Building Relationships with Investors: Advice from Seasoned Entrepreneurs

First-time founders often try to impress investors instead of earning their curiosity.

The shift happens when you stop asking for capital and start sharing progress that shows clarity. We found that consistent founder updates, not cold intros, built stronger relationships. When an investor sees how you execute between meetings trust compounds over time.

One client we worked with sent short monthly snapshots showing real users, not forecasts. That single habit changed the tone of every conversation from persuasion to partnership.

The best strategy is to build in public. Investors follow consistency more than hype. Relationships grow faster when updates show traction instead of talk.

Being the Partner at spectup, the single most important advice I give first time entrepreneurs about investor relationships is to stop thinking in terms of pitching and start thinking in terms of trust building. Early in my career, I made the mistake of approaching investors only when capital was urgently needed, and the conversations felt forced on both sides. What changed everything was realizing that investors respond better to clarity, consistency, and honest progress over time than to polished urgency.

One time, while helping a founder prepare for fundraising, we encouraged them to start conversations months earlier with no ask attached. They shared what they were building, what was not working yet, and what they were learning. Those early touchpoints made the actual funding discussion feel like a continuation rather than a cold start.

The strategy I’ve used consistently at spectup is structured but human outreach. Research investors properly, understand what they care about, and approach them with relevance, not volume. Keep updates short, transparent, and predictable. Investors appreciate founders who communicate like operators, not salespeople.

I also recommend founders avoid overselling. Confidence comes from knowing your numbers, your risks, and your next milestones. One of our team members often says that investors invest in how founders think under pressure, not just in the idea. That has proven true repeatedly.

Finally, remember that relationships compound. Even a no today can turn into a yes later if handled well. Treat every interaction as a long term conversation. Funding is an outcome of trust, not the starting point.

The most important advice I’d give first-time founders is to start building investor relationships early, and to see them as long-term, not transactional. Investors respond far better when you’re clear on your story, consistent in how you communicate, and engaging well before you actually need capital. In my experience, fundraising works best when it’s structured and intentional. Instead of high-volume cold outreach or constantly tweaking your deck, it’s far more effective to know exactly who you want to apply to, have a single, well-thought-through narrative, and a clear way to manage investor conversations. That leads to better discussions, clearer feedback on what’s landing, and far less time lost on admin, so you can stay focused on building the business.

As an investor, here’s my advice: do your homework before you reach out, know exactly what that investor funds, and respect that their priorities are usually clear and immovable. You can’t argue someone into changing their investment strategy, but you can earn attention by showing true alignment and asking smart questions: What are you prioritizing right now, how many investments are you making this year, and what does a great founder-investor partnership look like to you?

Treat it like sales with integrity: lead with relevance, not hype, and make it easy for them to say “yes” to the next step. If you’re seeking venture funding, have a thorough data room ready before the first serious conversation, because every time I have to ask for basic materials that aren’t at your fingertips, confidence quietly drops. Venture capitalists need to believe in the possibility of a 10x return in 5-7 years, so show evidence you can grow that fast: traction, retention, a clear go-to-market engine, and the numbers that back your story. And be unmistakably clear about your exit strategy, including who could acquire you and why you’d be valuable to them.

The strategy I used was simple: warm introductions when possible, crisp outreach when not, and conversations that centered curiosity and fit rather than a hard ask. Because the best investor relationships aren’t transactions, they’re trust built through preparation, clarity, and follow-through.

Founders have always assumed the earliest stage of building an investor relationship is to create a pitch deck, but trust between founders and investors develops much earlier through collaborative problem solving. The most meaningful indicator for investors does not come from vision language, but how you think on your feet. For me, there were months of narrowly focused, technical discussions about data latency thresholds, cost ceilings and failure scenarios that can cause systems to fail. These conversations illustrated my ability to reason well prior to any discussion about funding.

When meeting with investors, I did not engage in broad outreach; instead, I met with five individuals who either had developed or invested in infrastructure at similar scales. Each engagement was based on a single tangible system decision and the trade-offs associated with that decision versus a narrative of the future. Investors remained engaged because they were able to participate in the actual process of thinking as opposed to a presentation. Founders need to treat early conversations with investors as work sessions where clarity is better than enthusiasm. Once the confidence in the founder’s execution discipline and decision making has been established, funding will follow.

The most important advice is to build relationships with investors long before you need to raise money.

For first-time founders, the biggest mistake is treating fundraising as a transactional process. Investors are more responsive when they have context over time, not just a cold pitch when you need capital. I focused on sharing progress, not asking for money. That meant short updates on what we were building, what was working, what wasn’t, and how we were thinking about the market. When the round came together, those conversations were already warm.

In terms of strategy, I prioritized targeting the right investors over the most famous ones. I looked for people who had experience in AI, SaaS, or marketplace-style businesses and who had backed companies at a similar stage. Warm intros helped, but clear thinking and traction mattered more than perfect decks. Every conversation was treated as a chance to learn, not to sell.

My recommendation is to be honest, concise, and consistent. Do not oversell or hide risks. Investors are evaluating how you think as much as what you are building. Strong relationships come from trust, and trust is built by showing up prepared, following through, and communicating clearly even when things are not going perfectly.

