I'm an early-stage founder selling software to manufacturing companies in India, and I'm handling sales myself.

One thing I'm finding frustrating is the chain of approvals at some companies. Getting someone interested is one thing. Figuring out who can actually approve the purchase, and how to get there, is another.

For founders who've been through this, looking back at the deals you closed:

• What did those buyers have in common that the ones who kept delaying didn't?
• How early did you figure out who controlled the budget and who else needed to approve?
• What actually moved things forward when a deal got stuck internally?

I'm also curious where you draw the line between being patient with a company's process and spending too much time on something that isn't going anywhere.

Would love to hear about a specific deal: what you were selling, how long it took, and what finally got it signed.

Best resources to figure out who's getting funded, what pivots they are making, what VCs are looking for, in the Bay area? How can I get daily updates like that. Unfortunately, I can't move to the bay area, unless I get into YC which doesn't seem to be happening rn. I want to see the trends of what those startups are following

I’ve been working on my startup for a while. I built a prototype, but nobody uses it regularly (I know that’s a signal). When I talk to friends and coworkers, they recognize the problem, but they’re not interested in a tool, it doesn’t seem painful enough. I’ve had the same conversations on LinkedIn: people complain about it, then keep living with it.

The problem I’m focused on: people need to deliver work but don’t understand the company’s context, what something is for, how the business works, and how systems connect.

At this point I’m stuck: keep pushing on this, or drop it and focus on something else?

Grad civil engineer in Sydney, been building something on the side and I've hit a wall.

Quick context on what it is: construction teams lose lessons between projects constantly. A job gets burned by something, learns it, and 18 months later a different team at the same company makes the identical mistake because nobody talks across projects. Every contractor has a "lessons learned register" and every one of them is a spreadsheet nobody opens. I've built a tool that captures lessons in about 30 seconds (voice or text, AI structures it) and surfaces them when someone hits a related problem, instead of waiting for them to go searching.

The problem validation has been genuinely good. Posted about the problem on some construction subs and got 20+ practitioners agreeing, including a bloke with 25 years across tier 1s who said he's never seen a lessons system work anywhere. Had a few calls with directors and senior engineers. Everyone agrees the problem is real and expensive.

Where I'm stuck: nobody wants to be the first to actually trial it. I've got a working prototype, I've offered it free, one director even volunteered to be a guinea pig unprompted. But there's a gap between "yeah that's a real problem" and "yes I'll run this on my team for a month." Everyone's busy, nobody wants to be first, and a grad with a side project is competing with their actual job for attention.

So the questions:

How did you get your first pilot or first customer over the line? Especially anyone selling into a conservative industry where nobody wants to go first.

Working at a startup with a 409a valuation that keeps going up a bit each year raising the FMV the employee common equity modestly.

Option strike price when I started was $1 then FMV a year later was $1.50 and a year later $2.05 and so on. All makes sense.

Problem is software company (SaaS) valuations have absolutely plummeted and are now being sold for 2-4 x ARR (vs 10-15 x ARR in the before times) which puts the company at a fraction of the common stock implied FMV valuation.

I spoke with company financial people and they say the 409a is based on 3-year average growth rates and 10-15x sales multiple but:

1. the current year growth is much lower than 2 years ago
2. 10-15 sales multiple is way way higher than what SaaS companies are being acquired for now

Can 409 a valuations be dramatically mis-priced like this?

In this case, the 409a suggests the company to be worth almost 10 times a reasonable ARR multiple in today's market using comparable company sales/acquisitions

Just curious on this front. What would you say is the minimum capital a startup should have before it considers hiring a few people?

Guessing it's not really ethical to hire people unless you know you can pay them for at least 6-12 months, unless of course they're aware of that and willing to accept that level of risk...

What should I do

This weekend I've realized I've been that entrepreneurship person that's a wantrepreneur for 10 years, without making a single cent.

The most I can name of being paid in an entrepreneurial way was helping 1-2 people in college move with the help of my pickup truck.

