Built & sold 8 DTC/SaaS companies. Pioneered the ecommerce aggregator model. Host the @acquanon podcast. Acquiring and investing in CPG, pet, and ecom brands.

Charlotte, NC
Joined July 2007
This irrigation company 6X'd monthly invoices after a 2025 recap. But the seller is already walking away before capturing the upside. Is labor constraint the real reason? Or is there more to the story? @BillDA and @endresenheather dig in. Listen now ⬇️
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This shipping business does big numbers, but there's a mystery: 6,500 fully paid for cassettes, sitting empty in a warehouse. Is it just the bottom of a cyclical shipping market? Is there a new competitor, or better tech out there? Or a bigger decline that doesn't come through on the listing? @girdley, @BillDA, @thegeneralmills, and @endresenheather dig in.
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Bill D'Alessandro retweeted
If you have to post AI slop, PLEASE use Chatgpt instead of Claude. Nothing more obvious or annoying on this site right now than this stupid ass "X sitting inside a Y, with a Z underneath."
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Bill D'Alessandro
@BillDAAug 24
This one time I was walking down the sidewalk in my neighborhood and a car stops. Rugged SUV. Guy hangs out the window. Square jaw, jacked. “Are you Bill D’Alessandro?” I’m pretty sure he’s a special forces operator sent to kill me. “Umm, yeah…” “I follow you on Twitter” Instead of killing me, he pulls over and we have a nice chat for 20 minutes right there. Turns out, it’s not a special forces operator. It’s @PEoperator 😁
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There is probably a similar test for home service companies, but for payroll. A: Rippling or some other software I don’t know because I’m not forward thinking enough B: Gusto, which is where I’m at C: ADP or Quickbooks Payroll…💀💀💀
Bill D'Alessandro
@BillDAAug 2
If you can ask only one question to assess a company’s culture - I have discovered the Rosetta Stone. “What expense report software do you use?” A) Ramp - willing to embrace new things, best idea wins, move fast and try things B) Expensify - we were (A) five years ago but now change feels scary C) Concur - 💀 (just wait until you try to use our ERP) D) Anything else - we are too clever by half and prone to side quests
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The rise and fall of wokeness: DEI commitments in corporate securities disclosures filed with the SEC. To me this seems a trailing indicator; most other measures of wokeness take off well before 2019 and peak in 2020 or 2021. But the shape! That's what a moral fashion looks like.
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If I was forced to make $100K/month with ecom in 30 days starting from zero, here's exactly what I would do in 20 steps: Days 1-3: Pick the right category and build the foundation Find a category where the buying decision has a strong trust component — supplements, kids products, beauty, pet, health-adjacent Validate the market size before touching anything — minimum $500M+ addressable market Find a white label manufacturer — target 80% gross margins before spending $1 on marketing Build a 100% subscription offer — no one time purchases ever Price at premium from day one — $10 signals $10 quality. Never apologize for your price. Days 4-7: Build the product and brand Design packaging that makes customers want to display it proudly — your packaging is your #1 silent salesperson Build a simple DTC website — no Amazon, no retail, own the customer relationship completely Offer 50% off month one — this is the highest converting offer structure I have ever tested across two 9-figure businesses Write 5 core educational pieces about what is wrong with your category — education builds trust faster than any ad Days 8-15: Launch influencer machine Find 25 micro influencers in your category — mommy bloggers if kids, health creators if wellness Pay flat fees — expect only 10% to convert, kill the other 90% fast Give them guardrails on what they can and cannot claim — then let them speak in their own voice Track every post — views, clicks, sales, hold rate. The market is voting every day. Your job is to listen. Whitelist the 2-3 winners immediately as paid ads from their handle — this is where the real leverage lives Days 16-30: Scale what is working Take winning influencer creative and run it as paid ads — 20-40% of budget behind whitelisted content Text every new subscriber personally within 24 hours — not a bot, a real human Let customers customize their order — it raises costs slightly but creates a moat billion dollar companies cannot replicate Survey every customer who churns — their reason is your next product improvement Pour everything behind the 1-2 channels converting — kill everything else immediately The conservative math: 25 influencers × 10% conversion rate = 2-3 winners 2-3 winners whitelisted as paid ads = dramatically lower CAC Lower CAC + 80% gross margins = profitable from month one Profitable from month one = no VC needed, ever $30/month subscription × 3,000 subscribers = $90,000 MRR At 200 new subscribers per day = $100K MRR in under 30 days That is the floor. One viral post can add 500 subscribers in 24 hours alone. I did this with $0 venture capital. $103M annual revenue. $260M exit. The playbook works. Comment "ECOM" and I'll send you the full breakdown. **must be following + retweet to receive. Every Wednesday at 3:30PM EST I host a free 30 minute open call where anyone can ask me anything about ecom, business, or building from scratch. Link to register: zoom.us/webinar/register/WN_… Or interested in working with me 1-1 ? Here's the link to apply: form.typeform.com/to/VW7NZSq… Let me know if you need anything else :)
