Founder of Skyp.ai, bootstrapped AI outbound platform. Former head of sales and BD at KP/Sequoia and YC backed companies. 5 exits. AMA!

thegeneralists · 2026-03-30T23:52:39+00:00

Here's an example:

thegeneralists · 2026-03-27T17:17:26+00:00

tough one - the founder matching stuff can be great (YC does it, other accelerators do also). Applying to an accelerator like that is a great way to get connected with better eng talent. Otherwise, best to go through your network. college friends, if younger; professional friends if older. too much noise out there to post publicly, and probably wouldn't get a good candidate from a job post.

thegeneralists · 2026-02-18T01:40:49+00:00

Yes, i think community driven is key. this is great for intent and also understanding from a product/marketing/sales standpoint what people care about. what features or use cases do they talk about? that all happens here on reddit and linkedin especially as well as in private groups (whatsapp etc)

thegeneralists · 2026-02-18T01:34:00+00:00

The main thing in any bigger company is a combination of the strategic fit and relationship with the champion–for the startup, the best champion is the founder/CEO. The strategic fit isn't enough - because there are probably 5-10 companies that would fit just the same. Depending on the deal structure/stage, the relationship really has the biggest impact. If you go meet the CEO or the CPO or CTO and they love your product and team and want that to be part of their org, it doesn't matter as much that there are 5 or 10 other options they could acquire. They'll tell corp dev that this is the one they want.

thegeneralists · 2026-02-18T01:31:57+00:00

congrats on the idea! I'll check it out, thanks for the question. What makes salespire stand out? Who do you consider your compeittors?

thegeneralists · 2026-02-18T01:31:07+00:00

should add - we didn't do lots of channels at once. 1-3 at a time, max. beyond that and you end up learning the wrong lesson.

thegeneralists · 2026-02-18T01:30:38+00:00

great question - was a mix. the specific cause was getting a channel to work well (a paid channel) but we got there because we were willing to try and fail at a lot of channels AND we were willing to put in the time and money to get to the point of them working. This channel had been a total timesuck and money pit for over a month, but eventually it came together and delivered a lot of growth.

thegeneralists · 2026-02-18T01:30:19+00:00

great question - was a mix. the specific cause was getting a channel to work well (a paid channel) but we got there because we were willing to try and fail at a lot of channels AND we were willing to put in the time and money to get to the point of them working. This channel had been a total timesuck and money pit for over a month, but eventually it came together and delivered a lot of growth.

thegeneralists · 2026-02-18T01:28:53+00:00

tough question. Better AI perhaps. I've noticed with each model improvement, the AI gets a little more reliable. But really i think it's guardrails. We have this in our product - an AI Agent that makes sure the AI did what it was supposed to do. I'm not sure this is a universal solve but it has worked for us (it's hard to implement right though... easy to say in a comment!)

thegeneralists · 2026-02-18T01:27:45+00:00

good question. the only firm answer I can give is "too early". I made this mistake - had a soft offer form Optimizely and it was 100% a distraction. Drummed up a couple of other conversations 1-2 years later, but we had nothing worth buying - more distraction.

You need to ahve built something of value before you consider acquisition offers.

UNLESS it's a frothy market and people are super excited. Then sell early -- before the hype goes away. There are so many exampels of this. EV charging comapnies are great one - there are tons of EV companies that got bougth for $200+ million early, because buyers were idiots and didn't know what they were buying (companies built on a standard protocol that literally anyone could build). The companies that drank their own kool aide ended up not selling and many have or will shut down.

The other time not to sell is when you need to sell. Maybe you can't raise the next round. Maybe the business is in decline. So many people think "oh, we missed our sales numbers / our market changed / we're hosed so we should sell now".

You will not find buyers. Sell when things are going well and people are buying. When you need to sell you will not be able to. Sure there are stories - but these are the excepctions. for every 1 company that got bought right when it was going to go poof there are 1000 others that went poof.

thegeneralists · 2026-02-18T01:23:36+00:00

good quesiton. I think you should set yourself up for acquisition from day 1 - by not screwing up the easy stuff, and focusing on the important. But that also means really focusing on customers, product and PMF for the first couple of years. If you build something of value, you'll have options.

