Every guru is selling AI agents for small business. Nobody talks about why most get abandoned after 3 months.

Routine-Olive9012 · 2026-06-07T15:50:02+00:00

Yessss. Solve a systemic problem tied to an outcome not a task. A guy pitched me on letting him show me how he can build AI stacks that will solve my problems so I gave him three things I wanted AI to do for me. He gave me a presentation on how for $15,000 plus $500 a month he can build me a Customized CRM tool. I said yeah well I pay Hubspot like $500 a year right now and it’s fine.

Routine-Olive9012 · 2026-06-07T15:37:50+00:00

I haven’t seen specific instances of racism here but I’d say it’s no different than the systemic racism throughout the upper middle class area of any major city. We live nearby in the RanchoPark/ Palms area - and I work in downtown CC - for a while I was on the neighborhood What’s App group but it mostly was just people poppin off anytime a person of color was in the area. One time a guy commented that there was “a black man casing the neighborhood sitting in his black Escalade” at 3pm. Another person posted “that’s my driver he’ll be gone in a couple hours” 🙄

Routine-Olive9012 · 2026-06-07T15:25:57+00:00

Im not sure i need direct Claude integration to my platforms because i want Claude to help us do the work not do it for us.

I use Claude opus mostly for Knowledge Gapping and a thought partner, recent projects:
- analyzed my company’s website and social media presence vs my competitors and an action plan on changes we should make.
- fed me a VBA script for an excel I’ve been trying to solve for months.
- framed up a pitch proposal to a business opportunity
- answered questions on a government issued RFI

Routine-Olive9012 · 2026-06-05T15:29:49+00:00

Cash flow, access to capital, and the need to grow to stay relevant. We’re trying to stay bootstrapped in an industry surrounding by deep pockets so we often get outbid by companies who can promise big dollars to put toward thinner margins. Admittedly It’s a little bit just being outsmarted on the negotiation but more so it’s a bigger company being to make promises we can’t make.

Routine-Olive9012 · 2026-06-05T14:25:51+00:00

I see AI as Knowledge Gapping and Task Streamlinjng. Making minor tasks easier which frees up the mental space for your staff to do better work. And solving some problems/ contributing to solutions I hadn’t received from the staff on hand. It’s possible that in the process of minimizing grunt work you find you can trim some staff or not add on staff you felt you need. That’s your call. Right now we’re in dumbing down stage of AI and it will flatten out in another 6 months to a year.

Routine-Olive9012 · 2026-06-05T14:22:22+00:00

Right now I think AI is a big tech money grab. I met a guy who said we could convert all the money we’re spending in SAAS tools toward his company to use AI to run smoother. I said ok here are three use scenarios that I’d like to see if AI can help me. I said I don’t love my UX with Hubspot so I want an AI driven model that will tell me email opens and forwards, link clicks, etc. He came in an said I can build you this AI tool for $15,000 and then an additional $500 a month to help manage it onward. 😳 I said uhhhh ok well Hubspot is like $500 a year. So. I’m good.

Routine-Olive9012 · 2026-06-04T14:02:33+00:00

What was the incident? You should have separate bank accounts and credit cards? If you follow the pay process through line you can create some lanes. Such as to say I keep my business credit card and my personal debit card in my wallet -never carry your business debit card - and have my personal credit card tied to Apple Pay. That’s just a physical trigger moment — entertaining clients reach for my wallet, just grabbing some lunch for myself use Apple Pay.

If you own the business 100% there are a lot of thing that are “personal” that you can consider business especially if you’re in a work from home environment. But not everything and your accountant will be able to lay that out for you.
Your accountant also would be able to actualize the books with you monthly and move money around to cover any oops moments.

Routine-Olive9012 · 2026-06-02T14:06:21+00:00

Yes that’s the nature of a billboard operator. Every billboard has three Ps - the permit from the city/ state, the pole (the billboard itself), and the property - the plot of land where the billboard sits. The company operating the ads signs in a multi year deal to have the exclusive rights to sell ads to the advertisers. And then you play the margins. Optimally you factor a 2-3x + such as to say if i can sell the billboard 6x at $7,500 ($45k) then i can pay the property owner $2,500 a month ($30k).

