Voice of Innovation: How David Daneshgar Transformed Poker Strategy into AI Business Success
David Daneshgar shares how he applied poker strategy to build Whippy AI, the communication platform that's transforming how you engage with customers through intelligent voice,SMS, and email AI agents
David Daneshgar, co-founder of Whippy AI, has charted an extraordinary path from World Series of Poker champion to tech innovator. After ranking among the world's top tournament players and winning a WSOP bracelet in 2008, Daneshgar leveraged his analytical mindset to pursue an MBA at the University of Chicago Booth School of Business. This led to co-founding BloomNation, a venture-backed startup that has generated over $1 billion in revenue for florists, before launching Whippy AI in 2021—a company revolutionizing business communication through AI-driven voice, SMS, and email automation.
In an exclusive interview with AI World Today, Daneshgar reveals how the strategic thinking honed at poker tables directly translates to business success. From managing imperfect information to making calculated bets with limited resources, his poker background has proven invaluable in building a platform now handling tens of millions of conversations monthly across multiple channels.
Welcome to AI World Today, David. You've had quite a remarkable journey from World Series of Poker champion to co-founding multiple successful companies. Could you introduce yourself to our audience and share what motivated your transition from professional poker to entrepreneurship?
My journey into poker began while I was attending UC Berkeley in 2003, where I taught a course called The Probability and Statistics of Gaming. Shortly after, the poker boom hit, and I was able to apply my analytical skills to competitive play. This led to an incredible run, which included ranking as one of the top five tournament players in the world in 2006 and winning a World Series of Poker bracelet in 2008. While poker was a high-stakes, high-reward game, I wanted to apply those same principles to something even bigger—business and tech startups. A friend and mentor of mine, Jerry Buss, the late owner of the Lakers, wrote my letter of recommendation to business school, and I decided to pursue an MBA at the University of Chicago Booth School of Business. That’s where I co-founded BloomNation, a venture-backed startup that has generated over $1 billion in revenue for florists.
In 2021, I launched Whippy AI, a company focused on revolutionizing business communication with AI-driven voice, SMS, and email automation.
Your journey from poker champion to tech CEO is fascinating. How have the strategic thinking and risk assessment skills from your poker career influenced your approach to entrepreneurship and building Whippy AI?
Poker and entrepreneurship are deeply connected. In poker, you’re constantly making decisions with imperfect information, assessing risk, and managing limited resources, and that’s exactly what you do in business. When I played poker, it was my own money on the line—I was essentially bootstrapping my poker career. That same mentality applied when bootstrapping Whippy. Every decision is like a calculated bet, weighing potential outcomes against the investment. You need to think about short-term ROI but also the long-term tournament strategy—when to go all in, when to fold, and when to take calculated risks.
Another key skill I took from poker is avoiding emotional decision-making, or what we call "tilt." In business, you’ll face setbacks—deals fall through, competitors make moves, markets shift. The worst thing you can do is react emotionally instead of strategically. At Whippy, we approach decisions with a risk-reward framework, using expected value calculations to make the best call based on the information we have at the time.
Could you share the origin story of Whippy AI? What specific problem or opportunity did you identify in business communication that led you to found the company in 2020?
Whippy started with my co-founder, Jack Kennedy, and me running a web development agency. We used it as a way to get under the hood of various businesses, identifying operational inefficiencies and bottlenecks. One problem stood out: businesses were losing money due to broken communication. They weren’t following up with leads consistently, weren’t using omnichannel outreach, and were essentially leaving revenue on the table.
We initially built a simple web lead form that integrated with SMS to help businesses close that communication gap. But as we dug deeper, we realized the need was much larger—companies needed a full-fledged messaging and automation platform that could handle SMS, email, and now, AI-powered voice interactions. Today, Whippy has evolved into an end-to-end business communication solution, and our Voice AI product, in particular, is what’s really making waves.
Whippy AI handles tens of millions of conversations monthly across multiple channels. What technological breakthroughs or innovations have enabled you to scale the platform so effectively?
Scaling Whippy to tens of millions of conversations per month came down to two major factors: infrastructure and optionality.
When we started with SMS, we quickly realized that being tied to a single carrier aggregator was a massive risk—if they had issues, we had issues. So we became one of the first platforms to integrate with multiple carriers, optimizing deliverability across different networks. We applied the same approach to AI. Instead of relying on a single LLM, text-to-speech model, or voice provider, we built a flexible infrastructure that lets us dynamically switch between different models based on the use case. This adaptability allows us to offer clients a tailored solution while also ensuring we’re not bottlenecked by a single technology provider.
Scaling isn’t just about handling volume; it’s about building a system that’s resilient, adaptable, and optimized for performance.
How do you balance automation with maintaining authentic customer experiences? What principles guide your approach to creating AI agents that truly represent a brand's voice?
