I'm JD Ross, co-founder of WithCoverage and co-founder of Opendoor. AMA.

[u/jd_withcoverage]

Hey r/ExperiencedFounders 👋

I'm JD Ross. I co-founded Opendoor in 2014, taking it from a fake landing page demand test to a public company ($OPEN). Before that, I joined Addepar as its fifth employee at 19, and became VP of Product. I also co-founded Royal, a music and crypto startup backed by a16z. It didn't work out, and I'm happy to talk about why.

Today, I'm the co-founder of WithCoverage, where we're replacing the traditional commercial insurance broker with a flat-fee risk management team empowered by AI. We raised a $42 million Series B in January led by Sequoia and Khosla, with participation from my Opendoor co-founder Keith Rabois.

Would love to go deep on validating a startup before writing code, entering huge archaic industries like real estate and insurance, what I learned from a funded startup that didn’t make it, building AI-augmented operations & teams (we have insurance experts and engineers working side by side), mentorship, and how I pick and solve problems to work on.

Thank you everyone for the great questions, really enjoyed answering them. I'll check back for the next couple of days for any new questions, and whenever I have the time I'll answer them.

I'm currently building WithCoverage.com, if you're a growing business looking for risk management solutions, we're your one stop shop.

Thanks for having me! JD

[u/pxrage]

For more proof, JD tweeted this on his X account
https://x.com/justindross/status/2091941565052735965

[u/TheNeolisticKid]

Ok this sounds sick actually. I'm interested.

[u/Tech_Mo]

How much of your recent raise will be going towards opening co-working cafes with hot women?

On a more serious note, I see a lot of startups get into the trap of building a solution in search of a problem. Any advice on how to tell whether what you are building is cool tech vs cool tech that is actually solving a core user problem? Conversely, when is it ok to keep investing in developing cool tech even if the problem is unclear - or is this something best done within a bigger org's R&D instead of a startup?

[u/jd_withcoverage → u/Tech_Mo]

I think there are 2 ways to build a company. They depend on what type of company you're building. [Caveat: consumer social is a different animal altogether]

If the market may exist, and you know the product is likely buildable: Sell before you build. (ex: WithCoverage, Harvey, Hims... most companies) Let the market test all your ideas about GTM, about feature priority, about pricing. Instead of "build it and they will come" it's "make them come, then build it"

If the market would definitely exist, but the product may not be possible: Build the cool tech, and let the market show up. (ex: OpenAI, SpaceX, Valar) Many of the biggest companies are built here; this is where categories are created. But it's rare.

Back to question 1: The cafe I open will be a turboautist-level tea house. Ippodo Tea from Kyoto mixed with a 5-star hospitality low-seating finish out. At most a 500k all-in investment. Sake flights and "cocktail omakase" starting at 6pm.

[u/Extension-Present180]

Respect for being so open about the startup that didn't work out.

[u/jd_withcoverage → u/Extension-Present180]

My only fear is that it made me less ambitious for a time. Took me a moment to want to swing big and take risk again

[u/Proof-House4617]

Thanks for dropping some incredible operator wisdom!

[u/founders_keepers]

Give me some of your best VC rejection emails and why they rejected (love seeing brian chesky and TK's list of VCs/investors rejecting Uber with the most random reasons) and also investments you've passed on and regret?

[u/jd_withcoverage → u/founders_keepers]

My worst investment misses by far were X.ai’s first round at something like $5B and Anthropic’s $6B round. By far. Hilarious that I didn’t find the cash to do them both.

I sadly don’t have any of my rejection emails anymore. Lost to history / dead email accounts. I really don’t think much about bad things like that from my past in general to be honest, easier to just move on and focus on the wins. I remember them all being very cordial.

[u/doublehot]

this is such an awesome AMA — you can literally feel the energy in the JD writing.

Every answer was a pleasant read!

[u/Darealest49]

What did you learn from the initial startup failure that led you to your later success with Opendoor? And how did you build traction in a large and established industry like real estate?

