Jason Kirby: Hey, everyone. Welcome back to Fundraising Demystified. Today, we have Alon Talmor with us from Ask AI. Welcome to the show.

Alon Talmor: Hey everyone, happy to meet you.

Jason Kirby: I’m really excited to have you on the show today. You have an impressive serial founder background and technical depth, and I’m excited to learn about your story and what you’re doing at Ask AI. Can you tell the audience what you’re building at Ask AI and a bit about your background?

Alon Talmor: Perfect. I’ll start from the beginning. I’m a second‑time founder—our previous startup was sold to Salesforce. We were acquired in 2012. That company, BlueTail, did something that in today’s Ask AI would be just a single app in a broader suite: we aggregated information from the web about a prospect and presented it—like a LinkedIn on steroids. Back in 2012 that was pretty new; it still seems needed today. Post‑acquisition, I opened Salesforce’s Tel Aviv office and served as Chief Data Scientist. In 2015, when my vesting ended, I did something unusual for a founder: I started a PhD in AI/NLP to understand where the future was heading.

Alon Talmor: I was lucky to meet a professor returning from Stanford to lead NLP efforts at Tel Aviv University. Back then, AI was nothing like what we see today with ChatGPT. “Deep learning” was the buzzword, mostly applied to computer vision. We witnessed the revolution unfolding—our group received a best paper in 2019 alongside authors of BERT, a foundational language model. In 2020, as I finished my PhD, we realized something big was coming with generative AI and launched Ask AI.

Alon Talmor: Our focus wasn’t to become a foundational model company—even though we had professors and PhDs onboard—but to build solutions around generative AI. We see generative AI like the personal computer: it will make everyone more productive, but it’s not obvious how, especially in industry. In the early PC era, people learned to code and played games; only when Windows and Office arrived did companies buy computers for every employee. We want Ask AI to be the second thing you buy for each employee: a real AI helper—an AI sidekick—to empower, not replace, people.

Jason Kirby: I can see how you raised money—you do a great job telling the narrative. Leaving Salesforce to pursue a PhD is uncommon for founders. What did people around you say when you made that decision?

Alon Talmor: Mostly that I must be bored! In reality, my co‑founders from BlueTail all started successful companies (Placer AI, Plank, and Fungard). I was looking for a technological breakthrough to truly disrupt industry—and there was something romantic about pursuing a PhD; my father did one, and I had started in brain science before my first company but didn’t finish. I traveled for a year in 2015–2016, then met Professor Jonathan Berant returning from Stanford. He initially asked why he should work with me—I had no academic credentials then—but I persuaded him and was thrilled to work together.

Jason Kirby: Going back to BlueTail—what was the market like? From 2009–2012 the market was tough. How did you build and sell to Salesforce so quickly? Did you raise capital, and how is then versus now?

Alon Talmor: It was hard. I’m a “crisis‑time” founder: BlueTail during 2008–2009; Ask AI in 2022–2023 turbulence. Back then, SaaS was less mature, sales were face‑to‑face (no Zoom), and everything felt old‑school. We bootstrapped—did data science consulting—and built the product three days a week. My co‑founder and I flew to San Francisco to sell to early customers; Marketo was one of the first. We reached a few hundred thousand dollars ARR before fundraising. While seeking a Salesforce partnership, they decided to acquire us. Fundraising amounts then were nothing like today.

Jason Kirby: After the sale, what’s that transition like—moving your team and product into a big company?

Alon Talmor: Not easy. Even then, Salesforce was big. We were its first external location outside the Bay Area. Corporate life requires patience; impact is slower. For me, that was challenging.

Jason Kirby: Let’s energize everyone. You’re building Ask AI—at what point did you decide you’d need outside money, and how did you raise it?

Alon Talmor: In 2020 there was no generative‑AI hype—ChatGPT only arrived in November 2022—so we didn’t sell “gen AI.” We framed it as enterprise search with “Google‑like answers.” We started with design partners before raising. I self‑funded initial months to build a prototype. With early validation, we formally raised and opened the company at the end of 2021.

Jason Kirby: How did you define “validation”?

Alon Talmor: Pick a substantial stakeholder, listen first, and confirm the need before pitching. Then ship a prototype and look for love—high CSAT and real usage. For example, at design partner Yotpo (~800 people), the VP of Delivery described complex, long‑tail product questions overwhelming success and support—far beyond “chatbot” FAQs. We saw this pattern across PLG companies with deep documentation: if unanswered, it creates internal friction across support, success, Slack channels, even product. That pain existed before we built the solution—strong signal to proceed.

Jason Kirby: Once validated, you formalized and raised at peak 2021. Walk us through the process and timeline.

Alon Talmor: I looked for a COO to join full‑time after a round. We began fundraising together; I introduced him to investors. Mid‑process, he got a promotion and backed out. That created a major issue—the narrative changed mid‑round. I had to work day and night to complete it. Being transparent with our lead (State of Mind Ventures) was critical; I told them exactly what happened. Trust matters more than gloss. They continued, asked me to find a co‑lead, and I ultimately closed with Vertex Ventures as co‑lead—finalized at the last moment.

Jason Kirby: How many investors did you engage to make it happen?

Alon Talmor: Surprisingly few. We focused on two to three strong options rather than a broad spray. It’s better to build deep chemistry with a small set than to dilute attention across dozens.

Jason Kirby: How did you target and get introductions?

Alon Talmor: Prioritize chemistry with the GP and a modern, founder‑friendly mindset. You want a board that backs you, not fights you. Look for partners who truly understand your product and pain, not just the “hot space.”

Jason Kirby: After the seed closed, what next?

Alon Talmor: We raised about $7M initially. In mid‑2022’s downturn, we added a ~$2M extension via SAFEs from strategic US investors—GTMfund, Interplay, and notable angels. I recommend a broader cap table at seed if you can manage the conversations—the network pays long‑term. Terms reflected growth at the time.

Jason Kirby: When and how did you approach the Series A?

Alon Talmor: We weren’t running a formal process. Leaders Fund invited me to a dinner—I almost skipped it—but the chemistry with David Stein and Gideon was immediate. We met daily that week and had a term sheet fast. It’s manufactured luck: keep meeting investors so timing and thesis eventually align. At Series A, customers must love you—great references are non‑negotiable. Good investors will call them without asking.

Jason Kirby: Did Leaders Fund take the whole round?

Alon Talmor: Along with pro‑rata from seed investors, yes—no extra room. We weren’t looking to raise an outsized round. Inflated valuations catch up with you unless revenue supports them.

Jason Kirby: Any mistakes you’d change?

Alon Talmor: Start building relationships with larger investors even earlier. You can’t begin too soon. Optimize for GP‑level relationships and periodic updates so they see your trajectory.

Jason Kirby: Parting advice for founders raising now?

Alon Talmor: Radical candor builds trust. Share the real picture early and often. Build a great business first; then raise from investors who’ve watched your progress over time.

Jason Kirby: Where can people learn more about you or Ask AI?

Alon Talmor: Our website has a memorable name—ask-slash-ai dot com—and you can reach out on LinkedIn. I’ll try to repost this episode as well.

Jason Kirby: Perfect—thanks for joining and for all the insights!

Alon Talmor: Thanks for having me—it was a pleasure.