There is a phase in every founder’s journey that no one really names. It does not come at the idea stage, when everything is fragile and unproven, nor does it arrive once the business is large enough to have departments, agencies and layers of decision-making.
It sits uncomfortably in between. The product works, the mission is real, people are listening, expectations are rising and yet, when you look at your video content — the thing that’s meant to represent you — something feels off. It is not wrong enough to justify ripping everything up but it is not good enough to feel confident sharing widely. This is the awkward stage.
Many founders experience this and it shows up in hesitations, second-guessing and half-finished content plans. It also shows up when you delay publishing, or cringe slightly when revisiting a video you were once proud of. It is more common than you think.
When “Good Enough” Stops Being Good Enough
Early on, scrappiness is a virtue. DIY videos, smartphone footage, rough edits and improvised messaging feel authentic. They signal hustle, speed and experimentation. Investors and early customers often forgive rough edges because they’re buying potential, not polish.
Businesses evolve faster than founders expect, however. Suddenly, the audience shifts. You are no longer speaking only to early adopters who enjoy discovering things before they are finished. You are speaking to people who need reassurance. People who are making decisions that carry financial, reputational or personal risk. At this point, video stops being “nice to have” content and becomes evidence.
Video becomes evidence of clarity, seriousness and that you understand your audience as well as your product. This is where many founders first feel tension with their own content. The video isn’t bad but it no longer reflects who you are now.
The Subtle Pressure Video Carries
Video carries a disproportionate amount of meaning. A single founder video can influence whether someone believes in your leadership. A short explainer can determine whether your product feels simple or complicated. A campaign clip can shape whether your organisation feels credible or chaotic.
Unlike text, video doesn’t allow much abstraction. Tone, pacing, framing and confidence all leak through whether you intend them to or not. Video reveals uncertainty as easily as it communicates certainty.
Founders feel this instinctively. They may not articulate it in marketing language, but they feel the weight of it. That’s why the awkward stage often manifests as avoidance rather than action. Publishing feels riskier than staying silent. So, they stall.
The Three Common (And Understandable) Responses
When founders hit this stage, most respond in one of three ways.
1. Doubling down on DIY
The logic is seductive: “We’ve come this far doing it ourselves. We just need to get better at it.” So, they upgrade cameras. Learn new software. Spend evenings tweaking edits. Try templates, AI tools and shortcuts. The output improves technically, but something still feels misaligned.
The problem is distance. Founders are too close to the business to see the story clearly, and too busy to maintain the consistency video demands.
2. Jumping too early to agencies
Others swing the opposite direction. They assume the discomfort means they have “outgrown” DIY and need agency-level production. So, they commission polished films, impressive visuals and expensive deliverables. The result often looks beautiful but feels strangely hollow.
Agencies, especially at scale, are built to deliver outputs, not proximity. They can make things look impressive, but they rarely sit close enough to the founder’s thinking to evolve with the business in real time. The video looks right but doesn’t feel right.
3. Avoiding video altogether
The third response is complete withdrawal. Founders stop publishing. They tell themselves video is not a priority right now. They will come back to it after the next milestone, funding round or product release. The silence however creates its own cost. In fast-moving ecosystems, absence is interpreted as stagnation. The story continues, just without you shaping it.
None of these responses are foolish. They’re rational attempts to manage uncertainty but they all miss the real issue.
The Real Problem Isn’t Production
The real problem is narrative alignment. Your business has moved into a new chapter, but your video story has not caught up. The language, framing and emphasis that worked earlier no longer match the decisions your audience is making now.
Video becomes awkward when it’s answering yesterday’s questions. When founders think, “This doesn’t quite represent us anymore.” That instinct is correct.
What Video Needs to Do at This Stage
At the awkward stage, video has a different job. It is about confidence transfer and no longer about visibility alone. Your audience, whether they are investors, hires, partners or customers, are asking these questions:
- Do these people understand what they’re doing?
- Can I trust them with my time, money or reputation?
- Do they think clearly under pressure?
- Are they aligned internally?
Good video doesn’t answer these questions explicitly but implicitly, through coherence, tone and restraint. That requires something more subtle than polish. It requires clarity.
The Missing Middle Path
What most founders do not realise is that there is a middle path between DIY chaos and agency distance. A way of working with video that stays close to the founder, evolves with the business and remains strategically grounded, without becoming bloated or disconnected.
This middle path focuses on:
- story before spectacle,
- process before perfection, and
- continuity before campaigns.
Instead of asking, “What video should we make?”, it asks, “What do people need to understand about us right now?”
So, producing one-off hero pieces is sidelined for building a narrative spine that everything else can attach to. Instead of outsourcing thinking, it supports it.
Why This Stage Feels So Uncomfortable
The awkward stage feels uncomfortable because it coincides with identity shift. Founders are no longer just builders. They are becoming leaders, representatives and decision-makers at scale. Their words carry more weight. Their presence signals more than they intend and video becomes a mirror. Mirrors are confronting when you are in transition.
Many founders mistake this discomfort for inadequacy and assume they are failing at marketing, or that they’re “not good on camera,” or that others have some secret they’ve missed. In reality, they are simply outgrowing their first narrative.
Reframing the Problem
Instead of asking, “Why isn’t our video working?”
A better question is, “What has changed in our audience’s expectations?”
Instead of asking, “How do we look more professional?”
Ask, “What would make someone trust us faster?”
Instead of asking, “What should we post next?”
Ask, “What decision are we trying to make easier?”
This reframing removes pressure. It shifts video from performance to service.
What to Do Instead
If you recognise yourself in this stage, the solution is not to stop using video. It is to slow it down. To step back from outputs and return to intent.
That means:
- clarifying the story you are actually telling now, not the one you started with,
- identifying the moments where video genuinely reduces friction for your audience,
- building a repeatable, sustainable approach rather than chasing formats, and
- staying close to the founder voice, while refining it with perspective.
Video at this stage should feel like a conversation that’s becoming clearer, not louder.
A Final Thought
If your video feels awkward right now, it is a growth signal. It means your business has moved beyond improvisation but has not yet found its next rhythm. It means you are taking your audience seriously. It means you care about alignment and not just attention. That tension is uncomfortable, but it is also where the most meaningful work begins.
Your business has outgrown its first draft. The next version doesn’t need to be perfect. It just needs to be honest, clear and intentional.