I've been involved in startups for as long as I can remember. I got a scholarship to a high school startup incubator back in the day, worked on an app that didn't take off. Then worked with a startup, kind of the third person after the two founders, that was geared around COVID that also kind of dropped.

In college, I did a lot of things that could have turned into businesses but then didn't. For example, I worked as a personal trainer, almost got certified but didn't. But that could have taken off. My degree was in industrial and systems engineering.

Then after college, I got a day job. Somehow it was in electrical aerospace engineering, but mostly related to requirements, certification, and wire installation. Modeling how wiring and wire bundles are installed on the aircraft. It was only two years, and looking back, I learned a ton, but not, in the grand scheme of things, that is necessarily transferable out of that company, which is part of the reason I left it to join a smaller company, which is where I'm at now.

While doing that day job, I started another startup that I kept working through but wasn't passionate about. It was something that I was going to work on with my mom, because of her expertise in textiles but she ended up being 10% involved because of a crisis she had during the time. anyway the market cap there was too small. dying industry. It was a niche outdoor gear product in a very small market, with not that high demand. I dissolved that business during R&D a few months ago because I kept saying that I wouldn't leave my corporate job until that business launched. But because of the factory timelines, it would have been until this upcoming January at the earliest to actually even launch it. So there was no good way to sell it and see if there was interest without buring through the rest of my savings on a first production run.

Then over this past May/June, I tried to do AI automations for small businesses and consulted a lot of businesses about doing that for them. I was living in Philadelphia at the time, didn't get any responses. I did some networking with people in my network about it, but no one really took me up on a job.

I got really close to a job for a good amount of money. It would have been in automation for a specific person. I got close, he was interested, even sent him the contract, but then he didn't follow through. That would have been a very difficult technical challenge for me in general, but I would have figured out the development and software aspect of it. Anyway, I never was really good at selling, but that was the closest I came. I wish I worked on it a bit better, but then I also thought, okay, if he's not interested, why push? Am open to counters here

That was from a program I had joined. It was only a couple thousand dollars and I was able to afford it. That was about AI automation, really teaching it. It was valuable. I probably shouldn't have paid for it in retrospect, but whatever.

I've been considering doing things such as joining a different accelerator for acquisition entrepreneurship or getting more into that because no one in my life does it, and it's very daunting to do when you don't have people to do it with. I've been trying to find communities that do it here in NYC. Everyone says join a meetup, but the demographic of what you're going to find depends on where you're at.

I've been going to a lot of networking events in New York, and they've all been very tech-heavy. No one even really has my engineering background. It's a lot of tech and finance, which is new to me. But I've been hanging out with some people in startups, and I'm definitely very impressed. Also meeting more women (i'm a woman lol) that I met in my previous neck of engineering.

I'm trying a new run this weekend where I reached out to about 30 people on LinkedIn and some on Reddit regarding doing customer discovery for people who are busy, as another test of trying to actually provide value and actually do the one part of entrepreneurship that makes money.

Anyway, please don't be too harsh. I've done the best I could given my circumstances, given no mentors that have seen me through all this time. I've had short-term mentors through some nonprofits and stuff like that, but very short-term, and they kind of made it clear that when I wasn't actively working on a business, they could no longer meet with me.

I really have not had any family, any friends, or anyone who has seen me through in terms of business/engineering all these years. My family grew up under communism with no concept of business/capitalism still to this day, at least for my mom. I'm not in contact with my dad for diff reasons. It's had to be very self-directed, and I didn't really know when I was doing the wrong thing.

When I was in the thick of my last startup, I spent a lot of time messing around with the details that really I should have gone through faster. How should the website be? What potential partnerships would I have? My mentor at the time had me really think about partnerships where, with my personality, I couldn't really imagine myself doing partnerships with retail shops and other kinds of lessons so that people could wear my garment while they do it. But that was the activity, and that was what I spent time on.

