Welcome back. I hope you missed seeing this in your inbox, because I know I missed writing to you.
Have so much to catch you up on.
First, mark your calendars. We're taking Money Memories on the road with two live recordings: Los Angeles on August 6 and San Francisco on August 17. And this week, we're hosting an event for LPs and GPs in Manhattan Beach. RSVP here. Come say hi in person.
Now, the recap. I served as emcee for 500 Global in Tbilisi, Georgia, and got to experience the magic of the region, connecting with incredible founders from Kazakhstan, Uzbekistan, and Ukraine.
In London, I took the stage with Xero at Xerocon to demystify the AI lingo that keeps SMBs scared to make moves. In between, I had an emotionally impactful visit to Belfast, where seeing the lasting divide of the Troubles reminded me that there are still places technology cannot reach.
Gates in Belfast, Northern Ireland separating Protestant and Catholic communities.
Oh, and we officially kicked off fundraising for Armada. We have a brilliant, all-star team of women (like you had a doubt), verbal commits, and we're ready to reach our $2M first close. Interested in learning more? Fill out this form.
Can't wait to share more in my coverage. But first, let's pick up with 5 Questions, featuring a founder building in sports, an area I've covered before.
Doculingo’s Taylor Wrice
5 QUESTIONS WITH TAYLOR WRICE
1. What’s the problem you saw that others underestimated — and how did it first show up in your own life or work?
My experience in both the Department of Defense and Revenue Operations gave me a unique perspective on a problem that most organizations underestimate: information fragmentation. In government and defense environments, I saw how critical decisions depended on accurate information moving across teams, systems, and stakeholders.
Later, working in Revenue Operations, I encountered the same challenge in the private sector. Sales, finance, customer success, legal, and leadership teams were all operating from different applications, documents, spreadsheets, and workflows. Everyone had part of the story, but no one had the complete picture. The result was operational silos, slower decision-making, compliance risks, lost productivity, and missed revenue opportunities.
As organizations became increasingly global, these challenges expanded across languages, countries, and regulatory environments.
What started as a recurring observation in both government and commercial settings became the foundation for Doculingo.
We built the platform to help organizations break down information silos, unlock intelligence from their documents and workflows, and operate more effectively across borders, departments, and stakeholders.
We’re not in the “document” business.
Stop being the middleman between your own finance tools.
Most finance teams work on five different tools and a prayer. Ramp replaces all of it: corporate cards, bill pay, expense management, travel, and procurement. AI-powered with real-time visibility and real control.
2. What category do people most often mislabel you as — and what’s the truth?
People often categorize us as legal tech or a document intelligence platform. That’s understandable because documents are where many of our workflows begin.
But the reality is we’re building operational infrastructure for global organizations. Documents, contracts, translations, compliance, reporting, and workflow automation are all connected pieces of a much larger challenge: helping organizations move information, decisions, and opportunities across teams, systems, languages, and borders.
We’re not in the document business. We’re in the business of helping organizations operate globally with less friction.
3. What is a decision the company made that slowed growth or limited optionality in the short term, but ultimately strengthened the business model or customer trust over the long term?
Rather than chasing broad adoption, we focused on solving mission-critical workflows for organizations. We turned down opportunities to become a generic AI tool and instead concentrated on high-trust environments where contracts, compliance, operations, and cross-border collaboration matter.
That decision slowed top-of-funnel growth because it required longer sales cycles and deeper customer engagement. However, it helped us build stronger relationships, higher conversion rates, and a platform customers rely on for core business processes rather than experimentation. In the long run, trust has proven more valuable than rapid but shallow adoption.
4. What's the most expensive thing you had to unlearn as a leader?
I had to unlearn the belief that I needed to have all the answers. Coming from athletics, government, and operational leadership roles, I was conditioned to solve problems myself.
As a founder, I learned that growth comes from creating clarity, empowering others, and attracting people who are better than you in specific areas. The cost of that lesson was time.
The moment I stopped trying to be the smartest person in every room and focused on building the right team, partners, and advisors, the company will accelerate even more.
Growth comes from creating clarity.
5. Share one metric, study, or real-world data point that validated (or disproved) your original thesis.
Our strongest validation came from customer behavior rather than a market study.
We saw approximately 67% of our pilot customers convert into paying customers. That told us the problem wasn’t whether organizations saw value in streamlining contracts, compliance, translation, and operational workflows and it was whether we could get them to experience the platform firsthand.
The conversion rate validated our belief that organizations operating across departments, systems, and geographies need a better way to unlock and act on the information trapped inside their documents and workflows.
If you’d like to be featured in an upcoming 5 Questions, reply to this email. In the meantime, here’s how you can support Bear and the Bull:
🤝 Become a sponsor and reach a curated audience of tier 1 VCs, tech founders, and operators - here’s our media kit.
🔓 Upgrade to become a paid subscriber to access my curated early stage market maps and list of early stage investors and companies.
Till next week,
Ilona
P.S. Interested in working with me as a speaker or moderator? Hit “reply” to this email.
Bonus for paid subscribers: What’s one piece of advice you wish investors understood about building in your category?
Subscribe to our premium content to read the rest.
Like what you have read so far? Become a paid subscriber to access the full archive, exclusive deep dives, market maps, and insights from founders and operators at the cutting edge of innovation.
Upgrade