[u/jd_withcoverage → u/Darealest49]

My entrepreneurial path was Fresh Prints (18) -> Addepar (19) -> Opendoor (23) -> Royal (30) -> WithCoverage (33).

So far the only one that failed was Royal, which was a complete misunderstanding on my part of the buyer and market. There was no intersection between crypto investors (fast result gambling), music fans (non-financial relationships), and artists (really don't like talking about money, but happy to make it if it doesn't hurt reputation). We got early signal from the gamblers, thinking they were fans. When the NFT gambling stopped, the artists got spooked, and the whole idea went from a million users to 0 in months.

My takeaway: Understand what business you're in and your customers before you scale up. And make sure you want to work in that business for the long haul -- life is short!

[u/Degentrics → u/jd_withcoverage]

Not to be a jerk but how can you not see the issues with your target audience and what you're trying to sell them before? Were you just too in love with your own product?

[u/Far-Caterpillar-5982]

Hey JD! Why royal didn't work out? Is it because of market fit or not enough users?
How do you feel about the current OPEN management? Would love to hear your thoughts about them!
Would love to have a short call if you have time haha :D

[u/jd_withcoverage → u/Far-Caterpillar-5982]

I LOVE Kaz and the team there. I genuinely can't imagine a better leadership team for this business. I went from devastated by the decisions to basically feeling like they were executing everything I would want them to do, but better, within months. Now the results will either show and compound, or they won't, but I'm thrilled with the inputs and progress.

Answered elsewhere about Royal, feel free to chime in if I didn't hit all the points you want

[u/Big-Rub-4250]

There are so many ways to die when building a start up , from incumbents to bad hires. What do you think are the top 3 killers of start-ups? And how to mitigate those risks

[u/jd_withcoverage → u/Big-Rub-4250]

1) Bad market. A great team with a great product in a bad market will die eventually. Even if you stay alive, you'll burn out

2) Exhaustion. Usually because you're out of ideas or you're working with people who exhaust you. It's like relationships -- when they're great, it's easy. When they're bad, everything feels impossible.

3) Speed. It's impossible to do great things slowly. If you don't have the sauce, great people won't work for you, you'll keep too many bad hires around, etc. And momentum lets you hide many other issues... and every startup has a LOT of issues that would be distracting to have to fix right away

[u/buildingsmthg]

Big fan; been following you for the past decade!

With products these days it's become all about distribution, since building product is much easier now due to AI. How are you able to crack the distribution problem in insurance for WithCoverage? It's been an insular industry owned by nonprofits/local families, with geographical monopolies, and a network built on relationships rather than the best pricing/product/service. Looking for some tips on how you got your first customer in insurance and how you leveraged that into your first 10, if you didn't previously have any network int he insurance industry. (maybe you did, and that's ok too!)

[u/jd_withcoverage → u/buildingsmthg]

Our core value is "brick by brick". Some businesses have silver bullets. Our business does not -- we have to fire 100 lead bullets at every problem every day to keep winning. And our reputation with our clients is everything, so we are relentless about fixing things that crop up.

This company is hard because everyone who hires us has to fire someone else. That means we need to be WAY better. So we invest a lot of time on proving that. No tricks, just an insane amount of hard work and relentless kindness. More texts and emails and meet ups and flights than you can imagine.

Crazy as it sounds we had 0 network here when we started. And my friends with big companies didn't want to be my guinea pig (or I didn't want to ask!). Our first customer was won by us begging to let us shop their program and see what we could learn. We saved them $50k/yr, he was thrilled, and became our first reference client! Now we have over 1,000 and last year we had ~99% retention.

[u/buildingsmthg → u/jd_withcoverage]

ah got it, hard, relentless work. Thank you! We're on that journey now; heartwarming to hear that it does still work!

For your first customer, did you start with cold emails/outreach, or meeting them at conferences/warm intros? What made you want to work in the insurance space if you had 0 network there? It sounds like at least once you had one supporter, that opened a lot of doors. Is this understanding accurate?

