Podcast notes – Buying Caitlin Pyle’s Proofread Anywhere for $3M (online course) – Acquiring Minds

Guest: Dom Wells
Host: Will Smith

$3-3.5M annual sales with extremely high margins

Proofread Anywhere – teaches people how to make money online as proofreaders
Female founder was face of the course

One-time fee, various tiers
Community access
Smaller courses as side offers

Buyer didn’t think of it as just a proofreading course, but as one of many ways to “make income online”

$500 course is main offer

How can she charge that much?
-Premium positioning
-Large audience, with existing brand affinity
-Course has a good reputation

Launched in 2014
Founder is Caitlin Pyle
50K people have done it
Backend uses Clickfunnels
Well-known in Clickfunnels community

Buyer was already familiar with her brand

She started as a proofreader herself, teaching her own experience and story

Big risk if buyer takes over a brand whose founder is the face
In this case, Caitlin created all the content, but she wasn’t running the business – already had a professional operator
She wasn’t actively marketing it, either — mostly from Facebook ads
She’d already created 6-12 months of ad creatives
They bought rights to use her image for 2 years after acquisition

Buyer had previously done a similar transaction – had sold his own business and was face of that brand, saw it play out successfully

One way is slowly transition a new face in
Did it with a podcast host before

“Most people don’t care”
New users won’t really know or remember

Plan to hire some of her best students as brand evangelists – already 50K (or 15K?) students
Could be even more powerful story – took the course and now make living as proofreader

Most users’ intro to brand is a free webinar, free workshop – but stepping up immediately to $500 course can be jarring
Want to implement a lower priced ($29) offering

Downside of Udemy – difficult to build sales funnel to really grow students (top classes on Udemy have say 1000 students)
Proofread Anywhere uses Clickfunnels
Buying a course and taking it off Udemy can be risky – but could be potential strategy

Podcast notes – Ujwal Velagapudi (SMB buyer, vending machine biz) – Acquiring Minds podcast

Guest: Ujwal Velagapudi
Podcast: Acquiring Minds

Hometown – suburbs of Detroit (he’s 30-ish)

Bought and sold a dozen cars on CraigsList (CL) while in HS / college
Always made a profit, and learned negotiation and hustling through it

Commercial building for sale on CL – seemed a great deal, 75yo seller owner / occupier
Fire damaged red brick building – 7 Mile in Van Dyke
Was a year out of college
Did entire lease + purchase agreement (PA) himself
Grew this commercial portfolio to 12 units – mixed use, light industrial – at this point was earning ~$5K/mo

Still had day job – supply chain management in aerospace, quit in 2018
But always interested in passive income

Then explored SMBs – pizza, night club – all on CL – spent a lot of time on deals but they all fell through
Finally saw a bar for sale – near Red Wings stadium – rich history, but the arena was being demolished and relocated
Had been bartender in college, even though he didn’t drink
75 seat bar, no kitchen, did some food trucks + temp chefs – $100-200K gross, 1 full-time bartender
Put in LOI, 4 days later had a signed agreement + down payment
Purchasing by himself – knowing it was mostly for his education – “wasn’t for the money”
Hired completely new team eg bartenders – also on CL
Ultimately couldn’t extend the lease, owners wanted him to leave so they could demo the building
Was initially there every day after his 9-5 job – slowed over time
Owned it for 1.5 years, then liquidated everything he could

Also on CL – saw a gym for sale – Snap Fitness, hot gym in area
Personally loved sports, exercise
Bought with cash for $75K – closed deal in 3.5 weeks – was making $50K (so 1.5x multiple), but LA Fitness had just moved in next door
2900 sf, prime downtown location in small Detroit suburb, yoga studio, tanning bed, weight lifting
24/7, keycard
Sold for 2.5x purchase price to his gym manager – had started as a customer, became assistant GM and then GM for him, and eventually bought it over
Always prioritized happiness and efficiency over maximizing profits, outsourced a lot of work, used tech as much as possible (video cams, PoS, DocuSign, etc)
Only spent 10 hours total in that gym – managed it like it didn’t rely on him, relied heavily on financials / reports instead of micro managing

Bought an ecomm business – Amazon FBA selling hats, bags, gloves – negotiated the heck out of it, thought he got a good deal
Offered $180K, $90K down ($500K revenues?) – was a well-known online brokerage
Then he discovered it had a lien, because seller took loan from Amazon which was automatically deducted from earnings
Seller tried to hijack the account, got FBI involved
Seller was a felon with drug issues
Took a big hit, ultimately liquidated it on EmpireFlippers (good experience)

In 2018, multiple income streams, quit full-time job, spent a few months in Thailand, had gone for an entrepreneurship conference
Spent a few months on the beach, 4 hour work week, but “it was so boring”

Increasingly difficult to find good M&A deals on Craigslist – back then there was a lot of misclassified deals, 80 year old sellers
Now brokers are picking off everything, sellers more sophisticated, marketplaces more fragmented (eg, FB marketplace)

After ecomm, purchased minority ownership in consulting business for niche insurance software
Moved to Texas for it, 20 year old company, was acquired by Oracle
Had monopoly in a very niche business as systems integrator
But covid hit and really hurt business
Oracle refused to sell it back to him
Wasn’t able to compete with new startups

HiByron
MicroAcquire – saw a promising target, LOI in a few days, closed sale in 5-6 days
Acquired for 5-figures, $2.6K in MRR, US-based virtual assistants + tooling (geared toward online business
owners), $44K in trailing 12 mo revenue
Like a staffing agency + tech platform
Lot of R&D gone into it, great base, he was excited to own business
Great seller transition – SOP, tutorials – seller was focused on a new project

**Likes to close very quick, helps him w/ sellers“I’m a cash ready buyer that will close within 2 emails” – has standard set of questions, very attractive to sellers

Living in Mexico now

Let someone take over HiByron (the VA biz) – 60/40 split for any new revenues (“phantom equity”) + 1 year vesting
Has grown considerably with new management
From $2.6K MRR to $45K MRR – specifically one big new customer (a vendor to OnlyFans)

Latest acquisition: Vending business
Talked to a lot of brokers, shared requirements, looked in Mexico & Canada too
Looking for $multi-million deal
3 targets:
1. Chemical distribution (60 yo biz) – lost to strategic acquirer
2. Tech biz (phone systems securitization) – lost to PE / group of investors
3. Vending biz – jukebox, arcade games, ATMs – bars, restaurants – “seemed super weird to me”

Reviewed financials – very stable business – 7-figure cashflow, 50/50 split, labor is biggest OpEx
6 month process to close – all his previous M&A experience really helped, sought financing from 100+ banks and lenders, dealt with a lot of rejection
Main issue: Entirely local – had to be around his base, maybe at most a 2-3 hour radius
End consumer is B2C, but direct customers are B2B (eg, restaurant or theater)
80-90% shutdown during covid

Vending biz primer
Owns and places equipment
Sends own collector + technician for operations
Two critical elements – 1) service + 2) customers
Service – If jukebox goes down at 11pm, you must take care of it asap; if broken, order parts and replace in 1-2 days
Customers – gotta baby ‘em, one of few vendors that actually PAYS the customer – mutually beneficial, perfect alignment
Don’t wanna be 1+ hours away from customers
In vending, LOTS of one-man shows, small route that they do everything for, biz plateaus
A few are vending aggregators – buy multiple routes
Lots of vending sellers came to him after he bought the first one
Bought 3 more since that first purchase
His operation is biggest in the state, but doesn’t compare to national operators
Cash-flow is now multiple 7-figures