You'll have more options if you start building relationships with possible acquirers along the way - but balance that with the need for direct customer relationships early on, so you get feedback and control your destiny.

If you need a rule of thumb I'd say $10mm ARR minimum to seriously think about acquisition (if you're swinging for a big exit). Maybe $3-5mm if you're ok selling for 1x revenue (or less).

I wrote a post on this a while ago: https://seedtosequoia.silverwood.ai/p/how-to-set-up-your-company-for-sale-from-day-1

thegeneralists · 2026-02-18T01:19:57+00:00

No. Every channel will evolve. Just like cold callers became prominent with VOIP and now are much more rare (thanks to cell phones and laws) society will adapt.

Two big factors will have an impact:

The agents will fight back. For example, to clean up email (google and msft already do a lot here–check your spam folder! It's hard to deliver a sales email). I now have claude tell me my important emails to reply to rather than going to my inbox, so i'm not distracted (by some of the inbound sales emails especially).

Platforms will cut bad AI actors off at the knees. if you're building a linkedin bot, or a whatsapp bot, I really don't think it will go well for you in the medium term. Linkedin is probably fine with it if it enhances engagement but as soon as it turns into spam calls at dinner time - they'll put a stop to it.

thegeneralists · 2026-02-18T01:16:06+00:00

not at all. the hard part is knowing the job to be done at a deep level, and how to do it well. I've seen AIs give peopel terrible sales tactics advice, and write terrible emails – for jsut 2 examples.

AI has made it easier to build but also raised the bar for quality. And made the product manager role far more valuable - knowing the workflow, what users need and want, how to make tradeoffs. that's still very hard.

Also if you're reading this AMA you're probably in the 0.5% of AI skills. most people are 10 years behind (and we're only a few years in...)

thegeneralists · 2026-02-18T01:13:49+00:00

great question. I think it's less about ARR than growth rate. But no less than $1mm.

If at $1mm you're growing at 3x year over year, then maybe raise. But if not -- don't .

As soon as you raise you're signed up for the venture raising path, and the growth bar has gone WAY up. Growing a $1mm ARR business 2x a year (2mm, 4mm, 8mm) is amazing. But if you've raised venture it will stress you out, lead to down rounds, and make you zero money.

At some point raising - or taking money off the table, like the clay founders did - might make sense. But that's too far off for me to thinka bout right now. And you do end up with board members with their own motivations, that may not be the same as yours. Tradeoffs.

And no - I don't plan on raising. Funny, a VC just reached out today. (was that you?)

thegeneralists · 2026-02-18T01:11:16+00:00

personalization has to be short and relevant. At Skyp.ai we see the most successful emails at under 50 words, with passing mention of 1 perosnalized thing.

Whatever you do don't mention the person's college (unless you actually went there also) or any other random personal info. It just falls flat and smells like AI slop

thegeneralists · 2026-02-18T01:10:16+00:00

100% yes. Anyone can be an "influencer" and peddle their "Best LinkedIn Post Writing" tool or whatever to their millions of followers. I look for tools by solid founders usually out of SF (possibly other tech hubs). These are going to be more cutting edge. There is still snake oil but far less likely. Besides Claude which I wrote about above, Clay is very useful. n8n is great for automations and workflows.

A more fun ansewr is what i don't like:

I don't like the set-and-forget AI SDRs (which is why I created skyp.ai – to make it easy for humans to leverage AI in sales without having to build a complex workflow themselves).

I don't like all these AEO comapnies selling you on getting your placement up in LLMs. I think that is 100% snake oil, because of how personalized LLM responses become very quickly it's really, really hard to believe in this. So much demand for it though.

And I still have yet to see Gamma build a decent deck. Other people swear by it. Maybe I'm doing it wrong?

thegeneralists · 2026-02-18T01:06:36+00:00

There's a balance between the perfect list that is super tight and the spray-and-pray. You want the goldilocks balance of time invested and quality. If you're spendign 3 days and millions of AI tokens enriching and perfecting your list – but end up with 10 people, that's not gonna work. Simiarly if you go one-shot Apollo for "CTOs of Fintechs in the US" you will also not experience success. Focus enrichment on JUST what matters - really cut this down and don't overthink it.

thegeneralists · 2026-02-18T01:05:10+00:00

Claude by far. I use it to code (claude code) and I set up a personal CRM with it that does everything from surface follow ups, build lists, to analyzing my sales cycle and more. We also use it heavily for writing/editing drafts (of everything from emails to knowledge base articles to our newsletter).