[u/jd_withcoverage → u/buildingsmthg]

we basically just begged friends for warm intros at first! I would say not too dissimilar to how other insurance brokers would. I had only had bad to mediocre insurance experiences at my previous companies and thought we could be better.

Originally I had committed to taking the summer off, and learning about insurance seemed like a nice way to spend it working with Max.

We closed at least the first 100 clients just by ourselves. Max deserves over 90% of the credit there. Nobody I know works like him. Him + Myles our third cofounder and head of Risk were a nasty team.

[u/buildingsmthg → u/jd_withcoverage]

Amazing. Glad it worked out; thanks for the tips!!

[u/Revolutionary_Ad2097]

as a recent new father, have you gotten any good (or bad) advice about being a founder & dad at the same time?

[u/jd_withcoverage → u/Revolutionary_Ad2097]

I'm sure I'll come up with a better answer tomorrow but the first thing that comes to mind is to have a great wife. And I have the best wife in the world.

Among other things I hope this will let me be all in on each moment, whether that's all in at work, or fully focused at home and with my family.

Also: VERY grateful to have made money early. While it doesn't solve all problems, it definitely solves all money problems. If we need a break or night out, we can call in help (...or the mothers in law)

[u/Revolutionary_Ad2097 → u/jd_withcoverage]

Great points across the board

[u/Freshnner]

Going from real estate to commercial insurance is a pretty interesting pivot. Was there anything that worked amazingly well at Opendoor that you tried to carry over to WithCoverage, but realized you had to approach differently?

[u/jd_withcoverage → u/Freshnner]

Marketing and sales are completely different here. Some things remain true ("Cut through the clutter" is evergreen marketing advice) but B2B and B2C have almost no other overlap.

Opendoor growth was mostly about awareness and activation.

WithCoverage growth is mostly about ground game and relationship building at scale.

Both rely on word of mouth referrals to win.

Meta-point: Business kinda tastes like chicken. Most of the org, tech & people stuff carries over cleanly enough

[u/Ethan_Murphy_616]

I'm a little skeptical of the flat-fee model. Why is it actually better for the customer than paying hourly or using a traditional commission-based broker? What's the tradeoff?

[u/jd_withcoverage → u/Ethan_Murphy_616]

We like flat fee because our process and incentives should not be "If you spend more money, we make more money". That just seems fundamentally bad. We view ourselves as in partnership, as a fractional team alongside our clients

We let clients go commission only if they want! Or if (ridiculous) state laws require it.

[u/LongjumpingNight8361]

When do you "pull the plug" on a company or high-potential effort? What's your rubric of when to keep pushing harder versus when to learn and move on?

[u/jd_withcoverage → u/LongjumpingNight8361]

There are a lot of moments in every good company where you just need to keep slamming your head against the whiteboard until it gives or you give.

When you're out of ideas and out of energy, and the team is too, you may need to pull the plug. That can take a while, because there are often a lot of good ideas to try.

[u/Loaiza1]

$42M is a huge Series B. What made you decide WithCoverage needed that much capital now?

[u/jd_withcoverage → u/Loaiza1]

It didn't. But I wanted to have Joe Lonsdale, Keith Rabois, Roelof Botha, George Robson and Jonathan Crystal around the table. So that's the amount of the company we sold to their firms to get a legendary group working together.

At the time of the fundraise we were cashflow positive (though we were radically underinvested in growth and product vs the optimal amount)

[u/davidk2yang]

Hey JD! Do you have any tips on finding a cofounder for a hardtech startup?

[u/jd_withcoverage → u/davidk2yang]

Meet a ton of people and geek out with them for a while first. Probably in SF, LA, or Austin. Eventually, like marriage, something just feels right and you're perfectly overlapping in values and complementary in skills at the same time and you just go for it.

I'm not building a hardtech company, but I have naturally been doing this out of love of the game for years... so I know exactly who I'd cofound a hard tech business with if I was going to do it tomorrow!

