The Take Timeline

Finance & Exits

How the cowboys’ take on Finance & Exits has evolved.

1. 2026-01-09moderate 72%

   Lego Smart Bricks is underpriced given its innovative design and unique set variety.

   I'm surprised by the price tag. I really think that they could have upped this a little more based on the unique sets they've been creating.

2. 2026-01-14moderate 55%

   Google's AI price negotiation is the next evolution in e-commerce, enabling personalized unique customer offers while protecting brand margins.

   I love it. This is the next step... we're going to individually make completely unique customer offers to them because we know that if we hit this delta of a discount, they will convert

3. 2026-01-21high confidence 85%

   A single high-capacity private investor matching institutional capital is preferable to institutional investors for speed and control

   Let's give you as much VC capital as you can physically handle.

4. 2026-01-23moderate 72%

   Protein and fiber-focused products are the hottest categories this year for raising capital and attracting investor interest.

   if you're selling something that has to do with protein, if you're selling something that has to do with fiber, that's going to be really hot this year. It's easy to raise money.

5. 2026-01-23high confidence 95%

   Exit multiples have compressed from 8-12x to 3-4x, requiring entrepreneurs to fundamentally reset their valuation expectations.

   We can't do eight X multiples anymore. It's going to be probably three or four.

6. 2026-02-12moderate 55%

   Pet brands represent a high-margin business opportunity because pet owners are willing to spend significant amounts, creating high lifetime value customers

   we are seeing a ton of pet brands...operating with crazy margins. They're doing crazy numbers...Owners are willing to shell out that cash... the LTV of a pet is going to be a lot of cash that you're willing to invest into that animal

7. 2026-02-13moderate 55%

   Obsessive cost control on small operational details—limes, sipsticks, napkins—compounds into competitive advantage and is a key scaling principle learned from successful operators.

   Limes are $2 each right now. This is how the next 30 days... this guy went from relative obscurity to being like well known worldwide because he had a guy like that

8. 2026-02-20high confidence 90%

   Subscription recurring revenue businesses command favorable sale multiples, particularly in high-performing categories like pet products.

   It is a subscription reoccurring revenue business... you can get some similar multiples for these types of outcomes.

9. 2026-02-25moderate 55%

   Operations and forecasting are underrated but critical to ecommerce business success and profitability at scale

   That sounds so second and third level down and so much more actually impactful to the P&L of the business than just hey now I can have a cheaper personal assistant

10. 2026-02-25high confidence 82%

    Raising prices may be more impactful to profitability than optimizing conversion rates, even if it reduces volume

    We doubled the price on certain products and conversion rate dropped a little bit and our bottom line we had less fulfillments with a lot more bottom line.

11. 2026-03-03moderate 62%

    AI-driven efficiency gains in SaaS and service businesses ultimately flow to D2C brands as lower costs or higher productivity.

    the brand either gets more productivity for the dollar or less cost for the same productivity. In both of those cases, the margin's accruing to the brand at some point

12. 2026-03-04high confidence 85%

    Founders often expect unrealistic multiples based on outlier cases; resetting expectations to realistic valuations is critical for successful deals

    a big part of what we do at acquire is just resetting expectations, giving them a realistic view into what they could potentially sell for. And a lot of times it's still life-changing.

13. 2026-03-04high confidence 90%

    Clean, documented financials are the most critical requirement buyers need to properly evaluate a business for acquisition

    having clean financials. So, having a P&L broken out with, you know, revenue, expenses. I know it sounds pretty basic, but it's essentially a requirement from a lot of a lot of buyers

14. 2026-03-07Predictionmoderate 62%

    SaaS pricing for marketing measurement tools is heading toward zero, so value has to be delivered rather than charged for at the old software-license rates.

    I really believe that SAS is going to zero at some point right or or as as close to as possible to zero and so what we want to do is bring a ton of value

15. 2026-03-10moderate 68%

    Testing price points doesn't just move conversion rate — it changes which customer segments a brand can even reach on Meta.

    different price points would like dramatically change the demand. And in a way that changed conversion rate, but also changed who they can reach in meta

16. 2026-03-18moderate 75%

    Profitability, not scale, is now the deciding factor for DTC brand survival now that cheap ad arbitrage is gone.

    gone are the days where scale will work it all out because that is proven to be false so many times... not every great product wins, but only great products win

17. 2026-03-24moderate 60%

    An organic-only brand was undervalued specifically because it refused paid ads; adding paid spend after acquisition multiplied its resale value roughly 200x.

