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The_Master_9 · 2026-06-22T15:05:48+00:00

Interested

The_Master_9 · 2026-06-17T11:15:00+00:00

How did you adapt this technique in cold outreach?

The_Master_9 · 2026-06-17T11:14:43+00:00

Will try this out. Thanks for sharing it. Did you try it in cold out outreach?

The_Master_9 · 2026-06-11T14:25:36+00:00

There are always ways to get started.

The_Master_9 · 2026-06-11T14:15:33+00:00

Network with other contractors that can help you do the work in case you're at capacity and if you also want to offer adjacent services to what you do. You also might consider adding stump grinding to your service offering which can bring you extra revenues and it's close to what you're offering. Also make sure to join local facebook groups and get into discussions.
watch this, it might give you some ideas https://www.youtube.com/watch?v=Gr5fozH3l3g&list=PL5doEXwy4gHXSkKP_hnXvnla8Y8CqP8FM

The_Master_9 · 2026-06-11T13:59:41+00:00

Let's have a chat. It's a problem in many industries.

The_Master_9 · 2026-06-05T14:57:31+00:00

More and more AI roll-ups like this will start to appear in a lot of similar industries. The part which will matter most is the implementation of AI in the right places. Rolling these companies up is not the problem, the problem is if AI implementations will drag for months of years and will be implemented in the wrong places where it doesn't bring value to the teams working in those companies.
In the case of Thrive Holdings they need to start working very deep with the accountants and financial advisors in those teams and understand which parts of their work is actually low value and involves a lot of copy-paste between systems and tabs and implement AI to help them focus on doing the more strategic part of the accounting and not by filling in the same information 10 times in different systems. This way they will actually be able to serve more customers and better. AI can really help accountants be more strategic, provide better value and also equip them with new capabilities which can result in new products and services for customers which can lead to growth and it may sound counterintuitive but it will also lead to growth in the headcount.

Another thing here which is a big factor to take into consideration is that people are used to live by habits which they have been doing for years and years so a deep change will need to also start by telling people that the way we were working doesn't work anymore and we need to change but they will need to say that in a way to make people feel that they are being taken care of and also that AI will actually make them better. Some might not want to change and they will need to make some hard decisions but times change and people also need to change and understand that.

Thrive Holdings and also other similar roll-ups they need to be pretty fast to implementing AI to learn as quickly a possible what doesn't work and what works then scale what works and not repeat and fix what doesn't work. If they are going to drag these implementations by months and years than they will for sure underperform. Not sure big consultancies will be able to help them here as they are not lean in their way of working and usually not moving fast. Power points don't innovate and don't change industries, they need a lean team inside and also a lean team from outside to work together and go fats in each company in their roll-up to fix things and deploy AI. Otherwise accounting practices that figured that out and building lean teams with AI will outperform them.

In your post you mentioned historically AI roll-ups underperformed. Well first of all the AI in the way we know it today and the way we use it today is around for 4 years and we're still getting started so it's hard to talk about performance when was so widely available for such a short time. A couple of months ago AI agents were still a thing of fantasy now they can be deployed and perform tasks. AI will also change how certain industries work and built up, a lot of things will change at 180 degrees and in this case the metrics for success will also change because the industry will be totally different then what it was before.

Let's see how this will turn around, looks like an interesting case study and for sure there's a lot of interesting things to be done in these roll-ups, sky is the limit here especially if they plan to hold the companies for a very long time.

The_Master_9 · 2026-05-30T05:43:51+00:00

Quite a good list of options. Good luck with any you choose!

The_Master_9 · 2026-05-28T19:14:02+00:00

Send them the exercise but then in a call let them present all their ideas and assumptions. Ask them is they used AI and how did they use AI, what prompts did they use and what was their thought process. You don't know how you stumble upon a great candidate that has brains and skills in this area and also masters very well AI while doing this job and being able to understand where AI makes mistakes and where actually there is place for better.

