Send Me Your Hardest SaaS Question

0:00A lot of things are changing in SAS right now. AI has rewritten how products get built, how marketing works, and how founders decide what to even build in the first place. When things move this fast, generic advice can only take you so far. I've invested in more than 240 SAS companies, and I talk to founders every single week, and the ones who break through are good at asking great questions. So, I want to try to mix it up a bit on the channel, and instead of publishing another framework video, I want to lean in and I want to get specific based on your questions. But that only works if you know how to ask a

0:33productive question. So, I'm going to start by giving you some thoughts and then tell you how you can ask me questions. So, let's start with how to ask a great question. Let me give you an example of a question that I won't answer. How do I market my SAS? The answer is, I have no idea. I don't know if you launched last week, if you're at 40k MRR, if you're doing 5 million a year. I don't know if you're selling to enterprise security teams or dog groomers. I don't know if you've already run three channels into the ground, or if you've never sent a single cold email

1:00or done any SEO. All I can do with a question like that is give you the generic answer, and the generic answer is already all over this and other channels. So, here's the same question with context. I'm at 8k MRR. I'm B2B. I sell scheduling software to HVAC contractors. I ran cold outreach for 3 months, sent about 2,000 emails, I

1:19booked 14 calls, I closed two customers. I'm trying to decide whether to keep pushing outbound or move that time into SEO. That one I can answer. And I can answer it in a way that's actually useful to you, because now I know your stage, have an idea of your market, what you've already tried, what it produced, and the specific decision that you're stuck on. So, when you send me a question, give me four things. The first is the situation. So, like, what are you building? Who's it for? And roughly,

1:45where are you? MRR, the stage, B2B, B2C. Second thing is what you've already tried and how it went. Give me numbers if you have them, and guesstimates or your vague recollections are probably better than nothing. The third thing is tell me what you've deliberately decided not to do and why. So, if you've ruled out paid ads because your annual contract value is $300, you can tell me that. But otherwise, I'm going to suggest it and waste both of our time unless you tell me you've already ruled something out. The fourth is tell me the actual decision you're stuck on. So, not the topic, but the decision, right? So,

2:19you can say I need help with pricing. How should I price my SaaS? Or you could say should I raise my entry tier from $29 to $49 when 80% of my customers are sitting on it. That's a decision. So, the more context you give me, the more specific I can get and specific is the entire point of doing this. Now, with all that said, you also can't send me a novel. You can't send me a 7-minute video or audio question or a 2,000-word question. So, you do probably want AI to help you summarize or edit yourself relentlessly. The second thing is take a

2:49few swings before you step up to ask me. I find it really hard to help a founder who hasn't tried anything yet. If you tell me you're stuck getting your first customers and I ask what you've tried and the answer is nothing, there's just no thread for me to pull on. Like there's information on this channel already about how to do that. How to find your first 10 customers, how to find your first 100 customers. At that point, you're asking a generic question and it'll get a generic answer. And more broadly, if your question is really general, there's a good chance I already have a video about it. How do I find an

3:17idea? Done it. How do I price my SaaS? Done it. When do I make my first hire? Video on that. Should I raise money or not? Done it. So, it's all on this channel, right? And some of it I've been refining for 15 or 20 years. This channel plus Startup for the rest of us plus the six books that I've written, they'll answer all the general questions plus some. So, please do the homework and look at that content before you ask a very generic question. What I want are the questions that those videos and all the content that I put out doesn't answer. I'm obviously not saying that to

3:49brush you off, right? The fundamentals are the best starting point you have and they're free and they're right here. They're available. What I can add on top of that is the judgment call. It's the detail. It's the part where my standard advice doesn't quite fit for your situation and you need someone to help you think it through. My favorite questions sound something like this. I watched your video on this particular topic. I went and I tried that. Here's what happened and here's where it fell apart. That's a great question. I can do something with that. So, with all of that context, here's what I want you to

4:19do. Go to robwalling.com/questions and leave me your question with the context I just talked about. And you can certainly ask more than one. I'm going to pick the best questions and I'm going to answer them right here on the channel. One note on format. If you send video or voice, [snorts] you're going to go to the top of the stack cuz hearing you ask it in your own words tells me things a paragraph of text can't. Where you're frustrated, where you're actually worried about underneath the question, and it's just more interesting for viewers and listeners. So, if you're willing to turn on your camera or record 60 seconds of

4:50audio, do that. If you'd rather write it out, it totally works, too. I may have an AI voice read it for me on the channel and yes, I'm aware of the irony of doing that. So, submit your questions and then subscribe so you see the answer when it goes up. I just might answer your question in a future video. Before you send me a question, it helps to actually know where you're at. So, if you're not sure what stage your SaaS is, watch this video next. Make sure you hit the subscribe button so you can get notified when we start rolling out the

5:17answers to all your burning questions. Thanks for watching and we'll see you next time.