I spent a lot of time figuring out the international supply chain and hiring a contractor in the UK to help me design and develop it. I even spent time writing legal contracts for the factories that I was working with and researching the factories. I even considered setting up my own factory in florida as that would've been faster.

I did learn a lot, but I didn't know enough about business to do that. That first startup incubator that I did, not really talk to us about venture funding. They really kind of drilled bootstrapping down into our heads, and I wish in a way they hadn't because I only learned about how VC funding actually works and sort of what private equity and syndications are, honestly, a week ago.

And I only learned about startup funding rounds because I'm in NYC and was at an event with young startup founders, and they were mentioning their Series A, and then a lot of people in New York were talking about it, so I looked it up. But it took all these years and a decent amount of intelligence otherwise to even learn what these terms actually mean.

A lot of the struggle is that I've had a lot of ideas and not really been sure where to go. I'm ambitious and I know I could really do whatever I set my mind to. Right now I'm really trying to set my mind to the right thing.

Right now I've been considering real estate deals. I have a friend who's a real estate developer with a well proven track record of hundreds of projects at this point, so if I do a rental or flip with him, that's an option. I've been researching some other real estate ideas, thinking about coaching or doing the kind of services for other founders in New York that are either at a nine-to-five, or maybe something to help other founders just to get my foot off the ground. Thinking of engineering consulting, but not sure about what. SaaS is overdone, and then eventually doing the whole acquisition thesis.

But for now, really just trying to figure things out and learning about real estate deals, and I've been evaluating the real estate deals with that sort of acquaintance of mine. But I can't say he's really a mentor, though. It's more of a friend, and I don't think we get super detail-oriented about that stuff.

My current day job that I just started is still in training, and it is training for stuff such as being an energy auditor. But all of my training is from the internet because the owner of the company I'm at has just been really weird with all of his employees and does not disclose anything.

I've just been, I was supposed to be doing sales for them, with energy and real estate, but I've really not been exposed to any of the projects. Nothing. I've asked him about it.

I have been applying, and I might actually start another job in a few weeks, which will be a sales job. I've never done sales, but I figured that clearly I suck at it, so it's something I need to try after all this time. I've been applying to those kinds of jobs just to kind of make money to bootstrap my failed half startups lol.

But really my biggest thing is I have not really made actual money while doing all this entrepreneurial stuff. It's really just been satisfying different needs of wanting to have a project of my own or just interests and learning.

And now I really wanted to get honest with myself and ask for advice on specific things for me to do. Please don't make it generic.

Based on my background and this pattern, if you were me, what would you focus on for the next 6–12 months to actually make money and build real business skills? Would you focus on selling a service, doing a real estate deal, pursuing acquisition entrepreneurship, or something else? What would you stop doing?

Really appreciate y'all in advance for reading this. Thanks so much

Been offered to join a new startup that has raised about 300M so far. Id be one of their first technical hires to run their whole R&D department (which doesnt yet exist and I will have to build). They offered me a nice base salary for the region and 0.25% equity post raise with a supposed valuation of 1B.

Initially I will have to be doing a lot more development than research to get the first plant off the ground, but hopefully after an initial push to build the structures of the company I can focus more on the cool part.

I am wondering if this amount of equity is common or should I be asking for more? I will ask for more eother way, but if they dont give it to me I wanna know if its a good deal for the amount of effort.

So this happened recently and it's got me Thinking a bit.

A friend of mine, freelancer with 4+ years experience, got approached by my employer. Wanted to bring him on retainer, monthly, for two of his businesses one being the agency I work at (where I'm the lead designer).

Dude grinded hard

• Made a whole month's worth of content super fast
• Everything got approved, no complaints

Then payday comes and my employer just goes:

"Your contribution to the agency was nothing, I'm not paying you for that."

Which is straight up not true. He ended up only getting half the payment and quit the next month.

Now I'm sitting here thinking... can he pull the same move on me?