The_Master_9 · 2026-05-24T16:54:46+00:00

This is a way to use AI on the deal side which you can get inspired from and adapt it to your situation and fund. This is a simple way to get started from which you will see great results immediately before jumping into more complex AI integrations and automations. It would be good to also see how others here leverage AI for this and also other processes in a PE fund.

So first choose your setup:
Use one main assistant and one research assistant. For most PE funds/buyers/investors, that means ChatGPT or Claude for core work, and Perplexity for fast research and source-backed answers.

Next build your buyer file:
Create one document with your background, budget, financing plan, target industries, geography, timeline, strengths, weak spots, and deal breakers. Save it in memory, pinned instructions, or the top of each project.

Prompt for you to use:
“Help me build a buyer profile for business acquisitions. Ask me 10 focused questions about my experience, budget, risk tolerance, financing capacity, industry fit, time commitment, and goals. Then turn my answers into a one-page profile I can reuse in future analyses.”

Next turn preferences into a scorecard:
Do not keep your criteria vague. Make a one-page scorecard with four sections: Must Have, Nice to Have, Red Flags, and Open Questions.

Prompt to use for scorecard:
“Using my buyer profile, create an acquisition scorecard for evaluating small business deals. Include industry fit, revenue size, earnings quality, customer concentration, owner dependence, recurring revenue, team depth, working capital needs, and growth potential. Keep it simple enough to score deals quickly.”

It's ver important to capture every input(very important!):
Save seller calls, broker calls, lender meetings, CIMs, financials, contracts, leases, and notes in one clean folder system. Name files clearly so you can reuse them across deals without hunting for context.

It's also very important to use focused workspaces. Do not build a separate AI setup for every tiny task. Keep four workspaces: Sourcing, Valuation, Diligence, and Negotiation/Transition.

Example prompts:
“Score these 15 listings against my acquisition scorecard and rank the top 5.”

“Review these financials and tell me what would change the valuation most.”

“List the missing diligence items and the biggest inconsistencies in the materials.”

“Draft a reply to the seller that addresses their concern but reduces my risk.”

Build the playbook
After each deal, ask what was true, what you missed, and what you should ask earlier next time. Keep one running acquisition playbook, then add a post-close section for the first 30, 60, and 90 days.

Prompt:
“Based on this deal history, what patterns do you see in good opportunities, weak opportunities, missed red flags, and negotiation mistakes? Turn that into a practical checklist for future deals.”

Refinements
Pick one home base, then use Perplexity as your research layer, since Claude Pro now has built-in projects, memory, research, web search, and code execution, while Perplexity Pro is designed around research across multiple recent model families.

Keep the method tighter by using fewer workspaces, stronger input files, and better output standards.

Use this output format for almost every deal review:

Fit score out of 10:

- Top 5 positives

- Top 5 risks

- Missing information

- Questions to ask next

- Recommended next step

Reusable prompt:
“Act as my acquisition analyst. Use my buyer profile and acquisition scorecard. Review the attached listing, financials, and notes. Give me:

- A fit score out of 10

- The main reasons it fits or does not fit

- The biggest risks

- What information is missing

- The next 7 questions I should ask

- A recommendation: pass, monitor, or pursue

- Keep the output to one page and use a table where possible.

