Barrett O'Neill Profile picture
Mar 10, 2022 16 tweets 3 min read Read on X
What got you $500K won't get you $5M.

The evolution of a bootstrapper:

Master these 5 roles to scale your startup:
Growing from concept to millions requires adaptability -- in mindset & skillset.

Especially from the founder, who needs to shift his/her daily responsibilities with growth.

Casey Clark from Cultivate Advisors created this roadmap for bootstrappers: ⬇️ ⬇️ ⬇️
1. Hustler

In the early days, with no money or network, founders need to do everything.

Flush with passion, the challenge at this stage is knowing how to channel energy into results.

To graduate from the hustle phase, spend 70% of your time on sales.
Reading too many (or the wrong) business books encourages founders to focus on the wrong things.

You don't need systems to scale or perfect OKRs (yet) -- you need sales.

Become a master of selling & set the foundation for growth.
2. Experimenter

You've proven that this idea has legs. Now how can you optimize your offering and your processes?

-A/B test your offer
-Add employees & vendors to fulfill tasks not in line with your strengths
-Find ways to lower customer acquisition costs before scaling
Begin building processes to produce repeatable results.

Establish KPIs/ OKRs so that a quick snapshot can give insights into the health of your business.

Check out this tweet for tactics to lower CAC:

3. Visionary

Ready for scale, founders need to delegate.

Many bootstrappers get stuck in this phase because it's uncomfortable relinquishing control.

It's difficult to shake the desire to "protect" what we've built.

It usually unfolds like this...
Founders (falsely) believe no one can perform as well as they can.

Reluctantly, they make a hire. Quickly, they can't imagine how they lived without that team member.

Learn about delegation from a management expert:

Like many before me, I've found delegating to be the hardest phase.

It requires putting your ego aside and empowering others to perform.

I've found that with a singular focus, the person appointed to a task ends up being more effective.
4. Systemizer

With a fully functioning team, you need to add management to replace yourself.

It's challenging because it's expensive, risky & will remove you from the day to day.

But it's essential to pave the way toward giving the company what it needs:
A CEO focused on strategic initiatives to guide the company forward.

This phase includes letting others control budgets, make hiring decisions, and design processes (without your input).

On the other side of systemizing is the opportunity to scale for years to come.
5. Influencer

You've built a product with demand, attracted talent & built systems.

Amplify everything by becoming a respected voice in your industry.

Use social media to build a following. The earned authority and trust will attract customers and talent.
Also, position yourself to be a keynote speaker at industry events.

Being an influencer gives you the inside track on acquisitions & opportunities for growth that others will miss out on.

This has been a driving force behind my recent Twitter growth.
Self-awareness is key:

Which phase are you at, and what does your business need you to be at this moment?

If these aren't aligned, you need to evolve -- no matter how uncomfortable it may be.
Sources:

These 5 stages of bootstrapping resonated with me as I have been/ am going through them.

Check out his work here:

greyjournal.net/work/work-busi…
If you found this helpful...

Follow me @barrettjoneill for more content on business & growth.

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More from @barrettjoneill

Mar 22, 2023
95% of websites will dramatically improve SEO by adding more content and backlinks.

Use this trick in Google Search Console to find keywords your site already ranks for.

You'll rank in the top 3 positions MUCH faster by creating blogs and videos around topics/keywords Google… twitter.com/i/web/status/1…
The snippet you can copy to recreate the search:

(?i)^(who|what|when|where|why|is)

Query --> custom --> paste snippet --> apply
Also for weekly content about SEO and building high-cash flow machines join 9,200+ who read Business with Barrett:

barrett-oneill.beehiiv.com/subscribe
Read 4 tweets
Mar 16, 2023
I'm a 31 year old millennial.

Our parents' generation taught us to trade time for money.

Here are 4 ways to use leverage to get wealthy without working 24/7:
Millennials and their parents view the world differently.

Mainly because during our childhood/their prime working years (80s - 2000s) the world experienced rapid tech innovation.

The internet created financial opportunities that seemed foreign to our parents. Image
In 2019 tech entrepreneur Naval Ravikant recorded a podcast about leverage.

He says there are 4 ways to increase output beyond our own effort:

1. Labor
2. Capital
3. Code (Technology)
4. Media (Audience)

While reflecting on his ideas, something hit me…
Read 17 tweets
Mar 8, 2023
Imagine you're 99 years old on your deathbed...

Will you regret how you're using your time today?

5 sure-fire tactics to owning your time:
Everyone can relate to this:

We want to be a great parent/spouse, earn lots of money, have a social life, and be in shape.

We're told there will be tradeoffs - we can't have it all.

But we can have more than we think if we control our time.
SCHEDULE OPTIMIZATION

I got this trick from Kayak Founder Paul English ($1.8B exit to Priceline in 2012).

Paul says (and I agree) that happiness is a function of balance.

Try a color-coded calendar to quickly identify priorities and time breakdowns.
Read 14 tweets
Feb 18, 2023
The most important skill your teachers never taught you.

Negotiation.

7 simple strategies to become an elite negotiator:
ANCHORING:

Is a psychological tactic that uses "shock value" of a VERY high/low offer.

It creates a desired reference point for the subsequent (real) offer.

When the real offer is presented, it's compared to the anchor YOU set -- and appears like a bargain.
Had an anchor not been set, the REAL offer wouldn't seem as attractive as it does.

EX:

Submitting an offer on a property for 25% below the asking price. Then providing a reasonable "concession" at 5% below the ask.

It creates perceived value for the seller.
Read 18 tweets
Feb 6, 2023
Since May 2022, it's been a challenge to grow organic traffic for many sites.

I recently ran an experiment and grew traffic by 44% in two months.

Try this plan for a struggling site:
First some brief context...

There has been issues with site indexing and many substantial drops in traffic since May.

Nobody can be 100% certain as to why, but when in doubt, choose quality over everything else.

To deliver quality is Googles' mission.
The case study company is a service business that's been around since 2014.

They had 157 posts, many were outdated, no longer relevant, or low quality.

Posts like this used to rank more easily, but now high ranking posts need to provide more value.

Here's what we did:
Read 11 tweets
Jan 30, 2023
99% of business owners peacock top-line revenue growth.

But if your goal is to stack cash you need to focus on gross profit.

Here's why it's important and what the shift did for me:
Gross profit is the amount of cash available for allocation to operations AFTER you've paid product/service costs.

Costs of goods sold (COGS) include:

- Raw materials
- Sales/leasing
- Manufacturing
- Storage/freight
- Labor

It's the "real revenue" you run a business with
If sales are growing, but gross profit is stagnant/declining, you have one of these problems:

1. Pricing is too low
2. Product costs are too high
3. Service/product dev. is inefficient

For healthy companies, more revenue should make the gross profit per unit higher.
Read 12 tweets

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