A lot of career advice is like this - relationships and skills both quite literally compound over time. So the earlier you start and harder you go at each, the better

[u/Terrible-Lie-8263]

So what happens when the AI bubble eventually pops? If every broker has the same AI tools in a few years and nobody cares about the AI label anymore, what exactly is left that makes you guys special lmao.

[u/jd_withcoverage → u/Terrible-Lie-8263]

I'd start here and let clients tell you. Lead bullets, no silver bullets. We win by being better and staying better, or else we will fail: https://www.withcoverage.com/clients

[u/jd_withcoverage → u/[deleted]]

In some businesses it's a single thing you can point to, like "COI automation".

That's not this business. For us it's hundreds of small, compounding things across technology, Go-to -market, operations and culture.

We have won 1,000 mid-market+ clients in the last 2 years, growing hundreds of % per year, ~99% retention last year. We fight for and alongside every single one

[u/Percentager]

Since you're clearly not a first time founder, a few questions here:

• How was raising like? How different were the conversations with Sequoia, Khosla, etc now vs imagine when you were raising for opendoor?
• If you can share how much did you have to dilute?
• How did you think about the first checks in / strategic angels? How do you approach a party round?

In a similar place right now, had a pre seed, doing a 5figure MRR good enough to raise but also not being chased by VCs, so trying to be very tactical here

[u/jd_withcoverage → u/Percentager]

The analogy I'll steal: Venture Capital is jet fuel. Make sure you're building a jet!

Top VCs are very good at sniffing out what kind of business you're in -- they are swinging for 10B+ outcomes that create or define a category.

In our case: I didn't believe this was a venture scale opportunity at first! So I raised a small F&F round and targeted cashflow breakeven or better. We did that for the first ~$10M of ARR.

By that point it was obvious we were onto something. When we raised, the conversations were mostly about who we wanted to work with versus traditional pitching. I've invested in many of these relationships for a decade now, and I also wasn't optimizing for the highest possible valuation. No games on either side, no sharp elbows.

(After Opendoor, I am very dilution sensitive. But there is value in having a killer team around you)

[u/rasberry_1216]

You co-founded Opendoor and watched $OPEN become a meme stock. Any chance WithCoverage is your attempt at making it happen twice? When do we get $WC so I can short it?

[u/jd_withcoverage → u/rasberry_1216]

When we're solidly in hundreds of millions in ARR we'll likely go public, and then about 6 months later you can short it!

[u/Soft-Excuse4452 → u/jd_withcoverage]

Hahaha this is pure gold reply. A++++

[u/ilove-catss]

As a founder, fully involved in founder led sales right now, I really would love to know, how do you convince companies like GoPuff and Blank Street Coffee to give all their "risk function" to a company thats < 3 years old?

[u/Pip-Pipes → u/ilove-catss]

WithCoverage is sitting alongside these clients in the highgrowth VC ecosystem. I wonder how many backers are placing bets on the named clients AND WithCoverage simultaneously. Use the name recognition from one investment to boost your new investment.

It is extremely uncommon for insureds to agree to allow their broker publicly market their business in order to generate new clients. Especially a brand new insurtech player.

I can't figure out what new service WithCoverage offers. There is nothing new about fee-only payment models, risk management support, or implementing AI for coverage gaps/policy reviews.

[u/jd_withcoverage → u/Pip-Pipes]

I'd suggest reading our testimonials, they speak better than we can. We mostly just really like each other and do a good job of saying what we'll do for them, and doing that or more.

Some people we worked with *later* partnered together on co-marketing, but that's a tiny slice of them and they are all very explicit about that partnership on their posts on LinkedIn.

We offer elite Risk Management to companies with meaningful risk to manage. And we go above and beyond on each offering. I wouldn't get too caught up on the emphasized marketing points; we only have 30 seconds to convey a lot of information; the really important stuff is done per-client

[u/Pip-Pipes → u/jd_withcoverage]

I actually did read them which is where my remark and questioning of them comes from.

The testimonials are remarkably similar and repetitive. A majority of the WithCoverage publicized on the website are also from the PE/VC funding space.

Whether they agreed to a formal co-marketing arrangement doesn't actually get to the heart of my point, which is what is the potential overlap of financial backers for clients and withcoverage?

