do you do when your startup gets shut down right after a successful exit?

If you're Ziyaad and Anuscha Ahmed, you buy it back and sell it again.

Ziyaad Ahmed's journey from a data-driven Wall Street analyst at Citadel to a two-time startup founder is a masterclass in applying an investor's mindset to entrepreneurship. Together with his sister and co-founder, Anuscha, he has one of the most unusual founder stories you'll ever hear.

After pioneering the Buy Now Pay Later (BNPL) industry in the Middle East, they built Spotii from bootstrap to a life-changing acquisition by Australian fintech Zip in just 18 months—delivering a 5x return to their early investors. But when Zip made a strategic pivot and decided to shut down their Middle East operations, Ziyaad faced what he calls a "near-death experience."

Instead of walking away, the siblings negotiated to reacquire their own technology and brand name, pivoted from B2C to a B2B white-label model, and sold the company again to NymCard just three months later. Today, Spotii's technology powers lending solutions across banks in Saudi Arabia, has a monopoly on Buy Now Pay Later in Qatar, and serves both banks and fintechs throughout Dubai.

Drawing from his finance background at Wharton and Citadel, Ziyaad provides a founder's playbook for fundraising and exits. He breaks down the three factors early-stage investors actually care about (spoiler: traction ranks third), shares his enterprise sales methodology that landed clients like Amazon and Shein, and explains why he's betting his next company, Quanooni, on AI as the next "tectonic shift" in technology.

This is a deep dive into resilience, sibling partnerships, and what it really takes to build and exit—twice.

Guest Background

Ziyaad Ahmed is a serial entrepreneur and co-founder of Quanooni, an AI platform for legal professionals that recently closed a $2M pre-seed round. Previously, he co-founded Spotii, one of the first Buy Now Pay Later platforms in the Middle East, which achieved two successful exits.

Before entrepreneurship, Ziyaad was a long/short equity analyst at Citadel, focusing on retail and consumer tech with big data applications. He holds degrees from Wharton (University of Pennsylvania) and UC Berkeley (Data Science), and previously worked at Afterpay in Silicon Valley. He comes from a family of entrepreneurs in Pakistan and moved to Dubai in 2020 to build Spotii with his sister.

Agenda:

The Wall Street to Startup Transition

• How his analytical background at Citadel and experience with big data applications shaped his approach to building startups

• The decision to leave a successful Wall Street career to pioneer BNPL in an untested Middle Eastern market

• Why he went back to UC Berkeley to learn data science and coding to bridge the gap between financial analysis and technology

The Sibling Co-Founder Dynamic

• Why he describes the co-founder relationship as "very much like a marriage" and the unique advantages of working with family

• How their parallel Wall Street careers and shared Wharton education created a foundation of trust and common business language

• The challenges of transitioning from siblings to business partners and maintaining both relationships

The Spotii Double Exit Story

• The Thesis: Why they identified BNPL as perfect for the Middle East (Sharia-compliant, interest-free, growing e-commerce)

• Bootstrap to Exit: Building from personal savings to acquisition by Zip in 18 months with 1 million users and 1,500+ merchants

• The Strategic Acquisition: How Zip's vision of a global BNPL platform aligned with their regional success

• The "Near-Death Experience": When Zip decided to focus on core markets and shut down Middle East operations

• The Reacquisition: Negotiating to buy back their technology and pivot to B2B white-label solutions

• The Second Exit: Selling to NymCard just three months later and the continued success of their technology across the region

The Investor's Playbook for Founders

• The Three-Factor Framework: Team (most important), Market Size, then Traction—and why this order matters for early-stage fundraising

• Thinking Like an Investor: How their finance backgrounds helped them understand what investors want and structure deals accordingly

• Bootstrap vs. Raise: Why he recommends bootstrapping early validation before seeking external funding

Enterprise Sales Mastery

• The #1 Rule: Always control the sales process and never accept "we'll discuss internally and get back to you"

• Building Consensus: How to help your champion build internal support within large organizations

• Major Client Wins: Landing partnerships with Amazon, Shein, and other major retailers

The AI Bet: Building Quanooni

• Why he believes AI represents the third major technological shift of his lifetime (after internet and mobile)

• How early experience with GPT in Spotii's risk engine convinced him to build an AI-native company

• The approach to legal tech: making professional tools as simple as "downloading an app on your phone"

  Key Takeaways & Frameworks

  For Founders Raising Capital:

  1. Team First: Early-stage investors are primarily backing you, not your current metrics

  2. Market Size Second: Prove the problem is large enough to matter (existing or potential market)

  3. Traction Third: If you nail the first two, investors give you benefit of the doubt on early numbers

  For Enterprise Sales:

  • Never lose control of the sales process

  • When someone says "we'll discuss internally," immediately schedule a follow-up and provide next-step materials

  • Focus on helping your champion build internal consensus

  The Entrepreneur Mindset:

  • "It's not intelligence or technical capability—it's grit and resilience. That's the number one thing."

  • Good process probabilistically leads to good outcomes

  • Competition keeps you sharp and validates your market thesis
    
    

Memorable Quotes

On entrepreneurship: "It's not the intelligence, it's not even necessarily the technical capability. I would say it's grit and resilience. That's the number one thing."

On co-founders: "You have to fully understand that this is a person that you're getting into a very intimate relationship with. It is very much like a marriage."

On enterprise sales: "My number one secret for enterprise sales is that I will always control the sales process. I never let it get out of my control."

On the founder journey: "The lows are really low. That's just reality."

On building with family: "It's wonderful to be able to have somebody who basically I know that if I'm not in the room or she knows that she's not in the room, we always have each other's backs."


Companies & Resources Mentioned

• Current: Quanooni (AI platform for legal professionals)

• Previous: Spotii (acquired by Zip, then reacquired, then acquired by NymCard)

• Education: Wharton School (University of Pennsylvania), UC Berkeley

• Previous Roles: Citadel (hedge fund), Afterpay

• Major Clients: Amazon, Shein, various banks across MENA region

• Community:Opus (founder community)