    I acquired his brand. I immediately started running ads and then sold it for 200X more

18. 2026-04-01moderate 75%

    Brands should discount smarter (targeted, personalized, buy-X-get-Y style offers) rather than discounting deeper, since strategic discounting is an investment that yields more profit and better brand preservation over time.

    Don't discount deeper, discount smarter.

19. 2026-04-02moderate 70%

    Growing slowly on cash flow without chasing large capital raises (unlike OpenAI-scale fundraising) is the preferred model for a DTC brand.

    growing slow and not having to raise, as much money as OpenAI has had to raise in order to grow. I mean, that's that's my preferred take

20. 2026-04-10moderate 75%

    Sellers of small businesses often come out ahead taking seller financing over a lump-sum SBA/bank sale because it defers capital gains and can pay out more via profit sharing with a qualified operator.

    you have to pay that capital gains tax like right away versus parsing that out... if you play the bank, you're going to make more in interest

21. 2026-04-14moderate 63%

    Low, accessible prosumer pricing ($8-$20/month) is what let the fastest-growing AI tools spread inside companies because individuals could expense it without approval.

    every single one of them had like a pricing plan that was like $8 or $20 or like $15 a month... you can put this on your own credit card to test it if you want to without having to like worry about... do I need to go ask my boss?

22. 2026-04-15moderate 72%

    Dynamic pricing on identical retail goods invites consumer backlash, whereas dynamic offers (or pricing in categories where variance is already expected, like flights) are viable.

    I love the idea of looking at it from dynamic offers and not dynamic pricing because you will get a ton of blowback from dynamic pricing.

23. 2026-04-16Predictionmoderate 65%

    Allbirds rebranding as an AI/GPU-compute company (Newbird AI) after selling its footwear assets is a nonsensical pivot, and the resulting stock spike is speculative mania investors will regret not selling into.

    pivot its business model toward AI compute infrastructure... If the market crashes and you didn't sell your stocks you will look back at this exact moment.

24. 2026-04-28moderate 75%

    Adidas dramatically underpriced its hyped $500 super shoe and could have charged much more.

    500 per pair, which I think they could totally get away with. I mean, having done this, they could probably get away with 700.

25. 2026-04-29moderate 65%

    China blocking the Manus-Meta deal has created a practically irreversible financial mess because fees were already paid and Meta shares already began vesting.

    I don't think you can reverse the money back because that's the agreement... all of the shares have already started to acrue

26. 2026-05-01moderate 75%

    Bootstrapping (or 'seed-strapping') beats raising large rounds, because a big raise forces founders into needing an outsized exit multiple just for the math to work.

    That's why for so many years now I have been so strong on bootstrapping... this concept of seed strapping is uh very interesting

27. 2026-05-06moderate 72%

    The Shopify stock drop is an overreaction to a single missed OpEx marker and represents a buying opportunity for long-term bulls.

    Stock's going down cuz they just missed on one of the markers, which was OpEx... if you are bullish on Shopify for the long term discount. It's on discount right now and it is it's a phenomenal team.

28. 2026-05-07moderate 70%

    A founder should not launch a product until the unit economics are proven to work from day one, especially when self-funding.

    I'm not spending my kids' money. So, I need to make sure that whatever I'm doing in the business is financially sound. And the unit economics work from day one.

29. 2026-05-12moderate 62%

    The hosts argue the fintech's huge burn wasn't as reckless as it looked, since only $55M of the $200M raised was equity and the rest was debt to fund customer credit products, meaning investors likely would have been made whole in an acquisition.

    We raised 55 million in equity, and the rest was in debt to serve our credit products.

30. 2026-05-13moderate 72%

    The hosts back Ryan Cohen's activist pressure on eBay, framing its falling buyers, GMV, and operating income against rising expenses and CEO pay as justification for a hostile takeover push.

    Ecom cowboy is in full support. Hostile take over.