Treat investors like future customers: show the product, real usage, and why people choose it. When we raised our first angel round, we skipped glossy decks and walked investors through live product data to prove traction and answer questions inside the product. I recommend preparing a crisp demo with up-to-date metrics so the discussion centers on proof rather than projections.

The most important thing for first-time entrepreneurs to remember is to establish relationships with potential investors prior to actually requiring capital. The most beneficial conversations with potential investors happen when money is not the most important aspect of the discussion. This allows both parties to continue to communicate openly and receive feedback about their ideas or projects without being under pressure from a funding timeline.

The way I put this into practice was to build those relationships with potential investors by treating them as a resource, not just a funding source. I focused on telling investors the challenges I faced as an entrepreneur, but also where I had gained traction. By being open and honest with potential investors about my business and my need for support, I began to build trust. Throughout the process of applying for investment dollars, I continued to communicate with potential investors by sending them periodic updates regarding the progress I was making in building my business, even though they had not yet invested in my business.

When it comes time for founders to seek funding, my advice is to know your key metrics in advance, know your numbers backwards and forwards, and recognize that building long-term relationships with potential investors should be a gradual process. Investors are going to back entrepreneurs that they can trust and entrepreneurs that are going to execute on a consistent basis, as opposed to just being able to provide them with a strong pitch deck.

One piece of advice I would give first-time entrepreneurs is to focus on building credibility before you ever ask for capital. Investors are backing people as much as they are backing ideas, and trust is built over time, not in a single pitch meeting.

When approaching potential investors, I focused on having thoughtful conversations rather than leading with a funding ask. I made sure I understood what each investor cared about, shared real data and progress, and was honest about both opportunities and risks. That approach led to stronger relationships and more productive follow-ups. For anyone seeking funding, my recommendation is to stay consistent, be transparent, and treat investor relationships as long-term partnerships. The strongest outcomes usually come from relationships that were built well before money was on the table.

I’ll give you the advice most first-time founders don’t want to hear, but need early: If you’re chasing investors for money, you’re already losing the relationship.

I’m Bryce North, Founder and CEO of Don’t Be A Little Pitch (DBALP). Before PR became my world, I spent years building and scaling companies and working around venture and angel capital. Founder, advisor, operator. I’ve seen how these relationships work from multiple angles.

What I learned early is that investors are rarely persuaded by enthusiasm alone. They’re paying attention to how clearly you communicate, how well you understand your own business, and whether you can create momentum without constant validation. Confidence shows up in execution, not in polished decks or big promises.

When I approached investors, I focused on relationships first. That meant having conversations without pressure, being honest about where the business actually was, and showing steady progress over time. I didn’t lead with asks. I led with clarity and follow-through. Trust was built because the story stayed consistent and the work backed it up.

I never led with money. I led with momentum.

That meant:

1. Building brands people already recognized before I asked for capital

2. Using media, speaking, and third-party credibility to establish authority early

3. Treating investor conversations as long-term relationships, not transactions

When investors see you consistently showing up, owning your narrative, and executing in public, the dynamic shifts. The conversation moves from “convince me” to “tell me more.”

For founders seeking funding now, my advice is simple: Get good at telling your story before you ask anyone to believe in it. If you can clearly articulate what you’re building, why it matters, and how you think, investors are far more likely to lean in.

Get visible before you get funded. Investors are pattern spotters. Capital follows clarity. It always has.

The most important advice I’d give first-time entrepreneurs is this: don’t approach investors as gatekeepers, approach them as potential partners. The way you frame that relationship from the very first conversation determines whether you build collaboration or invite control.

I learned this early while raising capital, when we sat across from a Tier-1 VC for the first time, we felt the familiar itch of the “pitcher-catcher” dynamic. We polished numbers, projected certainty, and performed for approval. Halfway through, it became clear: we were treating a partnership like a job interview.

That mindset creates what is known in behavioural terms as a ‘Power Asymmetry Trap’. When founders show up “below” an investor, they invite micromanagement instead of collaboration. To build a resilient company, we had to stop pitching and start contracting at eye level.

We learned to engage on three layers: transactional (the baseline terms), emotional (how we handle the dark days), and expectational (sharing a roadmap instead of “selling a dream”). Over-promising creates an ‘Expectation-Reality Gap’; under-delivery from a founder activates the investor’s brain, processing it as a loss, and eventually, erodes trust.

We found that maintaining an “eye level” relationship requires the courage to say “I don’t know.” Paradoxically, admitting a gap in your knowledge increases your perceived authority. It signals that you are a rational operator, not a desperate salesman.

When we engage potential investors, we use a “Co-Founder Lite” approach:

1. Bring a real problem, not just a deck. We watch how they think. If they lecture us, they’re a boss; if they brainstorm, they’re a partner.

2. Lead with risks. By being the first to point out the holes in our boat, we radically prove we’re the best people to plug them.

3. No pedestals. We remember that while they have the capital, we have the “alpha”, i.e. the unique insight and the execution.

The moment you stop trying to “get” an investor to invest and start “inviting” them to build, the power dynamic shifts. You don’t want a master; you want a passenger who’s willing to help change the tire at 3 AM.