One of the biggest lessons I’ve learned is that simplicity in user experience drives adoption. My dad is a doctor, and he uses Whippy—the front desk staff needs to be able to build AI agents without technical expertise. If an AI system is too complex to configure or maintain, businesses won’t use it, no matter how powerful it is.
We designed Whippy with a uniform UI across all products, making it seamless to integrate AI into existing workflows. From a conversational standpoint, the AI agents we build are designed to maintain brand voice alignment, context awareness, and seamless human handoff. AI should enhance human interactions, not replace them. The best AI-powered experiences feel natural, not robotic.
You've had success across diverse industries from gaming to floristry with BloomNation, and now AI with Whippy. What common principles have you found that contribute to business success regardless of industry?
No matter the industry—poker, floristry, or AI—the core principles of success remain the same: hunger, hustle, and resilience.
People love to romanticize ideas, but execution is what matters. A great idea is 1%, execution is 99%. In poker, you can’t dwell on bad beats; you have to reset and focus on the next hand. In startups, you will hit roadblocks—funding challenges, product setbacks, hiring missteps. The ability to keep pushing forward, iterate, and adapt is what separates winners from the rest. Passion and perseverance, even in the toughest moments, are the real differentiators.
With Whippy saving over 40,000 hours of work monthly, how do you advise companies to redirect this newly available human capacity? What's the most innovative use of "freed-up time" you've seen from a client?
When AI frees up time, the biggest ROI comes from reallocating resources toward revenue-generating activities.
One of the best examples is in recruiting. Traditionally, recruiters waste hours manually screening resumes, playing phone tag, and engaging with unqualified candidates. With Whippy’s Voice AI, companies can instantly engage applicants, conduct multilingual screenings, and auto-fill their database with key candidate insights. This allows recruiters to focus on higher-value tasks like closing top talent.
In industries like healthcare, we see AI handling routine patient outreach, which lets staff spend more time on critical patient care. It’s all about shifting human effort to where it’s most impactful.
The AI landscape is evolving rapidly. How do you stay ahead of competitors and continue innovating at Whippy? What developments are you most excited about for the future of business communication?
One of Whippy’s biggest competitive advantages is our multi-product ecosystem.
We don’t just offer Voice AI—we have messaging, automation, and soon, VOIP. This interconnected system creates compounding value across products. For example, when our Voice AI identifies a lead that needs human follow-up, it can seamlessly live transfer to an available rep on our VOIP system. Meanwhile, our messaging platform captures that conversation history for future interactions.
By continually expanding our infrastructure and building products that strengthen each other, we stay ahead of competitors who focus on isolated AI solutions.
You've mentioned Whippy works extensively in healthcare, staffing, legal, and real estate sectors. Are there particular challenges or opportunities unique to implementing AI solutions in regulated industries?
Regulated industries like healthcare, staffing, and legal come with unique challenges, but also massive opportunities.
One key aspect is ensuring AI compliance with opt-in and transparency requirements. For example, in staffing, when an applicant applies for a job, they’ve expressed intent to be contacted. This makes AI-driven outreach highly effective—candidates will engage with AI-driven screenings for over 30 minutes because they want the job.
Compare this to outbound AI cold calling, where businesses risk compliance issues and negative consumer perception. The key to AI adoption in regulated industries is leveraging AI where engagement is welcomed rather than forced.
Looking at the broader AI industry, what trends do you believe are overhyped, and which underappreciated developments might significantly impact how businesses operate in the next 5 years?
Overhyped trends include the belief that AI will completely replace humans. The reality is that the best AI systems don’t eliminate jobs—they shift human effort toward more meaningful, revenue-generating work. Another overhyped area is the idea that AI can independently create truly innovative, original content. While AI can enhance creativity, it still lacks the ability to generate groundbreaking ideas on its own.
Underappreciated trends include AI-first workflows, where businesses integrate AI at the core of their operations instead of layering it onto existing processes. AI’s biggest impact will be in frontline industries like staffing, logistics, and healthcare, where real-time decision-making is crucial. Another overlooked area is AI-powered decision support—beyond automating tasks, AI’s real power lies in providing businesses with insights at the right time to improve their decision-making.
The next five years will redefine how businesses communicate, and Whippy is positioned at the forefront of that transformation.
As the AI landscape continues evolving, Daneshgar positions Whippy at the intersection of innovation and practicality. By creating AI systems that enhance rather than replace human interactions, Whippy empowers businesses to redirect human capacity toward revenue-generating activities. The company's multi-product ecosystem—spanning Voice AI, messaging, automation, and soon VOIP—creates compounding value that separates it from competitors focused on isolated solutions. With regulated industries like healthcare and staffing embracing these technologies, Daneshgar envisions a future where AI-first workflows redefine business communication. Through hunger, hustle, and resilience—principles that have guided his success across diverse industries—Daneshgar and Whippy AI continue pushing the boundaries of what's possible in business communication technology.