• I'm the one who built and maintains the whole AI-powered content pipeline that lets him serve his clients in the first place
• I also do all the branding work, most of the time with barely any brief, and still deliver stuff that looks premium and put together

It will be really hard for him to replace me because the work I put in will at least take 6 months for someone else to match, both in effort and in the amount of thinking that goes into it.

I know this might not be the case with every agency founder out there, but stuff like this really messes with your reputation and the quality of work you get in this industry.

Honestly just trying to figure out my next move here. Anyone dealt with something like this before? What would you do?

I once received advice that selling a 500-1k $ per month B2B product (even if proven with demand and PMF) harder than selling a 1000$+ per month service

And to this day I’m not sure if that’s true or false because I keep cycling between either turning what we do into a product or a service (it’s in B2B sales and lead generation, which could be a product at that price, or a service)

Would love to hear your advice if you understand both models and which makes the most sense and if that advice is true or false

Does anybody have any general advice towards running a dessert bar?

How much should I typically invest to start out, and what are the main challenges owners typically face.

is it customer acquisition and retaining them?
Or the rising costs for materials?
Or other issue and risks?

Any and all advice is greatly appreciated!

I have a company that operates in financial services. It is an antiquated sector so the impact of modern AI tooling is quite profound. I kept it simple on the surface because of the prospective users.

This causes a few issues:

The onboarding - Everyone is asleep at the wheel in the old gentlemen's club comfort zone which surprisingly isn't an entry barrier because it up-ends the status quo but because the training and transition component of it is cumbersome, going to potentially get expensive and require ongoing support (AI or otherwise).

No regulation - The way everything is done would give compliment to a snail so I have adopted the don't ask for permission, maybe consider asking for forgiveness if the concerns raised are reasonable and not to preserve their ivory towers. Legal may become an irritation in a year(s) time.

Scope - Adoption can or will be national immediately so the geography for the aforementioned onboarding and "Old school face to face" prospects raises the overhead with travel.

All of this is liberally accounted for in the licensing fees and I could absolutely grow this slowly on my own if it didn't have such a fragile and potentially short edge/shelf life. Even with the patent work, at the end of the day, the engine and corpus is code and will eventually be reverse engineered given the impact this has, what I can charge for it and still be way under the existing costs to manage the work flow it obliterates. It is literally weeks into 5 minutes and a team into a guy sitting on the can flipping back and forth between Angry Birds and the platform.

I don't have the capital to explode this nationally to secure the dominant seat before the competition comes out of the wood work and I have been exhausting the typical mechanisms for capital which often take months anyways to get finished IF it is approved. I don't have the luxury of time.

I need a participating investment partner. Capital is half of it, I need someone who is functionally able to help take this to market. It is finished, branded, hosted and currently in use in full production.

Where can I go to begin having this conversation? Don't say dragons den.

I have a company that operates in financial services. It is an antiquated sector so the impact of modern AI tooling is quite profound. I kept it simple on the surface because of the prospective users.

This causes a few issues:

The onboarding - Everyone is asleep at the wheel in the old gentlemen's club comfort zone which surprisingly isn't an entry barrier because it up-ends the status quo but because the training and transition component of it is cumbersome, going to potentially get expensive and require ongoing support (AI or otherwise).

No regulation - The way everything is done would give compliment to a snail so I have adopted the don't ask for permission, maybe consider asking for forgiveness if the concerns raised are reasonable and not to preserve their ivory towers. Legal may become an irritation in a year(s) time.

Scope - Adoption can or will be national immediately so the geography for the aforementioned onboarding and "Old school face to face" prospects raises the overhead with travel.

All of this is liberally accounted for in the licensing fees and I could absolutely grow this slowly on my own if it didn't have such a fragile and potentially short edge/shelf life. Even with the patent work, at the end of the day, the engine and corpus is code and will eventually be reverse engineered given the impact this has, what I can charge for it and still be way under the existing costs to manage the work flow it obliterates. It is literally weeks into 5 minutes and a team into a guy sitting on the can flipping back and forth between Angry Birds and the platform.