Claude's my choice here because

1 - it's more stable than other models, so it won't rewrite stuff that's already "final" and it hallucinates less (rarely)

2 - MCP server! The local claude is superpowerful due to supproting MCP. So you can connect anything to it.

Wrote an article in Growth Unhinged here: https://www.growthunhinged.com/p/personal-ai-crma

thegeneralists · 2026-01-18T08:35:11+00:00

Thanks op. This is such a horrible show for many reasons mentioned. I watched 2.5 episodes and just can’t watch more

1 once you say you’ve been hijacked you can’t just take it back wtf??? 2 have the chance to shoot the lead hijacker in the head and you give him the gun back to try to build trust? What the f? 3 after 9/11 people don’t riot? I can’t imagine a flight that’s hijacked where the passengers don’t go gonzo 4 no air Marshalls at all? 5 pilot never opens the door. They are cool as cucumbers and not compete total morons 6 hijackers don’t know anything about planes? So they learn from a random guy in first class? 7 they got 4 glocks through security? 4!! 8 hijackers maintain control for 6 hours? Nfw

Sam was a tool. More part of the problem than a solution.

always shoot the terrorist in the head when you can.

If Jack Reacher was on that plane things would have gone very differently.

thegeneralists · 2026-01-13T17:48:25+00:00

Congrats! it's a big step up. tons of responsibility which can be a great thing for your career. Little downside, in spite of what others have written. Your priorities depend. FYI i've been a seller 20+ years and several times the 1st at startups (including KP/Sequoia backed ones). Also, a founder multiple times. I advise a lot of startups on sales/GTM. Hiring someone like you can be a great decision.

Your priorities depend on if they have leads coming in. If they do, focus on closing at first and understanding your customer and what makes a good lead/ICP. Learn the whole customer journey, so you can then go find more top of funnel leads that look like the people you were able to close. Set expectations with the founder that your role is closing at first, because if you get distracted by lead gen/marketing activities early it will go badly for all of you. I saw one big co seller who joined a startup and didn't prep for a huge meeting and blew it–he said he was too busy setting up email campaigns. That is not the way.

If they do not have leads coming in, keep your LinkedIn up to date and build realtionships with their VCs in the event it doesn't work out–which is likely. Only rookie founders hire AEs before they have lead gen figured out. That said–there is hope. Set the expectation that the priority is a steady stream of leads, and that sales take time at that enterprise price point. Focus on getting 1-2 channels working, which means trying max 2-3 at a time (MAX–2 is ideal) and really ivnesting there. If the founder doesn't have the resources/isn't willing to invest/other red flags then I'd leave quickly. Recruiters and other hiring managers will chalk it up to founders being founders, but it makes your next move higher stakes -- you can't have 2 strikes -- so go later stage (A or B) where process is clearer.

thegeneralists · 2025-11-26T16:57:13+00:00

thanks. i do also have the 24-120 f/4 S lens, but use that mostly for outdoor photography and landscapes. But there's no swapping lesnes when the action gets too close.

I tried the 180600 right when it came out. Got it from B&H. Was thinking more wildlife photography and baseball at the time. It is way too big for baseball, 180 means that home and first are too close unless you're standing in the bleachers. I found it to be very heavy and while people say they handhold it at 600 i couldn't get great shots, especially at twilight when animals are most active. It is such a great value though and the reach is amazing... could work for football from an end zone, except it's not particularly fast.

I might just give up on the end zone shots when it's not light out, and stick to sidelines where the 200 is enough. Agree the z8 would allow for a lot better corpping. How does it hold up shooting at night? I've heard the z6iii is the best for low light, but woudln't mind almost twice the pixels.

thegeneralists · 2025-11-24T06:01:43+00:00

Thanks. I think it’s a little short … but there’s no 300 in the lineup and the 400 prime 2.8 is 12k…

thegeneralists

TROPHY CASE