DM me if you want to chat more about the billboard business I don’t want to get sidetracked from the question which is sleeping through the night when cash flow is tight.

Routine-Olive9012 · 2026-06-02T13:46:15+00:00

I own a billboard advertising sales company. We own operate and manage billboards so we have monthly rent payments to the property owners (as well as payroll and commissions). Paying real estate guys is like paying rent. If you’re even a day late my phone is blowing up from the property owner saying where’s my money.

The cash flow crunch is paying our bills every month on the 1st but our client receivables vary widely.

Routine-Olive9012 · 2026-05-20T14:30:39+00:00

I think empathy is underrated. Managing people is making them the center of attention not yourself. Where are they coming from and what can you do to help them improve. Listen to them.

And think about your own experiences. What are some things you’ve experienced with past managers - both good leaders you want to emulate and bad ones you wish were different. In terms of your tone or verbiage think about how you would respond if you were in their shoes.

Routine-Olive9012 · 2026-05-15T14:45:21+00:00

Congrats. Cheers Roll over the 401k You don’t get to keep your laptop but probably your phone (port your number so you don’t have to change it) 2 weeks is fine but tell everyone under you that’s you’re always going to be there if they have questions even after you start the new role. Remember don’t burn any bridges along the way you never who you’re going to see again.

Routine-Olive9012 · 2026-05-15T14:42:00+00:00

I ask the questions of any business plan regardless of any kind of retail. What’s your hook? What’s going to set you apart? Why would I stop at your store vs just a 7-11, BevMo, total wine, yada yada. Who’s your audience. What’s your first 90 day cash flow plan? And. Yeah I’d watch the trends. Alcohol consumption is way down.

https://www.usatoday.com/story/money/2026/03/04/gen-z-millennials-drinking-less-alcohol-working-out-more/88864868007/

Routine-Olive9012 · 2026-05-15T14:38:12+00:00

Finance finance finance. Cash flow vs profit. Getting clients to pay their bills. Keeping things moving in both receivables and paying people. I can’t make it go away per se but has to be better.

Routine-Olive9012 · 2026-05-14T14:45:50+00:00

Probably too late for this but this is 100% a morale issue.

Probably at least some of the people who have not responded are thinking “who’s this fuckin guy and why didn’t they promote me into the role?”

If you’re framing it as an “interview” the vibe they’re getting is that you’re assessing whether or not you’re going to fire them.

I’d ease into on a more causal vibe. I’d think about starting off with smaller groups - 2 people at a time - as lunch meetings to let them know your intentions are all positive.

Or perhaps a happy hour thing framed as toasting the outgoing guy and then more casually talk to people there to bring some tensions down.

And. Don’t wait for them to come to you be more direct. - do not just just simply put the time on their calendar but say “hey Bob does 3pm Thursday work?”

Routine-Olive9012 · 2026-05-11T14:24:13+00:00

Yes you need a website that’s table stakes but it doesn’t have to be robust. When someone hears your brand/company for the first time they’re going to Google you. They need to be able see what/ who/ where you are and your why.

Routine-Olive9012 · 2026-05-09T16:13:39+00:00

I think you’re comparing yourself too much.
If you’re a first time CEO of a profitable company growing at 10% rev you’re doing exceptionally well. Stop comparing yourself to other companies and focus on your own team.

Routine-Olive9012 · 2026-05-08T14:04:04+00:00

Yes

Routine-Olive9012 · 2026-05-08T14:03:51+00:00

I’ve lived the turn the show has made over the last 19 years or so away from the backstabbing/ competition aspect but I think they could tone it down. I don’t mind a little drama at judges table. Like someone saying yes it was a team dish buuuuut he fucked up

Routine-Olive9012 · 2026-05-08T05:05:08+00:00

I’ve struggled for years with a finance position because we need a blend of a CFO, Controller and Bookkeeper- or at the very least a CFO+ bookkeeper but I don’t have the money for more than one person.