I don't have the capital to explode this nationally to secure the dominant seat before the competition comes out of the wood work and I have been exhausting the typical mechanisms for capital which often take months anyways to get finished IF it is approved. I don't have the luxury of time.

I need a participating investment partner. Capital is half of it, I need someone who is functionally able to help take this to market. It is finished, branded, hosted and currently in use in full production.

Where can I go to begin having this conversation?

I'm a solo founder building a B2B SaaS for a specific type of independent professional. It's live and the core works, but it's early and a big part of the roadmap isn't built yet.

I'm stuck on one question: charge from day one, or let the first users in for free?

My case for charging: free users don't tell me whether anyone would actually pay, and free-beta feedback tends to be polite rather than honest. Paying is the only real signal.

My case against: asking for money for an unfinished product feels wrong, and it might scare off the exact early users I need.

For context on price: cheap tools in the space run about $10-80/mo, and the enterprise versions sold to firms run a few thousand per user per year. My product sits in between. My plan is $199/mo list and $99/mo for the first few customers in exchange for regular feedback.

For those who've been through their first 10 customers:

1. Did you charge before the product was finished? Looking back, was that the right call?
   
2. If you started free, did those users convert when you turned on pricing?
   
3. If you gave founding customers a discount, was it for life or time-limited? Which one would you do again?

I have a marketplace startup for Trading Card Games that I have built and is solid in terms of its function. I've just recently started marketing, and have just a few real users.

I feel that my crux at the moment is getting some good listings to fill out the site and make it look legit for new users.

I was thinking of reaching out to vendors on Instagram and offering some sort of deal, like $25 if you list 5 cards on my site. Looking for advice on how to best reach out to people, or more generally fill out listings.

Hey everyone!

I'm currently evaluating a possible pivot for my startup, Jacko.

We've been building an AI-powered personal finance product, but I'm exploring whether the same technology could be more valuable for early-stage startups and founders.

The idea is an AI finance agent that helps founders understand their startup's financial health without constantly maintaining spreadsheets.

It could help track:
- Cash position
- Revenue and expenses
- Burn rate
- Runway
- Recurring expenses
- Weekly financial insights

I'm not building this yet. I'm trying to validate whether this is actually a painful problem before investing time in an MVP.

If you're a founder, I'd really appreciate your feedback:

- How do you currently track your startup's finances?
- Do you regularly track burn and runway?
- What's the most frustrating part of managing your finances?
- Would an AI tool that automated this be useful for you?
- Would you pay for something like this?

I'm especially interested in honest criticism and reasons why you wouldn't use something like this.

Thanks!

Hi everyone, I’m part of a cybersecurity startup offering penetration testing and managed security services.

We’ve worked with Vision Australia, and we’re now trying to figure out how to consistently find more international clients. Having previous client work is helpful, but we need a repeatable way to get in front of the right buyers and turn those conversations into paid engagements.

We’re considering targeted LinkedIn outreach, partnerships with IT providers and development agencies, and sharing technical case studies in relevant communities.

For founders who have grown a B2B services business:

• Which channel brought you your first consistent flow of qualified prospects?
• Did focusing on one industry or one specific service improve your results?
• How did you use previous client work to build trust with new buyers?
• Would you prioritize direct outreach or referral partnerships at this stage?

I’d appreciate specific experiences, including approaches that took a lot of effort but didn’t lead to clients. If you were starting again, what would you focus on for the next 30 days?