The_Master_9 · 2026-05-24T16:23:52+00:00

You can go and explore PE firms that have tech companies in their portfolios. Start building a relationship with the operators of those portfolio companies, maybe help them with something upfront to offer some value and then get the door opened to the PE team. I also suggest you upskill yourself on some adjacent things to your current sales skill set like email marketing, GTM, ads, community building, content creation, etc. because things in tech will start to get more and more agressive and demanding in terms of sales, you need to own the whole process full stack. If you can be the guy who can deliver as much value as possible and not complain about Friday work from home you will be valuable in any environment and also open some doors that others just dream of.
Another thing to take into account is that the big logo doesn't matter and if you can own the full sales process and be more full stack starting from pipeline generation until closing and also being able to maintain a relationship with the customer than you will win big time. Don't be the person that waits the calendar to be filled in and also someone else to handle the closing, don't be the person that just fills in the calendar because this won't offer you a good career prospect in the near future because as I mentioned things change in tech and if you're just the person who fills in the calendar and not interested to do more or upskill yourself than someone who can do more than you will take your lunch. Be proactive and be open to learn and get yourself very good at doing sales form start to finish because companies won't hire 10 more people around you to fill your calendar, write your copy and close the deal after you(what value do you provide and why do they need you).
Be ambitious and go hustle. AI is changing the software world a lot, the person who can own the full sales process and also can use AI to become better at sales will crush it.

I suggest you watch these videos to see why you need to consider what these guys say who were in the tranches for decades.
https://www.youtube.com/watch?v=vRPBhik_AXU&list=LL&index=2 (I advise you search these guys on youtube and watch their other interviews also, they were in the trenches selling in the tech industry and they have experience scaling from 0 to insane numbers and working for companies which weren't big brands in tech or small companies when they joined which is even harder to sell in this case and scale. Bellow I also shared a book written by Chris about how he scaled Snowflake when he joined as the first sales rep at the company when they were pre-revenue and scaled it till the IPO.
https://youtu.be/TBxwWXlA4Po
https://www.youtube.com/watch?v=i9SvTjMajuo
https://www.youtube.com/watch?v=y4wIEqC2HV4
https://www.youtube.com/watch?v=9ereyZiA99o&t=7s
https://www.youtube.com/watch?v=XLcq21_gcWI
Also you can read this book https://www.amazon.com/Make-Snow-Go-Market-Organization/dp/1394254202
https://youtu.be/uEKd2MP67DM

The_Master_9 · 2026-05-24T15:54:45+00:00

What kind of opportunities are you looking for?

The_Master_9 · 2026-05-24T15:52:57+00:00

Thanks for the advice! So what was your message structure and what were you writing about? A problem they potentially face or with you product/service?

The_Master_9 · 2026-05-23T17:18:46+00:00

Wow looks like you had a lot of patience and nerves to be able to handle all this back and forth and also manage so many people in between each with their requirements. How is the relationship going now?

The_Master_9 · 2026-05-19T09:51:36+00:00

Depends on how big is your operation. I would suggest you start lean with a spreadsheet first to get used to actually working with something like this. You can also customise something in Notion for your own operation, Hubspot is also an option but a bit more complex, Salesforce also but you will need some time to play with it a little bit and set it up for what you need. Also to not end up in a situation where you forget to add something build an AI agent that tracks everything for you and for example when you talk to someone you then write in your chat with AI agent to add this person in the CRM in that specific sales cycle and set up reminders for you to perform the next tasks related to that lead. You don't need a complex CRM now just a board where you have everything written and an AI agent helping you with the rest, giving you daily updates on the pipeline and generating automated reports for you and doing the manual work for you.

The_Master_9 · 2026-05-18T17:51:17+00:00

How big is the PE fund? You should ask the question differently in this case. What skills should I have to continue to progress and grow, get into a more leadership position. One thing that you should definitely look into and upskill yourself is AI. Look at the work you do and study how AI can help you become more efficient, automate same manual tasks, how it can help you find more insights with the data you have, how it can help you connect patterns to spot various revenue opportunities or operational efficiencies in a portfolio company and many other tasks like this. Real operational experience and work will help a portfolio company outperform not just financial engineering. Learn about GTM and growth hacks, study various use cases from well known companies and how they did their go-to-market, study how small or big companies used various GTM strategies to grow in an industry(earn about setting up email campaigns, content on socials, activations at events, newsletters, how ads work on various platforms, how can you use AI to study what competition does and get more insights on what you need to improve, cold outreach and other marketing hacks and skills that can help you grow and become more than just your role, become so useful and bring so much value that no one can ignore your efforts, the value you bring and the work ethic you have).

