Kenny Pitman

Here’s the reality.
The next group is moving forward with the 6-week Rise Up Rent to Rent challenge.

This isn’t a taste test.
You get the full structure to start properly.
all for Less than the full Mentoring course.

No fluff.
No guessing.
Just the step-by-step process that gets results.

Do nothing?
You’ll still be watching other people make their first deals, wondering why you didn’t start when you had the chance.

If you’re done thinking and ready to move, Then get on and buy your ticket now - 16 spaces left, we start in 18days

kennypitman.com/6weekchallenge

5 hours ago | [YT] | 0

Kenny Pitman

Stop waiting. My student just hit £11k in 10 days.

One booking added £815.50.

While they act, most are stuck overthinking, stalling, losing months and money.

Next year, nothing changes if you don’t.

Structure. Pressure. Accountability. One step at a time.

Cash flow first.

Support when it’s uncomfortable.

10 hours ago | [YT] | 0

Kenny Pitman

You think rent to rent is about property.
It isn’t.
It’s about time.
And most of you have none.
You work all week.
You check your phone on Sundays.
You tell yourself it’s “just busy right now”.
It’s been busy for years.
You already know the steps.
Find the deal.
Secure the landlord.
Set it up properly.
Then stop touching it.
But you don’t.
You overthink.
You delay.
You wait until it feels safe.
Meanwhile another year goes.
Same job.
Same stress.
Same “I’ll start soon”.
The people doing rent to rent aren’t smarter.
They just accepted short-term pressure
to buy long-term free time.
Structure.
One strategy.
Cash flow first.
Accountability when you want to disappear.
That’s it.

16 hours ago | [YT] | 0

Kenny Pitman

Jak Woodliff just did £850 for 2 nights.
This is not luck
It’s execution, Focus and Accountability.
Doing the uncomfortable things that everyone else stalls on.
Alot of people say this...., “I’ll start next week.” and then before you know it, months slip by.
Confidence fades. Opportunities disappear. Next year, nothing changes. new year new me, and the loop continues
Jak’s showing exactly what happens when you stop hesitating.
One strategy at a time.
Cash flow first.
Support when it’s uncomfortable.
Results follow.
This is what happens when you stop doing this alone.

1 day ago | [YT] | 0

Kenny Pitman

I took on a one-bed flat that barely broke even. On paper, it looked like a dead deal.

But I solved a real problem for a landlord with a portfolio. I delivered, stayed professional, and built trust.

That “loss” became a stepping stone to many rent to rent deals. One deal turned into multiple. More properties. More profit.

The lesson? relationships matter (especially with the right people) more than winning everytime. One uncomfortable decision today can set you up for many wins. Just make sure you can ride the wave

Skip the Carousel

1 2 3 4

2 days ago | [YT] | 0

Kenny Pitman

This property went live…


and the first booking covered Christmas and New Year.
10 nights.
£1,800 plus.


And the review came back exceptional across the board.
Not in peak summer.
Not in a booming market.
Right at the start of winter.


That did not happen by accident.


Before this ever went live, I was clear on three things:


1. Who this property was for-
Not everyone.
This was built for large families and multi family groups.
Nine beds.
Lots of Space.
Plenty Comfortable
A hot tub to lean into the luxury stay angle.


2. Market data before emotion
I did not guess. This was not a stab in the dark
I checked the demand.
I checked booking behaviour.
I checked what actually performs in this area, not what looks good on the day of looking


3. Calendar and pricing set up properly from day one
No panic discounting.
No random selection of pricing.
Built for longer stays and premium guests.


That is why the first booking was not luck.
It was market positioning.
Most people rush to list a property.
Very few take the time to design the outcome first.


And that is the difference between hoping for bookings
and controlling them.


If you want to learn how to set this up properly,
from due diligence to listing to calendar strategy,
comment TRAINING
and I will send you access to my full free training on rent to rent strategies

Skip the Carousel

1 2 3

3 days ago | [YT] | 3

Kenny Pitman

Saw Emily post earlier and it genuinely made me stop for a minute.
She’s talking about handing her notice in.
Not in a dramatic, fed up way.
In a calm, grounded, we’ve actually built something way.
Four properties in.
VAT registered.
Paying herself the same wage she used to get from a job.
Running a six figure business and still saying they chose to leave money in to grow it properly instead of rushing to take it out.
That’s maturity.
That’s patience.
That’s real business.
The bit that got me most wasn’t even the numbers.
It was when she said they now get more time to do what they want instead of what they have to.
That’s the whole point.
Not Lambos.
Not flexing.
Just choice.
Honestly so proud of them.
Because I know what it took to get there and it was not glamorous.
Just showing up, doing the work, and not quitting when it would’ve been easier to.
And if you’re reading this thinking you’re miles behind because you’re only on one or two deals…
So were they.
So was everyone.
This is what progress actually looks like.

4 days ago | [YT] | 0

Kenny Pitman

🚀 OK, something exciting for you guys!

For the first time EVER, you can get involved for less than £500 👇

My team said I’m insane for doing this... but whatever.
We’re opening The Rise Up 6-Week Property Challenge —
and it’s limited to 25 people only.

Once it’s full, doors close.

🔥 Here’s what you get:

✅ One private group of 25 people
✅ One live Zoom call each week with me
✅ Full training course covering HMO, SA, and Deal Sourcing
✅ Every resource my mentees get - contracts, calculators, scripts, D2V templates, compliance checklists, flow charts... the lot

❗ Note: This does not include private 1:1 support - all help and feedback happens inside the group so everyone benefits.

💡 Who this is for:

People who’ve been wanting to start but don’t know where to begin

Those who want to “try it out” before joining full mentorship

Action takers - not excuse makers

❌ Who this is NOT for:

Anyone expecting me to do it for them

People looking for overnight success or hand-holding

🗓 When we start:

As soon as all 25 spaces are filled, or in 3 weeks’ time - whichever comes first.

Don’t wait - these spots will go insanely fast.

👉 Click here to join now → buy.stripe.com/eVq4gAddZ3bi6kd713dQQ0v

3 months ago | [YT] | 2

Kenny Pitman

🚀📞 From phone calls to financial freedom…

This is Dan Benstead

The start of this year he was just starting out, since then he's:

• Made hundreds of calls to agents and landlords.

• Pushed through the frustration of deals falling through.

• Stayed consistent when others would have quit.

And the results speak for themselves ⬇️


✅ 2 HMOs already up and running — fully occupied.
✅ Just collected the keys to his 3rd property.
✅ Another 2 deals in the pipeline right now.

The momentum is real. In Dan’s own words -

once those next two go through, he’s seriously considering leaving his job.

This is what happens when you stay relentless. One deal at a time turns into options, freedom, and a whole new future.

Dan, we’re buzzing for you brother 👊 The Rise Up community is behind you all the way.


Comment 'START' below

and i'll send you the HMO blueprint to help you get started

Skip the Carousel

1 2 3

3 months ago | [YT] | 6

Kenny Pitman

We had 2 mentees collect HMO keys over the weekend

Louise collected her first property.

Dan collected his third HMO

We don’t just teach you to get your first property

We help you scale past £5K/month

Skip the Carousel

1 2

3 months ago | [YT] | 5