I’m 24 and pretty early in my career and I’m honestly not sure what I should be optimizing for right now. I’d really appreciate advice from people who are older and have more experience in tech.
I graduated from a great university with a physics degree and started my career at a very small startup. I was one of three engineers and had a ton of ownership. I was doing ML/LLM work, data engineering, research, and just generally got to work on a lot of different things. The company was very early stage and there were only a handful of people, so I was around the same people basically all the time.
The thing is, I actually really liked the work. I was working 7 days a week at times, but the work itself wasn’t what made me miserable. I liked building things and I felt like I was learning really quickly. I was surrounded by people who were much smarter than me technically, which I thought was what I wanted.
But I also constantly felt like I was the dumbest person on the team.
I would go into meetings and feel like I had nothing useful to contribute. Sometimes I would say something and realize afterward that I hadn’t explained myself very well. I would then spend a lot of time thinking about whether everyone thought I was incompetent. I started taking normal gaps in my knowledge and normal mistakes as evidence that I didn’t belong there.
The CTO was also very intelligent but could be pretty condescending. There were times where I felt like I couldn’t ask a question without feeling stupid. Another engineer eventually left, and some of the reasons were related to the same general environment.
There was also a pretty significant rupture with a coworker I had become extremely close with. We had spent a huge amount of time together, both personally and professionally, and that relationship eventually deteriorated. That was a major part of why I ended up leaving.
Looking back, I think I was exhausted by being constantly “on” more than I was exhausted by the actual engineering. There wasn’t really much separation between work and life. We worked together, ate together, hung out together, etc. And because the team was so small, there wasn’t really anywhere to retreat to when things got uncomfortable.
Sometimes I remember thinking that I just wanted to have a normal conversation with someone where I didn’t feel like I had to prove that I was smart.
I ended up leaving and joining a large aerospace/defense company about three months ago.
And honestly, the contrast has been pretty extreme.
The large company is much more stable. I have good coworkers, much better boundaries, and I don’t feel like I’m constantly being evaluated. I feel much safer asking questions or saying something stupid. I can actually have technical conversations with people without feeling like every mistake is evidence that I don’t belong.
But I’m also extremely bored.
The work is much less technically challenging than what I was doing at the startup. My team isn’t really doing ML and there is a lot of bureaucracy and slow-moving processes. I feel like I’m being underutilized and like I’m becoming a small part of a very large machine.
And I’ve only been here for three months, which is part of why I feel ridiculous even thinking about leaving already.
Part of me thinks I should just suck it up and give it more time. Maybe I’m being impatient. Maybe this is what normal employment is like and I’m just accustomed to the intensity of a startup.
But another part of me thinks I already know that this isn’t the type of work I want to be doing for very long. I’m 24, and I don’t want to spend several of my highest-learning years doing work that doesn’t really interest me just because it’s comfortable.
The complicated part is that the startup is still around, and there may be an opportunity for me to go back.
The company has gotten some real traction and is trying to raise a larger round. The technical work is still much closer to what I want to be doing. I would have much more ownership and would probably learn much faster. There is also obviously more upside if the company succeeds.
But there are a lot of complications.
The fundraising has been delayed multiple times, so I don’t know how much I should trust the timeline. The company is still extremely early stage. The same CTO is there. The interpersonal situation with the coworker I mentioned hasn’t really been resolved. And I know what it felt like to work there before.
I also don’t know how much of the environment was just a consequence of being at such an early-stage startup. Maybe things genuinely get better when a company grows. More people, more structure, more separation between work and personal life, more managers, clearer responsibilities, etc. Or maybe the problems I experienced are actually cultural problems that will just become harder to deal with as the company gets bigger.
That’s one of the things I’d really like to hear from people who have worked at startups before. Have you seen a company go from 5–10 people to 50–100+ and actually become a healthier place to work? Or do the interpersonal and cultural problems that exist when a company is tiny usually just follow the company as it grows?
And more specifically, if you were in my position, would you actually go back to THIS startup given everything that happened? I’m not asking whether you would choose a startup over a big company in general. I’m asking whether the technical opportunity and upside would be enough for you to overlook the existing complications with the people, leadership, fundraising, and my previous experience there.
I also keep going back and forth on whether feeling like the dumbest person in the room is actually a good thing. I’ve heard the advice that you should try to be the dumbest person in the room because that’s how you learn. And I agree with that intellectually. I want to work with people who are better than me. I want to be challenged. I don’t want to be the smartest person on my team.
But there seems to be a difference between being the least knowledgeable person in the room and being made to feel stupid.
I’m trying to figure out where that line is.
I also wonder whether I have overcorrected. I went from an environment that was extremely intense and psychologically activating to one that is very stable and comfortable, and now I’m wondering if I’ve gone too far in the other direction.
Maybe what I actually need is a third option: a technically ambitious environment where I’m surrounded by people who are smarter than me and can challenge me, but where I don’t feel like I have to constantly prove that I deserve to be there.
I guess my bigger question is what someone in their mid-20s should actually optimize for. Growth? Stability? Psychological health? Money? Interesting work? Good people? I don’t know how much of a career setback it would actually be to stay at the large company for a year or two, versus how much I’d regret not taking a high-growth opportunity while I’m young.
If you were 24 again, would you take the difficult/high-growth environment even if it came with a lot of discomfort? Would you stay in the stable job and use it as a bridge while looking for something better? And if you had the option to return to a startup where you had already experienced significant interpersonal and cultural problems, would you actually go back if the technical opportunity was compelling?
I’m especially interested in hearing from people who have been through this and can tell me what they wish they had optimized for earlier in their careers.

