10 early mistakes Entrepreneurs and Founders make And how to avoid them

Khushi Bhatia

founder mistakes, startup mistakes, common startup errors, early stage founders, startup survival, founder advice, startup funding mistakes, investor relations startup, founder mental health, entrepreneurship lessons

A candid founder-to-founder note attributed to Fittr CEO Jitendra Chouksey is circulating with a message that cuts through the usual startup hype: building a business is not just about raising capital or “looking confident”, it’s about staying in the game long enough to win, while protecting your health and your family.

In the post, Chouksey lays out ten common mistakes founders make early on, and the practical mindset shifts he believes can prevent them. The themes are consistent and unsentimental: guard ownership, don’t outsource your judgment to investors, optimise for survival, and don’t let the business consume the rest of your life.

Below is a structured breakdown of the points as shared, along with what they signal for founders navigating the first, most fragile years of a company.

1) Over-diluting too early for capital

The first is direct: Do not dilate too much for early capital. The blog also provides a distinction that first-time founders often overlook: your company can succeed, but your personal outcome is not guaranteed if you have given too much equity too early.

Avoid it by:

Treating early dilution like a one-way door decision.
Raising only what you can justify with clear use-of-funds and milestones.
Remembering that “successful company” and “successful founder” are not automatically the same thing.

2) Misreading how money shapes confidence and power

The post argues that money “works differently”, that people can appear more confident in rooms not necessarily because they’re more capable, but because they have financial backing. It frames money as something that can buy confidence, though not the deeper anchors like love or family.

Avoid it by:

Not confusing someone’s financial position with their competence.
Grounding yourself in what money can’t buy, especially relationships and support systems.
Avoiding “status intimidation” when negotiating or pitching.

3) Feeling guilty about meeting your needs while serving investors

A key point: founders shouldn’t feel guilty for taking care of their own needs alongside investor outcomes, especially if investors are already receiving strong returns. The post suggests that if you don’t have uncomfortable conversations, others may assume you’re doing fine even if you aren’t and adds a tough line many founders recognise: don’t expect investors to care about you personally.

Avoid it by:

Having explicit conversations about founder salary and sustainability early.
Normalising the idea that founder stability protects the business.
Separating “investor return” from “founder wellbeing” as two legitimate discussions.

4) Turning to investors for business advice instead of customers

Another clear warning: don’t treat investors as your operators. The post urges founders to educate themselves and not rely on investors to manage or grow the business, stating that investors bet on the founder to figure it out, not to run the company for them. The recommended alternative is equally clear: talk to customers as much as you can.

Avoid it by:

Using investors for introductions, hiring help, and accountability—but not as the primary decision engine.
Building a tight feedback loop with customers and user behaviour.
Developing your own operating rhythm and decision-making discipline.

5) Trying too hard to please everyone and fearing “burning bridges”

The post takes a contrarian stance on a common founder anxiety: don’t worry too much about burning bridges, because the world is big and you don’t need everyone on your side. It warns against losing your soul trying to please everyone and offers a personal metric instead: make your “yester self” proud.

Avoid it by:

Being selective about relationships and partnerships.
Prioritising clarity over people-pleasing.
Measuring progress against your own growth, not constant external approval.

6) Ignoring physical, mental, and social wellbeing while chasing financial outcomes

“Catching up” is one of the most applicable parts, connecting well-being to performance. According to the passage, “If you prioritize only your financial well-being and not pay attention to your physical, mental, or social well-being, trust me, it catches up.” There are simple, actionable tips to follow: train for 30 to 45 minutes, do not consume “garbage” food, and do not spend time around people whose behaviors negatively affect personal performance, as “the people around you are the ones that help shape you.”

Avoid it by:

Scheduling exercise like a non-negotiable meeting.
Treating diet and sleep as “founder infrastructure,” not optional lifestyle choices.
Choosing peer circles that reinforce discipline and perspective.

7) Playing safe instead of training for fear

The post is asking founders to be fearless and to expect the worst and train every day to prepare for it. Reading it, it seems like a reminder to founders that the worst case may change, but it never goes away.

Avoid it by:

Naming your fears clearly (market failure, team conflict, cash crunch, rejection).
Building routines that increase tolerance for discomfort (hard conversations, disciplined execution).
Practising action under uncertainty rather than waiting for perfect clarity.

8) Expecting the journey to be mostly “good times”

A rare line for startup advice: embrace that everything is transient, and that building a business includes good, bad, and horrible phases and that “mostly it’ll be bad and horrible.” The point is not pessimism; it’s expectation management.

Avoid it by:

Replacing “I should feel great” with “I should keep moving.”
Building emotional resilience as a skill, not a personality trait.
Using difficult phases to strengthen systems rather than questioning your identity.

9) Treating survival as success and saving for rainy days

The post reframes success in a long timeframe: surviving = success. The message is to optimise for survival, and if things are going well, save for rainy days, because there will be many.

Avoid it by:

Conservatively managing cash and burn.
Building buffers even when revenue or momentum spikes.
Making decisions that reduce fragility rather than maximise short-term vanity metrics.

10) Putting family first, always

The closing line is the clearest value statement in the entire post: “Family comes first! Always!” It lands as a deliberate counterweight to the culture that glorifies sacrificing everything for the company.

Avoid it by:

Defining “non-negotiables” with family early (time, presence, boundaries).
Recognising that isolation and broken relationships don’t count as success.
Treating family stability as part of long-term founder durability.

Resonance Of Founder Mistakes

Without hyperbole or industry speak, this blog post is like a reality check for entrepreneurs at the start of this journey, particularly those who find themselves in an ecosystem of fundraising indicators, social media bravado, and being seen as “ahead” of everyone else.

At its core, the message is that founders should: