The Journey of a Startup Investor
Insights, Challenges, and Advice
Most founders dream of securing venture capital funding, but what do investors really look for? We sat down with Jason Kean from True Vine Capital Partners, a firm that backs growing businesses at Pre-Series A and Series A.
Jason didn’t start in finance—he studied chemical engineering before making his way into investment management. Along the way, he discovered a passion for startups and venture capital, seizing opportunities that led him to where he is today. Now, he spends his time evaluating pitches, analyzing financials, and identifying businesses with real potential.
In this conversation, Jason shares what makes a startup stand out, the mistakes founders often make when pitching, and why brand loyalty doesn’t matter as much as delivering real value.
Omni: Thank you for joining us today. To start, could you share your journey and how you ended up in the field of investments?
Jason: Sure, it’s actually a story of luck and taking chances. I graduated from Taylor’s University with a degree in chemical engineering, a field that’s completely different from what I do now. But I’ve always loved numbers. My first job was at an insurance provider as part of their management trainee program.
I had a clear goal: to enter the investment world.
From the very beginning, I had a clear goal: to enter the investment world. During the program, I managed to make my way into investment management, specifically focusing on bonds. That’s where I developed an interest in company due diligence and financial analysis.
As part of the management trainee program, we were required to attend training at the Asia Business School under their foundational enrichment program for financial institution graduates. It was during one of these sessions that I met the founder of PolicyStreet, [Wilson]—if I remember correctly—and his talk really inspired me.
Omni: What about his talk that inspired you?
Jason: He shared insights about startups and entrepreneurship. At the time, many of my peers didn’t fully grasp the concepts he was talking about, but I found myself deeply intrigued. I already had some experience with startups—I had started four small ventures while in college—so his talk resonated with me. He noticed that I had a solid understanding of the startup ecosystem and approached me to collaborate on a project for a tech association. That project marked the beginning of my journey into this field.
From there, opportunities kept coming. One of my current partners took notice of my work and invited me to assist him with due diligence on a part-time basis. Over the years, that collaboration grew into something more permanent. Looking back, it feels like a mix of preparation, connections, and some good fortune along the way.
Omni: That’s an incredible journey! Let’s dive into your approach. When evaluating a startup pitch or business idea, what’s the first thing you look at?
Jason: Financials—always the financials. They tell a lot about the business.
Omni: So you go straight to the numbers?
Jason: Exactly. No fluff or flowery presentations—just the financials. If a startup has a strong unique selling proposition (USP), it will reflect in their numbers. Financials justify the USP because good traction will translate into strong figures.
Omni: Interesting. When you say traction, do you prioritize speed or lifetime value?
Jason: That depends on the stage of the startup. In the early stages, speed is crucial. Momentum is key to creating value and proving demand for the product or service. Later on, we shift focus to metrics like lifetime value (LTV) and customer acquisition cost (CAC). At that stage, it’s about measuring efficiency and sustainability rather than just speed.
Omni: Let’s talk about churn rates and customer loyalty. Given that brand loyalty is becoming less common today, what’s an acceptable churn rate for investors like yourself?
Jason: To be honest, I don’t pay much attention to churn rates because I don’t believe in brand loyalty. It’s all about value. If your service offers consistent value and outperforms competitors, customers will stick with you regardless of loyalty. If not, they won’t. So instead of focusing on churn rates, I focus on whether the product or service delivers real value to the customer.
Omni: What are some common mistakes you see startups making when pitching their ideas?
Jason: There are two major issues I see repeatedly:
Problem Statements Are Too Broad: Many startups try to tackle huge issues but fail to narrow their focus or offer specific solutions. For example, someone might say they’re solving diabetes with a management system but fail to explain how their solution directly addresses the needs of diabetic patients. It’s important to have a clear and niche focus that delivers tangible value.
Misaligned Incentives: Startups often design solutions without aligning them with what customers actually need or want to pay for. For instance, if you’re creating a subscription-based app for diabetes management, why should a customer pay for it if they still need to spend money on testing strips or medication? Unless your app proves it can save them money or reduce their reliance on strips or medication, there’s no clear incentive for them to adopt it.
Omni: Do you think accelerators are addressing these issues effectively?
Jason: I believe there is room for improvement locally. Accelerators tend to focus on pumping knowledge into startups during their programs but fail to provide meaningful post-graduation support. There’s a need for some form of follow-up or strategic pairing with corporates to help startups scale or implement their solutions.
We can learn from more comprehensive accelerators in places like France are much more cohesive. They actively involve corporates and create opportunities for startups to adopt their solutions in real-world scenarios.
Omni: With the availability of startup programmes, startups still make these mistakes post-program. Where does the problem lie—on the founder’s side or the programme side?
Jason: It’s a bit of both. On one hand, some founders are resistant to change because they’re overly confident in their ideas—they’ve won competitions and received validation from peers, so they struggle to accept constructive criticism about their business model.
On the other hand, some programmes don’t provide enough practical value beyond basic knowledge-sharing. For example, I’ve seen accelerators offer deals that offers very little money for a substantial stake at an early stage—that doesn’t make sense! Diluting ownership too early can hurt founders in the long run!
Omni: It’s interesting that you brought that up, let’s talk about valuations—how should early-stage startups approach this topic?
Jason: Forget about valuations in the early stages! Focus on building a product first, testing it, getting paying customers, and improving your offering based on feedback. Only then should you approach investors.
Too many startups pitch ideas without even having proof of concept (POC). It’s like asking investors to gamble on a dream rather than on a viable business.
Omni: But what if founders don’t have the resources to build a solution without funding? How do they get past this chicken-and-egg situation?
Jason: Great question! My advice is to start as unscalable as possible—even if it means solving problems manually/primitively at first. For example you envisioned a service that has an app or payment gateway for a personalised service. You could offer the service to a small test market and get paid manually.
If people are willing to pay for your service—even in its most basic form—you’ve validated your idea and proven there’s demand for it.
If people are willing to pay for your service—even in its most basic form—you’ve validated your idea and proven there’s demand for it. Once you have paying customers, then you can scale up by investing in technology or automation.
Omni: That’s excellent advice! To wrap up, what are two key pieces of advice you’d give to aspiring startup founders?
Jason: First, define your USP clearly and make sure it’s relatable enough for both customers and investors to understand its value. Second, avoid focusing too much on valuations or giving away large equity stakes too early—build something sustainable first before approaching investors.
Omni: Thank you for sharing these valuable insights! This has been an eye-opening conversation.
Jason: My pleasure—thank you for having me!
Jason’s journey into venture capital is a reminder that opportunities often come from unexpected places—but what matters is recognizing them when they do. His insights cut through the noise of startup hype, bringing the focus back to fundamentals: strong financials, a clear USP, and real customer value.
For founders navigating the fundraising landscape, his advice is simple—build something sustainable first, then seek investment. And if you’re still figuring things out, don’t be afraid to start small and unscalably.
If you’ve had an unconventional path into startups or investing, we’d love to hear your story. Reach out—we’re always up for a good conversation.