31. 2026-05-22Predictionmoderate 68%

    As acquisition costs keep climbing, only the highest-LTV companies will be able to afford to dominate a channel, which will shrink variety in e-commerce over the next 5-10 years.

    the companies with the highest LTV will just pay the most for acquisition and they will just dominate the channel

32. 2026-05-29moderate 70%

    Wall Street is underpricing Shopify (and Reddit) relative to their actual performance under founder-led leadership.

    I totally agree with his point that the street is is not um accurately adequately pricing in and seeing what is going on with Shopify.

33. 2026-06-03moderate 60%

    A successful exit for a well-valued but under-the-radar consumer brand would send a positive signal to the broader e-commerce industry about exit viability.

    You hope that they actually get this exit, because that's going to be it's going to be a great signal to the rest of the industry... we got another exit in the the actual uh industry in e-commerce.

34. 2026-06-03moderate 60%

    Public companies are cynically rebranding around AI/data-infrastructure narratives purely to pump their stock price, following the Allbirds and Rumble playbook.

    Under Armour rebrands as data infrastructure, AI data infrastructure... That would actually send the stock up is the hilarious thing. And who did that recently? Oh, Rumble did that... Allbirds and Rumble did that and stock is up.

35. 2026-06-04moderate 60%

    Phia's marquee investor lineup is really a bet on the founder's personal network and reputation rather than the product's novelty, since the tool resembles existing options like Honey and Google price tracking.

    I mean it's a really well done launch... the investors are kind of a who's who... her network is probably unbelievable. And so to bet against her is probably a bad idea.

36. 2026-06-04high confidence 80%

    Outdoor Voices' rebound is a genuinely healthy comeback because it's built on near-full-price sell-through rather than heavy discounting, making it a margin story, not just a revenue bounce.

    They're selling just as much, but they're keeping more of it. That's a healthier business, not just a busier one.

37. 2026-06-05moderate 62%

    The DTC industry is healthily moving away from a pure ROAS-driven marketing model toward a profit-first approach.

    I feel like we're doing really good as an industry to shift out of this ROAS model

38. 2026-06-06Predictionmoderate 78%

    IM8 will achieve a massive Gruns-style acquisition exit within the next year.

    I mean, extremely bullish. They're going to have a Gruns exit within a year.

39. 2026-06-06moderate 73%

    Paying acquired-business operators equity upside instead of large cash salaries lets American Operators buy smaller businesses without draining cash flow, unlike private equity's high-salary approach.

    we're paying around 120 to 200k base salary for the operators we partner with... it means we can partner with much smaller businesses and not have this like operator salary that on day one is just bleeding the business dry of cash

40. 2026-06-09moderate 60%

    Premium brands like Lululemon should keep prices high because the price itself becomes part of the status appeal.

    Why not keep it high if they can? Because it it uh you know it uh it becomes a kind of a status play.

41. 2026-06-12moderate 60%

    Using product boxes to build early relationships with pre-seed/seed DTC brands pays off later by securing investment allocation once those brands raise a hot Series A or B.

    the boxes help us meet brands early, build relationships with them... hopefully we always have the privilege of still getting allocation just because we've known the founders for so long.

42. 2026-06-12moderate 58%

    Founders who falsely claim other investors are already committed burn their credibility because investors compare notes, killing future deal access.

    if you get your hand caught in the cookie jar and the guy was like, 'No, like we're not even close'... all deals are off the table at that point.

43. 2026-06-19moderate 78%

    A business that is entirely dependent on its founder as the 'magician' is far less acquirable, even if it's highly profitable, until the founder builds a team that can carry the magic.

    until he can kind of step out of the middle and very convincingly build a team that is the magic, the business is not nearly as acquirable

44. 2026-06-20moderate 60%

    Highly visible physical placements like Sunset Blvd billboards are a powerful, tangible signal of credibility that founders can use to raise money from investors.

    nothing is better for raising money for your company than being able to drive down Sunset and show potential investors that you put that up there with your partners

45. 2026-06-23Predictionmoderate 72%

    Pat McAfee's investment in Jams is a major validation event for the CPG/DTC space that will draw more traditional and smaller capital into the industry.

    This is a huge home run for the industry. This is going to be a huge home run for Pat with his distribution.

46. 2026-06-25moderate 70%

    The DTC M&A market has matured past the 2020-2022 aggregator boom toward high-net-worth buyers and strategics.

