u/Flaky-Taste2253

My friend uses Gmail with a custom domain for work and mostly send regular 1:1 emails to clients. He had already taken care of the usual email setup steps and most of their emails are just proposals, follow ups, or normal client conversations.

Still every now and then, the emails landed in the spam folder. Could it be the domain reputation issue or is Gmail just stricter with spam filtering lately?

I use Neo Mail and already have its email backup enabled but I had still feel better keeping a 2nd local backup just in case. I have tried OfflineIMAP when I was using Gmail, but I found the setup confusing. I scheduled regular backups and opened them in Thunderbird whenever I needed to read old emails.

Is there a self hosted tool that can back up my full mailbox, including attachments and let me browse it offline?

I run a small advisory(travel) business, and I get emails asking for prices before we have talked through the trip.

Part of me wants to reply with the pricing straight away but I am worried they will judge it without knowing what’s included. Asking for a call sometimes feels like I am dodging the question.

How do you usually handle this?

One thing I have been struggling with as a solo travel advisor is finding the right balance.

My repeat clients take up most of my time between planning trips, making changes and answering questions. I love that they keep coming back but it also means I barely have time to market myself or bring in new clients.

Then when things slow down, I realize I haven’t done much to fill the pipeline. I want to know how do you balance keeping existing clients happy whole still growing your client base? What’s worked for you folks?

My sister needs a professional email setup so when we researched, we kept seeing SMEs and startup owners complain about google workspace for things like pricing, setup issues and same old stuff.. but in most cases, they did not switch.

Why is that?
From my end, I suggested her a few other email providers but she thinks that because moving business email is too risky to newer options, she wants to stay with google workspace only.

I do not feel this is the right logic but the ones who stayed on Workspace, was it really the right choice or was it more about not wanting to deal with the change?

Meta rolls out another paid feature for Insta and WhatsApp and most people just shrug and move on.
But if I tell a customer there’s a small fee for a custom request or charge extra for a last minute itinerary suddenly I have to justify each dollar.

It feels like big companies can raise prices, add subscriptions and lick features behind paywalls without much pushback. Small businesses do the same thing and we’re expected to apologize for it.

I get that nobody like paying more. I don’t either. I just find it interesting how differently customers react depending on who’s asking for the money.

Does anyone else feel this way or am I looking at it wrong way?

I plan custom trips for clients and just spent 20 minutes scrolling a whatsapp thread to find someone’s airport transfer time because I could not remember which of the 5 versions we agreed on.

Most clients want everything on whatsapp since it is quick and personal, but itineraries never stop changing & every edit is another message buried in a thread that is already weeks long, always making it one endless scroll.

The part that scares me is missing something that actually matters, like if a transfer time changes, things get lost in the chat and a client ends up stuck outside airport at 6am. That's on me.

Email feels like it would fix half of this with real threads and a record of what we agreed, but clients prefer whatsapp and I do not want to make it harder for them just to make my life easier.

So what do you all use: email or whatsapp? Has anyone gotten whatsapp to work for this, or do you just give up and move everything to email?

I run a small travel advisory business and my customer base is mostly families, couples and busy professionals who want customized trips without handling all the planning themselves. So most of then prefer quick WhatsApp communication over long email threads.

As an individual handling chats, once there are 25+ active chats it gets messy fast.

I came across the launch of whatsapp plus / updated whatsapp version and I am really interested to know if it can help my business scale and also sending itineraries & managing client chats easier?

A few weeks ago I got burned pretty badly. I spent hours planning a trip for a couple. They loved it… then ghosted me and booked the same itinerary somewhere else. So I finally added a $75 planning fee, applied toward the booking if they move forward. Now I’ve got a new problem.

Before the fee, I was getting at least 8-10 inquiries a month. Since adding it, I’ve had 6 people reach out and 4 vanished the second I mentioned the fee.

One person literally said, “ Wait, I thought travel agents were free lol.” I get that nobody loves upfront fees, but I also can’t keep building custom trips for free just so people can price shop me.

For other service business owners: how do you charge for the planning/ strategy part without killing the conversation right away?

I love exploring new tools so my first instinct was to build a clean stack when my brother asked me to help manage his domain email setup. On the other hand, I also think that it is a waste to pay for full workspace in the start from where he stands.

He is planning to keep costs reasonable and obviously wants to avoid rebuilding the whole email setup 6 months later. So what’s the best pick?

Business email provider/selfhosted plus shared inbox tools plus CRM add-ons.. which stack works the best?

He is open to experiment so any advice would mean a lot.

So someone commented in this community that you should never keep the domain and web hosting with the same hosting with the same provider and I want to know why.

Also, was the user right about this?
Is this a golden rule or it depending on the provider and use case?

Recently I spent almost 3-4 hours planning a Europe trip for a couple. I found cheaper flights, mapped out their routes, recommended hotels based on walkability, even fixed their itinerary because they originally had them changing cities every single day.

They kept saying stuff like wow this exactly why we wanted a travel advisor. And then two days later they ghosted me. Last week I randomly saw the girl tagged in instagram stories on the exact same trip… same hotels, same schedule, same everything. They just booked ut somewhere cheaper after I did all the planning.

And honestly, I think this is my own fault. I made the process too easy because I thought being extra helpful would build trust faster.

Now I’m debating whether I should start charging a small planning fee or only share basic itineraries until someone is serious.

Would love to hear any advice or boundaries that have worked for you?

As someone who works in travel planning, I have noticed way more people adding “reddit” at the end of their Google searches lately.

like instead of searching:
“best hotels in Cancun”

they’ll search for:
“best hotels in Cancun reddit”

Same thing with airlines, hidden fees, airport safety, all-inclusive resorts, train passes in Europe, etc..

Honestly, I kinda get it. A lot of travel blogs now feel super sponsored or seo-written, while reddit usually gives you the real experience from actual travellers. Sometimes messy, but real.

But I’m curious from the traveler side, are you guys trusting Reddit more than travel websites now? And if you are, what makes something feel trustworthy vs fake or recycled online?

I was randomly scrolling and came across Proton business ecosystem. Now all I knew about proton was its email service but this new setup looks pretty cool.
In a way I see this, this is nothing but a polished version of google workspace with better privacy settings. I have not seen many people talk about using it but as someone who loves trying new tools, this caught my eye. Now I am not someone who is looking to switch email providers, I just want to know how useful this new Proton ecosystem is and what new features it offers.

Is anyone here using Proton for their entire business setup?

I am very curious to know if proton is trying to become another google workspace alternative or is it mainly Proton Mail with some extra apps attached only?

I would love to hear your thoughts on this!

For me, it was: more outreach emails equals to more results.

I used to send 500 cold emails every day, but got no responses, whereas one good outreach email changed everything for someone else.

This got me to think that we have all started out by following the rulebook for ‘how to’ and ‘what are’ the best email practices for business emails. But I feel that the longer you deal with business emails, the more you realize that some of that advice is outdated, overly simplistic, or just wrong for certain businesses or startups.

What business email rule did you once follow but no longer trust? And what replaced it for you?

I run a growing travel agency and honestly most AI tools have created more headaches than business growth for me. I started using Claude for itineraries and client emails, GoHighLevel for automation, and an AI chatbot for lead capture because everyone said these tools help you scale faster.

Reality has been very different.

Claude writes polished stuff that often makes no sense operationally. The chatbot gives robotic replies that kill conversations. GoHighLevel automations constantly need checking so I do not send weird follow ups to real customers.

I am trying to grow the business properly, not spend all day fixing software mistakes. Has anyone else dealt with this? What should I actually be focusing on at this stage?