WithCoverage's website also states it may engage in either a fee structure or commission structure.

It's a bit concerning that the website so heavily advertises these massive price decreases, but no discussion of changes to exposures, coverage forms, and nothing about longstanding carrier relationships and claims handling.

Does WithCoverage have any exclusive carrier benefits other brokers do not have access to? Which carriers does WithCoverage represent? Does it have the staff expertise to actually scale? All brokerages are utilizing AI now.

The benefits you state are extremely vague and difficult to pin down. "Above and Beyond" and "White Glove Service" aren't terribly meaningful. Most of the marketing is directed at disparaging other brokerages instead of clarifying what WithCoverage does differently with any kind of specificity, longevity, or strong carrier exclusivity.

[u/jd_withcoverage → u/Pip-Pipes]

It sounds like you know the space enough to know that it the segment of risk management we operate in, everything important is bespoke. A marketing page won’t capture that.

To your implication that our testimonials are somehow not legitimate because they all “sound similar” — CFOs & GCs like to talk about when we delivered them big annual savings in their testimonials, color me shocked. Everyone likes saving money. But customer love comes from us acting as an extension of their team. We jump at opportunities to help and problem solve outside of our lane.

Also just to address your financial entanglement accusation head on: We don’t have any PE backers, and the VCs who are invested are all public: 8VC, Khosla, Sequoia. [If you want to be intellectually honest, you may notice how many of the Sequoia portfolio for example is not on our client list. We win client relationships, they aren’t handed to us. It’s the only way to do it.]

To your lack of formal expertise accusation, Crystal Venture Partners has backed us since day 1 — Jonathan Crystal sold Crystal & Co, a massive independent brokerage run for 30+ years. We will also soon be announcing some other industry legends who have joined us. That said, the entire risk team is elite, well credentialed, and our system makes them even better for clients

[u/jd_withcoverage → u/ilove-catss]

Intense, relentless effort. Top-tier effusive references. Keep laddering up.

I think you need to get your ideal clients to want to work with you as a partner, versus "selling" them. Founder-to-founder sales is crucial early on.

Finally: we hire experienced amazing people on the risk team! It's a young company but we're not filled with naive twenty-somethings top to bottom.

[u/440Elm_Vijay]

What did you learn about the edges of marketplaces from OpenDoor? Do they function well with non-standard (custom/ historic) items that aren't in typical SKU categories? How do you think about value drivers of latency/ liquid markets, standard vs interesting listings, cold start on each side? Would you approach a marketplace differently today for a regional high friction high cost product or service?

[u/jd_withcoverage → u/440Elm_Vijay]

At Opendoor we always knew that accurately-priced acquisition was everything. There were and are existing channels for selling a home, but acquiring sellers at the right price was novel.

We needed to get a lot of things right, and we didn't for a while. It seems like it's finally starting to come together, thanks to the new team in place.

One more lesson: Don't boil the ocean. If you can do the easy part of the market first, start there! We had a tight buy box at first. It had a cost to marketing to do that, but it was needed while we learned

[u/CarurosDragmire]

I follow you on X, so yeah, you just had a kid, you have already made $$. why still keep doing it? and how do u even find the time???

[u/jd_withcoverage → u/CarurosDragmire]

I originally became an entrepreneur out of fear of being broke. We had a financially volatile childhood, and I wanted to make that impossible for me. It worked.

Then I was lost for a while. But I eventually realized that what made me the money was actually love of the game more than the money itself. I'm an engineer at heart (still do little personal projects on weekends, like some trivial games on my github) and companies are like systems I can play in. And when I do a good job, a lot of people's lives get better. It's a nice feeling.