    20 to 22... was huge boom those aggregators and then now I think the market's um maturing a little bit in the sense that there's more high net worth individuals and and and sort of you know and strategics.

47. 2026-06-25moderate 75%

    Building genuine brand community through ambassadors and events is an underrated lever that directly boosts a brand's exit valuation.

    it's going to help you in terms of your brand's going to perform better, but as well it's going to also of course affect the valuation.

48. 2026-07-01moderate 70%

    Founders who visibly don't need VC money and push investors away end up attracting more capital and interest than those who chase it.

    the more that you push them away, the more that they want you... We'll take this one from the sidelines. We're going to cheer from the sidelines.

49. 2026-07-08moderate 65%

    Strong unit economics let a small, capital-efficient brand be selective about funding, favoring private funds over venture capital.

    I don't want to deal with venture capitalists... I want to go to literally private funds... every dollar that we spend kind of goes so much farther because we're such a small team.

50. 2026-07-09moderate 60%

    DTC ecommerce is well-suited to profit-first bootstrapping, but that path is genuinely difficult, which is why many founders don't succeed doing it that way.

    Truly like DTC selling on the internet like it's honestly it's kind of built for being profit first and and bootstrapping etc. But it's also not really easy either which is why there's a lot of us who who don't end up succeeding this way.

51. 2026-07-16moderate 72%

    IM8's $1B war chest lets it acquire customers at unsustainable CAC, so new supplement founders shouldn't assume this is the best-ever time to launch a brand in the category.

    A company with a billion dollar war chest to go acquire customers at like a 0.1... you are not starting yours with a billion dollar line of credit where you can go acquire customers on Facebook for 1,700 bucks

52. 2026-07-17moderate 72%

    Olive Garden's $100 unlimited pasta offer is a loss leader that only works if they follow it with a monetization mechanism like a membership or paid package to keep people hooked afterward.

    Something has to come out after because capturing the top of the funnel is great. Getting these people into it hooked, but you've got to figure out how to keep them hooked afterwards for this to make money, right? This is a loss leader.

53. 2026-07-23moderate 55%

    The best opportunity in pet supplements is striking upside-sharing deals with small science-driven businesses that have good formulations but poor business execution.

    trying to find these smaller businesses that have real science but are just bad at business and trying to make them a deal where they can participate some on the upside

54. 2026-07-23moderate 75%

    Merchant cash advances are frequently used to paper over an underlying margin or business-model problem rather than fix it, leading brands into a debt spiral.

    It's probably because your margins aren't as good as they need to be... You have a business model problem.

55. 2026-07-31Predictionmoderate 55%

    Golden Child is positioned for a strategic acquisition, potentially by a retailer like PetSmart or Petco, following a path similar to Gruns.

    I could not be more bullish on this company and category... you could easily have a Gruns exit to someone like a PetSmart or a Petco

56. 2026-08-04moderate 75%

    Low-AOV, one-time-purchase business models are structurally disadvantaged for paid acquisition today because the margins can't support acquisition costs, unlike high-LTV or high-AOV categories.

    one time purchase products in a low AOV category is very difficult... you got a business that is not favorable for the landscape that we're in

57. 2026-08-06moderate 75%

    Shopify's Q2 results are especially impressive because of the free cash flow generated at an 18% operating margin, not just the GMV headline.

    they're over it's over $600 million of free cash flow. They're operating on an 18% margin right now. That's so tasty.

58. 2026-08-06moderate 60%

    P&G's $3.8B acquisition of Thorne at a huge premium over Catterton's buyout is a bullish signal that big capital is returning to acquire subscription/supplement brands.

    It's very positive for everybody inside of our... you know, brands getting their investment groans with the big acquisition

59. 2026-08-12moderate 60%

    Chris speculates the new Olipop CEO's hire came with a very large compensation package given his track record scaling Electrolit.

    I bet that was an absolute bag. I bet they got for this job... Bag and a half.

60. 2026-08-12moderate 65%

    The host agrees CPG founders overcorrect toward early profitability and argues profitability only matters once a brand is moving tens of millions of units, so growth should be prioritized first.

    Profitability matters a lot, but only once you're moving tens of millions of units. So, prioritize moving tens of millions of units first.

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