Playbook: 5 Insider Tactics That Win Investors Over
Let's be honest: preparing for investor due diligence can feel like preparing for a job interview where you're not sure what questions they'll ask, but you know you need to be prepared to sell your story. After working with hundreds of founders through their fundraising journeys, we've noticed a pattern - the difference between founders who navigate due diligence with confidence and those who feel overwhelmed comes down to how they approach their answers, not just what they know.
Early in the Spring, Volition Advisor, Nadia Ladak, Co-Founder and CEO of Marlow, led a session for the RBC Women in Cleantech Accelerator (MaRS Discovery District), as part of our Data Room Masterclass Series, sharing practical strategies for navigating tough investor conversations. Here are five game-changing insights that can transform your next due diligence meeting from an interrogation into an opportunity.
1. Turn Negatively Framed Questions Into Your Strongest Selling Points
We've all been there. An investor asks, "Why wouldn't [ABC competitor] just copy your product and crush you?" and suddenly you feel defensive. Your instinct might be to argue why they're wrong, but that defensive energy rarely wins investors over.
Instead, take a breath and reframe the question. What they're really asking is: "What's your competitive advantage?" or "How will you defend your market position?"
Nadia shared her own experience: "When investors ask, 'Why wouldn't Tampax just copy your lubricated tampon?' I could get defensive. Instead, I reframe it to talk about our patent strategy, our first-mover advantage, and how we're positioning ourselves as an attractive acquisition target."
By consciously reframing these questions, you control the narrative and showcase strategic thinking; a skill that comes in particularly handy when facing “prevention-based” questions.
2. Sell the Vision, Not the Shopping List
Here's a common mistake: when investors ask about use of funds, founders often respond with a generic list: "40% for team, 30% for marketing, 30% for R&D." While accurate, this misses a huge opportunity to get investors excited about your future.
Instead, talk about specific milestones their investment will unlock. Rather than "we need money for marketing," try: "This funding will allow us to run our first national campaign, which will acquire 10,000 customers and validate our CAC assumptions before Series A."
The difference? The first approach sounds like you're asking for money to keep the lights on. The second shows you're strategically building toward measurable outcomes that increase company value.
3. Own Your Pivots (They're Actually a Strength)
Many founders hide their pivots and mistakes, thinking investors want to see a perfect track record. In reality, investors know that no startup journey is linear–they want to see your ability to learn and adapt.
During the session, Nadia shared how she tested different channel strategies: "When we first launched, Shopify was our only channel. It wasn’t taking off in the way we wanted to but launching on Amazon has opened up an entire new market for us..."
This transparency accomplishes two things: it shows you listen to customers and adapt quickly, and it demonstrates the kind of founder investors want to back: one who can navigate challenges rather than be derailed by them.
4. Answer the Question Behind the Question
Every investor question has a subtext.
When they ask about your team, they're assessing execution risk. When they ask about competition, they're evaluating market dynamics. When they ask about customer acquisition, they're calculating unit economics.
The key is to address both the surface question and the underlying concern. If an investor asks about your burn rate, don't just give them a number. Explain how you're managing cash efficiently, what metrics you're watching, and how you'll extend runway if needed. This approach shows that you understand their concerns and can address them proactively.
5. Make Your Current Investors Your Best Sales Team
If you have existing investors willing to share their due diligence materials or investment memos with new investors, you've got gold. This isn't just about saving time (though it does)--it's social proof at its finest.
One founder in our session mentioned that having their lead investor share their deal memo cut their due diligence timeline from four weeks to two. New investors could see that someone else had already done the deep dive and found the opportunity compelling.
Don't be shy about asking your current investors if they'd be willing to share their materials or even make introductions. The best investors understand that helping you raise your next round increases the value of their own investment.
Working on turning those initial conversations into serious funding discussions?
Now comes the real work - turning those initial conversations into serious funding discussions. These strategies will help you navigate the due diligence process with confidence.
Let's transform connections into committed investors! Through our Capital Connect Program, you can work directly with advisors like Nadia who've been in the trenches and know exactly what investors are looking for. Learn more about the program and apply to get access to strategic guidance through 1:1 Startup Business Advising.
Remember: due diligence isn't about having perfect answers - it's about demonstrating the strategic thinking that makes investors want to join your journey.
About Nadia Ladak
Nadia is the co-founder and CEO of Marlow, a period care brand that is revolutionizing women’s health. The brand’s award-winning product is the first-ever lubricated tampon for smoother and more comfortable insertion. Nadia has raised $2.5M in funding to date and $700K in non-dilutive funding from the top grants and pitch competitions like Visa She’s Next and Pepsi Co Stacy’s Rise to fuel the brand’s growth. She is passionate about advocating for entrepreneurs and inspiring the next generation of entrepreneurial leaders. She leads the entrepreneurship alumni community at her alma mater, the Ivey Business School, is on the employer advisory council at Venture for Canada, and is an entrepreneur in Residence at Branksome Hall. Nadia has been recognized on the Forbes 30 under 30 list and as one of the Top 25 Women of Influence.
LinkedIn: linkedin.com/in/nadia-ladak/
