The Art of the Fundraise: 8 Lessons from Redox Founder Luke Bonney
Fundraising advice is everywhere. Advice grounded in the experience of building a healthcare technology company, raising more than $100 million, and navigating multiple market cycles is considerably harder to find.
One of the advantages of the HealthX community is the opportunity for founders to learn directly from people who have already confronted many of the decisions they are facing. Over the years, we have brought experienced founders, operators, investors, and industry leaders together to share what they have learned (often with unusual candor).
In one HealthX founder bootcamp, Redox co-founder Luke Bonney shared lessons from building the healthcare interoperability company from its earliest days into an organization serving hundreds of customers and thousands of healthcare facilities.
His central message was that fundraising is not simply a financial transaction. It is a strategic process that affects a company’s ownership, leadership, culture, growth trajectory, and ability to fulfill its mission.
In this first article of a two-part series, we focus on Luke's practical advice for executing a successful fundraise, from crafting a compelling narrative and creating investor momentum to selecting the right long-term partners.
Here are eight lessons digital health founders should keep in mind.
1. Treat fundraising as the CEO’s primary responsibility
Luke’s approach to fundraising is deliberately concentrated: when it is time to raise, the fundraise becomes the CEO’s number-one priority.
A passive process (taking occasional investor meetings over many months) can feel less disruptive. In practice, it may consume more total time while producing a weaker result.
Fundraising is one responsibility that is especially difficult to delegate. Other leaders can support the process, prepare materials, organize data, and maintain company operations, but the CEO must communicate the vision and build investor conviction.
A focused process creates a clear tradeoff. The CEO will temporarily spend less time managing other parts of the business, and there may be issues to address afterward. But completing the raise efficiently allows the CEO to return to operating the company rather than allowing fundraising to remain a persistent distraction.
2. Remember that capital is not the scarce resource
Founders can enter a fundraise believing investors hold all the leverage. Luke encouraged founders to adopt a different perspective: the scarce resource is not capital. It is the limited number of companies compelling enough to produce venture-scale returns.
A strong company should not approach investors as though it is asking for a favor. It should approach the process with the confidence that it represents a rare opportunity.
That does not mean projecting arrogance or manufacturing artificial demand. It means understanding the value of the company, communicating it clearly, and running a process that reflects standards and intentionality.
Investors should feel that they are evaluating an opportunity other sophisticated investors may also recognize—not reviewing a company that will wait indefinitely for their approval.
3. Build one truthful story for every audience
The fundraising narrative should not exist only for investors. Luke recommended developing a story founders would be comfortable telling to:
Prospective investors
Existing investors and board members
Employees
Prospective hires
Customers and partners
A strong company has a single reality. The emphasis may change depending on the audience, but the underlying description of the problem, opportunity, strategy, and company performance should remain consistent.
This is particularly important in digital health, where the product itself may involve infrastructure, workflows, data exchange, reimbursement, or other subjects that do not immediately feel exciting to a generalist investor.
Redox, for example, could be described as healthcare “plumbing.” But the significance of the company becomes clear when interoperability is connected to what it enables: better tools for clinicians, better experiences for patients, and greater scale for companies improving healthcare.
Founders must translate technical capabilities into meaningful outcomes without overstating what the company has accomplished.
4. Show authentic conviction
Investors evaluate the market, product, team, financial performance, and competitive landscape. They are also evaluating whether the founders possess the conviction and resilience required to build something difficult.
That conviction cannot be manufactured by adopting a more enthusiastic presentation style. It comes from living with the problem, understanding it deeply, and genuinely believing the company has an opportunity to create something important.
The strongest pitches communicate:
Why this problem matters
Why it must be solved now
Why this team is uniquely equipped to solve it
Why the company can become significantly larger than it is today
Why the founders will continue working through inevitable setbacks
Passion alone is not sufficient. But when conviction is supported by insight and evidence, it becomes difficult to imitate and easy for investors to recognize.
5. Create velocity and a real timeline
A strong fundraising process creates momentum.
Luke often began a raise around a major industry event where he could schedule a high concentration of meetings within a short period. The specific event is less important than the principle: arrange enough conversations close together that investors move through the process on a similar timeline.
This makes it possible to communicate real deadlines.
Rather than vaguely saying the company is raising “this year,” founders can explain:
What the company is raising
What the capital will accomplish
When the process begins
When indications of interest are expected
When the company plans to select a lead or close the round
A timeline creates clarity for the company and urgency for investors. It also helps prevent the fundraise from stretching indefinitely.
The urgency must be authentic. Artificial scarcity is easy to detect. A well-organized process, however, naturally creates the conditions for investors to make decisions.
6. Practice with lower-priority investors first
Pitch quality improves through repetition. Founders tend to encounter a recurring set of investor questions. The first several meetings reveal which parts of the story are unclear, which assumptions will be challenged, and which metrics investors consider most important.
For that reason, Luke recommended ranking potential investors and beginning with those who are lower on the priority list. By the time founders reach the investors they most want on the cap table, they should have:
Refined the company narrative
Heard and answered the most common objections
Identified weak points in the presentation
Improved supporting data
Developed greater confidence
Potentially generated interest from other investors
This allows the company to enter its most important conversations with a stronger pitch and greater leverage.
7. Raise enough to account for uncertainty
A financial model may indicate that the company requires a specific amount of capital to reach its next milestone. Luke’s advice was to treat that calculation as a starting point, not necessarily the fundraising target.
Plans change. Sales take longer than expected. Healthcare implementations are delayed. Hiring costs increase. Regulatory, integration, or customer requirements emerge.
Companies should consider raising materially more than the minimum their model suggests, provided the resulting dilution and valuation remain responsible.
The objective is not to accumulate as much capital as possible. It is to ensure that the company has enough runway to reach the milestones required for its next financing from a position of strength.
Founders should also ask a forward-looking question: If we execute our plan, will this valuation allow the company to support a meaningfully higher valuation in approximately two years?
An inflated valuation can feel like a victory in the current round while making the next round significantly harder.
8. Optimize for investor quality, not only valuation
A lead investor may remain connected to the company for the remainder of its life. That makes investor selection one of the most consequential decisions in a fundraise.
Luke’s first criterion is what he calls the phone-call test: When something goes seriously wrong, is this the person the CEO will immediately call for help? Or will the CEO avoid the conversation and worry about how the problem will be presented at the next board meeting?
Every investor is supportive when the company is exceeding its goals. Founders need to know how an investor behaves when the company misses its numbers, loses an important customer, experiences a security incident, or faces another serious setback.
The best way to learn that is to speak with founders who have worked directly with the individual investor—not merely with the firm.
Luke recommended having at least three reference conversations and asking specifically about difficult periods.
Beyond the phone-call test, founders should look for a clear source of differentiated value, such as:
Relevant operating expertise
Customer or industry relationships
Recruiting capabilities
Follow-on capital
Market credibility
Experience scaling similar companies
Strategic insight during pivotal decisions
Luke noted that he did not always accept the highest available valuation. In several rounds, he chose an investor he believed was better for the company after getting the economics within an acceptable range.
Fundraising is a company-building discipline
The art of the fundraise is not the art of producing enthusiasm around a deck.
It is the discipline of communicating a compelling opportunity with honesty and conviction, creating a focused process, and selecting partners who can help the company achieve its ambitions.
But securing capital is only one part of building a successful venture-backed business. The decisions founders make about financing, governance, growth strategy, and culture can shape the company for years to come.
In the second article of our series, Luke shares seven additional lessons on building and scaling a venture-backed company, including how to recognize when fundraising feedback reveals a deeper strategic challenge.
