Persistence, Preparation, and Alignment: What Actually Moves a Fundraise Forward, myTrudy Client Spotlight

Fundraising is not just about having a good company. It’s about being able to explain it clearly, defend it under pressure, and follow through when the answer is no.

This month’s Lion Lookout looks at how deals get evaluated and what matters most when there is still limited data, and how to find the right partners on your growth journey.

We sat down with Adam Eisenberg of Ibex Ventures to give founders an unfiltered look into how venture investors actually evaluate opportunities, what diligence looks like behind the scenes, and how early decisions actually get made.

A lot of what Adam shared mirrors what we see across our own client work, especially how often strong companies stall because their story or targeting is misaligned.

Over the conversation, one theme came up repeatedly:

At the early stage, uncertainty is the norm. This makes the founder, the story, and the way it is communicated far more important than most realize.

1. Prepare Your Materials, Even If They Will Change

Early-stage founders often push back on projections, business plans, and models because they know they’ll pivot and the numbers won’t be perfect.

The point is not precision.

The point is discipline.

Putting projections together forces founders to ground their thinking, define assumptions, and create a roadmap for what they are trying to build.

Even when those assumptions change, the exercise sharpens the story and gives investors a framework for how the founder thinks.

Well-prepared materials also make diligence smoother.

When founders show up prepared, they are easier to underwrite.

2. When You Need Funding, and Investors Need Traction, Target Your Funds Carefully

It’s a classic case of the chicken and the egg.

Investors often want to see traction in order to get an injection of capital, but founders say they need capital just to get traction in the first place.

What to do?

Adam’s answer was simple.

It depends on the investor and it depends on the stage.

Funds like Ibex often act as an early check, and invest as early as just two co-founders with an idea. Others want a more defined product, a clearer business plan, or revenue.

Problems arise when founders pitch all investors as if they are the same.

Many fundraising challenges are really alignment problems.

Raising early requires speaking to investors who are built for early-stage companies.

3. Be Relentless

No matter how strong your company is, fundraising inherently involves rejection.

That’s why founders who stop at ‘no’ risk missing out on ‘yes’ later on.

Adam’s advice to founders preparing to reach out to Ibex was straightforward:

Prepare as much as you can. Put the information together concisely. Then be relentless.

If a VC says no, follow up with real progress. Ask why they passed, learn from the feedback, then return later with better data.

Persistence works—but only when it’s paired with substance.

Interested in working with LionRun?

4. When ‘No’ Becomes ‘Yes’

A firm passes. The founder follows up. Six months later, they come back.

The firm passes again.

The founder returns once more with meaningful progress and points out what the investor missed the first and second time.

Then the firm makes the investment.

Sometimes investors cannot see the vision as early as the founder can. That does not always mean the idea is wrong. It can be a matter of timing or information.

Founders who follow up with substance give investors the chance to change their minds.

That’s how ‘no’ becomes ‘yes.’

Client Spotlight: myTrudy

We sat down with Avi Steinlauf, the CEO of myTrudy, a personality-driven career platform that empowers job seekers to understand their potential and match to roles where they are most likely to succeed and thrive, not just qualify on paper.

Avi noted that myTrudy already had most, if not all, of the right information, but they lacked the impartiality to organize it and tell that story clearly.

Working with LionRun, Avi said, they were able to select the most important points and pull the story together “in a way that would have been difficult for us by ourselves."

It was a great example of how clarity, not more information, is often what moves a process forward.

When asked what he would tell another founder in a similar situation, Avi stated:

"I would recommend the folks at LionRun without reservations." 

It was an honor to work with the myTrudy team, and we can't wait to see all that they accomplish next!

To learn more about myTrudy, connect with Avi on LinkedIn.

P.S. Email replies are on! If there are any topics you'd like to explore or questions you have, feel free to reply to this email.

Until next time, we’ll be on the lookout!

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P.S. Email replies are on! If there are any topics you'd like to explore or questions you have, feel free to reply to this email.

Until next time, we’ll be on the lookout!

Interested in working with LionRun?