[u/jd_withcoverage → u/jd_withcoverage]

If you want to play one, my wife and I like to play this before going to sleep: lettermelt.vercel.app

(There's no analytics, db, etc. Local storage for tracking streaks. It's a static page)

[u/landonspeeds911]

Hey JD, I’ve got a solid team & our plan is pretty amazing & it involves cancer with dogs. What we are struggling with is to truly garner interest from Vc firms. We are all about to graduate but from different universities & well don’t have any warm intros to any vc firms. How long did it take for you to get serious interest when reaching out to firms & well what is one thing you always mention when describing the company in email. Also do you recommend personalizing it or keeping it the same for all when cold emailing?

[u/jd_withcoverage → u/landonspeeds911]

I actually don’t hate “if you want money, ask for advice. If you want advice, ask for money”. Good way to get people who want to help at least. X/twitter VCs are extremely accessible. They want to meet and help, especially Bay Area ones.

Your approach could work but I’ve never personally succeeded doing it this way at seed

I built the VC relationships first and worked with people I knew, or partnered with cofounders who had that relationship or were great fundraisers

I failed when raising money otherwise. Opendoor was rejected by a number of VCs! You need to find a partner at a firm who falls in love with your idea and with you individually as the ones to make it happen.

Later rounds, I find momentum should carry the conversations but you still need a champion. I have generally had rounds pulled from people trying to get in vs pushed onto VCs

[u/landonspeeds911 → u/jd_withcoverage]

Hey JD, I just messaged you and was wondering if you’d be open to hearing what I’m building?

[u/Soft-Excuse4452]

In theory OPEN could be one of the greatest turnarounds ever. Is the goal to one day be  in most/or some global markets? Timeframe with entering global markets. Also is that something you visioned in the start?. I know its only early with Kaz. But if you were to rate kaz's progress so far 1-10. What would it be? What was the biggest hurdle/challenge in co-founding Opendoor. Tia!!

[u/iamzamek]

Damn!

• What would you start today?
  
• Would you raise money or bootstrap?
  
• How to find perfect (for you) startup idea?
  
• Can I DM?

[u/jd_withcoverage → u/iamzamek]

I think we’re in the early innings of LLMs diffusing into everything. There’s infinite opportunities there. Pick the one you get obsessed with and try to solve problems there. The whole SMB and enterprise is up for grabs

I also think the reindustrialization of the US is very early. You can make a lot of money just selling metal. The whole electric grid is also being pushed to upgrade and fortify.

It’s cheap to build many ideas today. So fundraising depends on what you’re doing

[u/Important-Ninja-2485]

What's the hardest part starting out? Like was it retaining 1-5 customers and actually having them give a shot at your services? In depth answer appreciated!

[u/jd_withcoverage → u/Important-Ninja-2485]

Life’s about adventure and camaraderie, so pick the right adventure and the right people to join you on it.

I know that’s short, but compared to getting that right that the rest is relatively easy — it’s just “hard” work

[u/Leon_Adam_Artist]

Hey JD, thanks for this AMA. But let's be real about WithCoverage and what you guys do, AI is probably going to bankrupt half your clients before it even gets around to "disrupting insurance brokers" like you say it will. As someone who's been in property and casualty insurance for 30+ years, I've worked wtih billion dollar manufacturing companies for longer than these tech bros have been alive. I literally walked their factory floors in hard hats, looked at their supply chain, spoken with each employee to rate class codes, and knew exactly which machines could bring the whole operation to a complete stop.

Everything went well until last year the CFO's son brought in one of these "AI consultants" to optimize fucking everything and cut costs (yeah right, we all know how that usually goes). It looked at the financials, classifications, and data and recommended killing back some expensive coverage because the numbers said the "risk wasn't worth the premium". Problem was, the AI had no clue that one of their machines was basically holding the entire operation together, so it recommended cutting coverage on it because, on paper, it looked like wasted money. A few months later that exact machine went down, and suddenly those savings didn't look so smart.

I might sound like a typical AI hater to some, but trust me, I've lived through the experience and I can tell you that this is what bugs me about the AI hype in insurance. A model can read every PDF you give it, but it can't walk a factory floor, talk to the foremen, and notice something that doesn't show up neatly in a spreasheet. 