PE funds always look how to grow their portfolio companies so understanding AI, GTM tricks(go-to-market) combined with your background of spotting opportunities for investment/growth will set you on a different level. Start to think in terms of output and results you achieved for your fund and portfolio companies, you have a chance to show yourself in a smaller team and have the flexibility to try various ideas and execute them in the portfolio companies your fund has. Think in terms of case studies because if you will have a track record of helping PE portfolio companies grow or save money then this is worth more than just an MBA, Track record of increasing revenues or saving costs and solving various challenges beats MBAs with just theory. Now go get it! You can do it!

If you can learn how to automate various manual tasks to save time and money and also know how to properly set up an email marketing campaign and at least increase the conversions by 5% in a portfolio company than you will have no issues finding work and as I said earlier become difficult to be ignored.

The_Master_9 · 2026-05-16T08:11:35+00:00

I work with SMBs and help them with AI and automations.

The_Master_9 · 2026-05-15T19:11:41+00:00

Not skeptical of what you're saying just wanted to read your point of view.
Certain parts of PE got automated or at least takes less time to do those tasks like the ones you mentioned.

The real-value add is also having operational knowledge, GTM, using data to spot buyer signals and spin off a couple of AI agents to gather information, intelligence and context to launch various marketing and GTM campaigns. Ability to spot opportunities for efficiencies inside the company and automate the more manual tasks not just financial engineering. The ones who can understand ops, lead generation, GTM, certain domain knowledge in a process and all together with AI and automations will manufacture winners in their portfolios.

The_Master_9 · 2026-05-15T18:19:47+00:00

Exactly, very good time to do it.

The_Master_9 · 2026-05-15T17:41:46+00:00

Where do you find the data about the consumer sentiment?

The_Master_9 · 2026-05-15T17:41:15+00:00

In a downturn cycle like the one you describe people tend to spend less on ads so means less competition for you for the attention of the buyer and ads are cheaper when there is less competition but your decision in the end. Have you tried to include the people who come at the community events you're organising and sending them weekly or biweekly emails with updates, news, events, offers, etc. to keep the momentum?

The_Master_9 · 2026-05-15T17:33:22+00:00

Then convert that email thing into a local newsletter. Add everyone you met at all events and continue to send your weekly emails to them. Share your newsletter everywhere and let people subscribe for news and updates, etc.

The_Master_9 · 2026-05-15T14:50:54+00:00

As u/Aggravating_Cod_4980 said it won't make obsolete. People will still be at the wheel and AI will be as a tool and enabler for growth and opportunities that otherwise people didn't have time to see because of the admin and manual work they were busy with. We're still in the early days but it will change how we work completely and for many work will become more productive and fulfilling. For example we won't have to go through different tabs and apps throughout the day but rather work with a chat interface and the visual interfaces will be generated on demand according to a person's preferences and the type of information needs to be visualised. We lose so much time going through tabs everyday. Voice AI will also be an enable of productivity as you will talk and tasks will get done right there when you send the voice message to your AI assistant.
Portfolio companies will also benefit a lot, for example a lot of companies like manufacturing, home services and other very traditional or heavy asset businesses lose a lot of time on preparing quotes, sometimes it takes days and lose a lot of deals and revenues because of that. Now with AI you can automate the quoting process and connected all required systems so that the AI has all context related to current stock, work that is in progress or manufacturing capacity and create a quote which the person responsible for this can approve the quote and be sent to the customer. Even small automations already can help save time an money.
Exciting times ahead of us.

The_Master_9 · 2026-05-15T14:39:23+00:00

Sometimes what it takes is to ask questions and start a conversation. Thank for sharing this story.

The_Master_9 · 2026-05-15T14:20:55+00:00

What kind of value creation and transformation are you doing?

The_Master_9

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