I'm CEO and co-founder of a B2B tech company selling into enterprise. My co-founder is our CTO and has built genuinely the best product in our niche (clients tell us it beats the PE-backed global incumbents). He's brilliant, but he prefers to stay in the background, so most leadership and commercial decisions end up sitting with me.

About 4 months ago we brought on a senior commercial guy as a contractor. He'd just left the biggest competitor in our space (heavily PE-backed, offices globally) where he was near director level, running partnerships. He was between roles, so we started him on a 3-month consultancy. That rolled on, and now we're formalising a proper package.

The good

He's opened a lot of doors. Super connectors, influential people in the US who shape decisions at top companies (one in particular is really bought into us), and CEOs of tech companies that sell to the same buyers we do, where we're exploring a plug-and-play partnership to win and keep those clients together.

The problem

4 months in, nothing has closed.
I know enterprise B2B cycles are long. But I can't help comparing. I have no sales background, I'm (by my own admission) a bit awkward and legal-minded, and in that time I've closed two enterprise clients myself and found partnership opportunities that could be a real multiplier for the business.

The equity

He's taking a big pay cut to be with us, and we genuinely enjoy working with him, so we want him to share in the success for taking a bet on us. We offered 4% on top of his pay. He pushed back hard and asked for 7%. We told him that's co-founder territory, especially alongside a salary, but we've agreed to it in principle.

What we're drafting so far:

• Retainer through his limited company, 12 months firm, with step-ups at revenue milestones

• Uncapped commission on net collected revenue he originates, with clawback on refunds/cancellations

• Equity on a 4-year vest with a 12-month cliff

• Good/bad leaver provisions and pre-emption on his shares  

Where I'm stuck is milestones. I want at least part of the equity tied to performance, but I have no idea what fair, contractual milestones look like for a first senior commercial hire.

What's worrying me

• He's deeply embedded because we've trusted him with a lot. He could easily walk into one of the scrappy YC-backed startups that keep popping up in our space and take these maturing relationships with him.

• Sometimes I feel manipulated into giving him what he wants. To be fair to him, influencing people is literally what we hired him for, and I own that I've let it happen.

• My co-founder doesn't want to weigh in on these calls, so it feels like I'm making them alone.  

I don't want to put this down to being a young woman in the room with a very experienced guy, but I'd be lying if I said I hadn't wondered whether that's part of the dynamic.

My questions

1.  What milestones have you used to vest equity (not just cash) for a first commercial/sales hire? Revenue? Signed contracts? Partnerships converted into revenue?