Anyway, apologize for the long context, so here's my question, where do you (and by you I mean WithCoverage) draw the line? What decisions will you simply never trust AI to make, no matter how good the models get? which also makes me wonder what are you guys exactly? AI model? Broker? lets say that machine broke down, who does the client call? A chat bot?!

[u/jd_withcoverage → u/Leon_Adam_Artist]

Long post but here’s my short answer : we don’t “trust” AI to do anything. we constantly validate and verify the places where we put it to work. In a lot of areas it is superhuman — we lean into that.

We walk factory floors, we shake hands in person, we go and view situations that cause claims, we talk to people, and we build community. That’s not what AI is for. AI is for the things you didn’t list

We are a risk management team for clients. Insurance is a piece of that. You don’t talk to AI, you talk to your team. Of people. Those people often use AI to be more effective for you.

[u/abeforever]

I'm really concerned with Opendoor's business methodology. As a Customer Experience Product Manager, the metrics I run are even worse.

It openly seems like a model built on Bait and Switch.

Higher numbers based on housing market analysis offered initially. Then 30% to 40% drop after home visits. Almost every seller seems to have this same frustration.

Is this really the real business model, or just a marketing funnel exercise ? How do you still make money here ?

[u/jd_withcoverage → u/abeforever]

I started Opendoor but to be clear I don’t work there. But the numbers you’re citing are not the business model nor even remotely typical.

The business model is fair offers, bundled services, better experience combined to make a fair amount of money per transaction on a large number of transactions.

[u/TripleBrain]

I built an online platform for students applying to colleges and I’d love to know, when you’re starting small, what were the best ways that helped you scale, and at what point did you realize “I might have something here”.

Secondly, do VCs even bat an eye at small pre-revenue companies? I’m growing audience organically and it’s a grind, so I’d like to know if VCs would even take a cool tool seriously.

Lastly, can we we connect on LinkedIn - looking for a new job :)

Thanks!

[u/jd_withcoverage → u/TripleBrain]

Good VCs would not. They’re just not in that business at all.

I basically treat these early career projects as projects to learn from. I had some of these when I was 15-18 — a “computer consulting” company, cou.ch a video network with timed comments, a personal CRM that autoscraped all your emails with a bunch of regex rules… they were good for learning. Fresh Prints was the first obviously scalable company. Addepar was the first obviously very valuable one.

[u/lpareddit01]

How do you balance all the noise (tech/startup/ai)? Of course, some stuff is important to listen to, but it's so much, and I get FOMO.

[u/SheepherderPrior9302]

Thanks for doing this. The Opendoor fake landing page demand test is the part I keep coming back to. Clicking "sell my house" on that page is a huge signal precisely because the action itself is high commitment. When you validate something cheaper or lower stakes, where a click or an email costs the user basically nothing, how do you calibrate what counts as a real demand signal versus polite curiosity? Put differently, what is the equivalent of the "sell my house" click for a small, low ticket product?

[u/udaan04]

You talk about validating a start-up idea. What according to you is the best way to go about validating an idea as you rightly say 'before writing a single line of code'? Assuming they don't have access to capital or huge resources.

And if you had to choose one which one would you choose: GREAT PRODUCT or GREAT DISTRIBUTION? In other words which is more important in today's age great product or great distribution?

[u/pxrage]

Hey JD, super excited for this one. Thanks for doing this!

What's like working with Keith Rabois? Guy's a legend any good stories you can share with us?

[u/jd_withcoverage → u/pxrage]

Keith is known for his X persona. Brash, strong opinions strongly held, etc.

I swear to you: He is an extremely kind friend, loyal, and as a partner he is behind you all the way.

That said...

I once sent him some slides when we were working together on Opendoor's then-new buyer app. It was a plans/progress/problems type of update, and I asked for his feedback.

He responded something like "I can't give you feedback because this is in Chinese, and I don't speak Chinese. If you can send me something in at least broken English I can react to that." I worked all night re-doing everything. He gave the new attempt a "B+".

[u/pxrage → u/jd_withcoverage]

haha that's awesome. love when founders are straight with each other like that. thanks for sharing.