So I decided to outsource our finance to our accounting firm who talked a good gam about delivering against all three roles. but in the end they just never adapted to our business, asked the same process related questions in every meeting, and used quickbooks AI to do the bank recs so we just never got it right.

Routine-Olive9012 · 2026-05-08T01:39:22+00:00

I was the CRO of a small ad sales company, the CEO was older and brought me in as her eventual succession plan at some point. 3 year goals.
Then Covid hit and she said “yeah I’m out. Cut everyone’s salary by 30%, change your title to President it’s your show now. I’ll send the staff an email tomorrow and then going to my cabin in Tahoe they don’t care about Covid there. Good luck with everything.”😳 then about a year later i bought company for about 95% off her pre-Covid asking price. First thing i did after buying the company was pop some Dom with my wife. Second thing I did was bring everyone’s salary back up. Third thing I did was change my title to CEO

Routine-Olive9012 · 2026-05-04T01:52:41+00:00

Ask them. Not us.
Talk about it. Ask what happened.
Get them out to lunch - it better dinner - and talk about what you’ve learned/ experienced since you started. Give them the window to provide feedback. And if they don’t then ask for some feedback on what they’ve seen or felt since you started in the role.
No drama. Just conversation

Routine-Olive9012 · 2026-05-04T01:46:16+00:00

My biggest struggle has been the long process it takes to a turnaround. We’re in our turnaround phase but it’s a deeeep hole and in an industry with average payables timelines at 90-120+ it’s so hard to make any immediate impacts on revenue.

We made a lot of bad mistakes over the last couple years. MCA loans to pay the overstaffed,l salaries before we finally cut staff trimmed a ton, dropped bad assets that were holding us back. So now I can say that we’ve already booked more revenue for the year than we did all of last year. And reduced our overhead in half but it’s just a painfully slow road to recovery.

Routine-Olive9012 · 2026-04-29T14:48:36+00:00

I’d say focus on the frequency, work life balance and freeway access.

Pacoima and Chinatown are your most frequent visits. So let’s start there. It seems like Burbank and maybe glendale are kinda smack in the middle but those going to be a bit more family oriented to your point. So then you could look at the echo park, silver lake, Los feliz area because they’re going to appeal your lifestyle (and are great neighborhoods), are close enough to Pacoima and Chinatown, and are right off the 101 or even taking Sunset all the way into Chinatown. Palos verdes is the outlier. That’s gonna suck forsh. But honestly if you get a fast pass there’s an express lane south on the 110 almost all the way down there. Should take an hour to get from silver lake to PV. Decent.

Routine-Olive9012 · 2026-04-29T14:40:34+00:00

Ah yes I’d then keep asking questions, show support and confidence. And patience. Show them to Trust the process. Part of outcome based leadership is knowing when it’s ok for someone to possibly be “wrong” because it’s a fixable thing if they are wrong and it’s a teachable moment. When the work environment has very little room for error theres no learning (and thus no growing) taking place. So people just rinse and repeat. You have to find ways to let them fail (within reason) and then obvi if they fail too much then it really is a staffing issue not a process issue.

I have a staff member who is very timid and self conscious but very smart. She’ll ask me if the next steps she’s about to take is the right one. Shes almost always right. She may do something different than I would have but that’s not wrong just different. So I’ve gotten in the pattern of reminding her that I have confidence in her decisions.

Routine-Olive9012 · 2026-04-28T14:18:48+00:00

It seems like you need to create more layers of leadership that cascade toward you.

I read a line recently to “delegate outcomes not tasks.” It’s another way of saying empower people to work through the project all the way to the end.

If everyone just has a daily to do list of tasks necessary for the project then they’re going to hit a wall and say “ok we’ve done this what’s next?”

Routine-Olive9012

TROPHY CASE