2.  Is 7% on top of pay reasonable for a senior hire at our stage, or have we overpaid? If we have, how do you restructure without blowing up the relationship?

3.  How do you protect the relationships he's introduced if he leaves? Non-solicits, CRM ownership, making sure a founder is in every key conversation?

4.  Is 4 months with zero closes a red flag, or normal for partnership-led enterprise sales?

5.  Would I be better off finding experienced B2B commercial leaders who'd get involved for equity only, as advisors or fractional?

6.  Who should I actually be talking to about this? Lawyer, mentor, advisor, coach?

7.  Any stories from founders (especially younger or female founders) who struggled managing a senior hire with way more experience than them? How did it play out?

I feel like I'm flopping as a leader right now, so any honest perspective is welcome, including if the answer is that I'm the problem. Cheers for any advice!

I spent about four years at a large firm. Well paid, very stable, but I could see AI changing my industry and I wanted to be closer to the technology rather than reading about it. Left at the end of last year and joined an early stage B2B AI startup about six months ago.

The problem is the maths. As best I can work out we have somewhere around six months of runway. They are looking to raise, but the commercials have not been the strongest, so my honest read is that an acquisition is more likely than a round.

So I have started applying to other roles. What I cannot work out is at what point should I firmly take any offer which I do get.

If something reasonable came up, would you take it purely for stability? Especially if it was at another startup (who may have longer runway but this may also happen again). Is there a point where waiting becomes the bigger risk? My worry is that if I am still here in the new year with nothing resolved, I will be job hunting from a point of desperation, especially in this market.

The genuinely difficult part is that I like the job. And it could still end fine, though even a decent acquisition may not really help me as I'm not sure whether the new acquirer will want to keep me on.

So my question is really how would you approach the next few months? Should I jump at the first job offer which offers more stability than this one? Or should I hold out for one which looks more promising (and risk being left in no man's land as the runway shortens).

If this has been asked before, forgive me. I would really like to know how everyone is validating their ideas early?

I always jump straight into design and development, its the most natural and fun part for me of course. However, getting to the end I have no way to reach people who would even want it.

My partner in crime so far just been Copilot & Claude AI, I use them all the time for software work these days. It always suggests reaching out on Reddit groups, however this has only landed me with getting a ban on a few communities.

What actually works well? Was the reddit approach correct? I always try to be careful with my postings and follow the rules, I dont promote, I dont call on anyone to visit sites or click links.

I want to get some real traction here, I cant escape the idea phase.

Appreciate any and all advice, thanks

I’m a non-technical founder building my first B2C app.

Without going too deep into the app, the idea sits around gamifying walking and making it easier/more rewarding for people to engage with nature.

I’m commercially focused, so I’m speaking with a potential CTO/technical lead and working through what the MVP needs to look like. It’s still very early - pre-product and no user metrics yet.

I’m also on an accelerator at the moment, which has made me think more seriously about what I need to demonstrate to angels/VCs before the product is live.

Right now, the only outwards facing asset I have is a very basic landing page where people can input their email (0 sign ups)

So my question is: if you were in this position, what would you focus on over the next few weeks to start demonstrating user interest?

For example:

• Build a waitlist and aim for the first 100 sign-ups?
• Start posting on TikTok/Instagram and build an audience around the problem - if so, what would I post without the product being there?
• Run small Meta/TikTok ad experiments to test whether people convert to a waitlist?
• Build a small community first?
• Focus more on user interviews and evidence of demand rather than vanity metrics?

I don’t want to manufacture a big waitlist just so I can put a number on a pitch deck. I’d rather find some early signal that suggests people want this when we launch.

I come from a software engineering background. I’m completely clueless when it comes to marketing. I’m trying to build a social app that requires a lot of people to use it for it to be useful. Would it be worth it to find a startup growth mentor from one of these platforms like MentorCruise, GrowthMentor, etc to get some guidance and support for every step of the way or should I just read books like The Cold Start Problem to figure out what to do at each step?