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Bill D'Alessandro retweeted
Real estate is a bad investment for entrepreneurs. Half of you just blocked me. Hear me out. When you start pulling money out of your eCom business, and you should, don't reflexively shove it into residential rentals. I'm not talking about commercial RE. Or if you're full-time RE specializing with deep expertise. I'm talking about the casual residential play, the 2 or 3 rentals on the side. It's not worth it. My good friend @billda had a rental house. He ran the numbers when he sold, 20% IRR over a couple of years. Bill normally DREAMS about 20% IRRs. If anyone was going to love a rental portfolio, it was him. He got rid of it. The 20% IRR was pretty low in actual dollars. And the tenant renting it was a pain. They called him once because she saw a spider on the front porch. I use to own a rental in Bozeman. Bought in 2015 and rented/held through COVID and the TV show Yellowstone, which sent prices to the moon. Even with crazy appreciation, returns were in line with an index fund over the same stretch. But with infinitely more hassle, zero liquidity, and no geographic diversification. It was in a top 5 market for the period in terms of appreciation. What do you think median returns looks like? I love the concept of hassle-adjusted returns. When comparing RE returns you have to consider turnovers, property managers (still have to manage them), illiquidity, late-night spider calls, capex, the tax complexity. In my experience, returns struggle to match basic indexes. And that's before the hassle factor is considered. I'm not saying don't buy real estate. A primary home you love is awesome. But it's consumption, not an investment unless you're cashing out and moving into a van. Or maybe you have a property or vacation home you rent to defer expenses. Great, enjoy it! All I'm saying is it shouldn't be a meaningful way you deploy cash outside your business. Photo: Hassle-adjusted returns include paying for and managing 2 new rental roofs in 12 months. Ask me how I know.
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“One of the last remaining moats is product.” Bill D’Alessandro (@BillDA), VP of Corporate Development at FoodScience: “The way AI is commoditizing marketing and operations… It’s got to be legitimately different, and it’s got to be protectable.” “Or your Amazon and your Meta feed fill up with clones.”
Bill D'Alessandro
@BillDAMay 4
This picture was taken after I had quit my job, taken out an SBA loan, and invested my life savings to buy a skincare company called Nurture My Body. I loaded all the inventory (creams, lotions, potions) into a rented truck to drive it from the sellers' home warehouse in Seattle to my garage in Denver ... in Feburary. She warned me as I drove away - "oh yeah, if it freezes it will be ruined" (!) If you're good at geography you've realized that I was about to drive over the Rocky Mountains in February with my life savings in a Penske truck ... that couldn't freeze. So every night I'd back the truck up to a motel and unload the inventory box by box into the motel room - stacking it floor to ceiling, leaving a path from the foot of the bed to the bathroom. Each morning I'd wait until it was warm enough, load everything back up, and continue the drive. I made it to Denver 3 days later, no damage! My holding company at the time was called Skyway Ventures, which morphed into Elements Brands. Nurture My Body became the cash flow foundation that we built 6 more acquisitions on, culminating in the acquisition of Natural Dog Company in 2018, which we then sold to Morgan Stanley in 2025. Today I'm celebrating my 14th anniversary of self-employment. It's been one heck of a wild ride. Here's to the next 14!
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“Debt isn’t bad. Debt is a tool.” “It’s like fire, you can cook your dinner or burn your house down.” Bill D’Alessandro (@BillDA) on the debt challenge in ecommerce over the past 5 years: “People [try to] fix a margin problem with debt. It’s that meme where the guy slaps a sticker on a tank, ‘fixed.’ Then they need another one. Then they go bankrupt.”
Replying to @youderian
Borrow wisely. @BillDA puts it best: debt is like fire. It can cook your dinner or burn your house down. Well utilized debt can help you grow. I also know numerous entrepreneur who took out large loans, didn't deploy them well and are in a really hard place.
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If you're digging apocalypse bunkers for the mega-rich... don't you want better than $635K cash flow? At least some danger pay against getting disappeared so nobody knows their floorplans? @girdley, @BillDA, and @endresenheather dig in.
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Bill D'Alessandro retweeted
Borrow wisely. @BillDA puts it best: debt is like fire. It can cook your dinner or burn your house down. Well utilized debt can help you grow. I also know numerous entrepreneur who took out large loans, didn't deploy them well and are in a really hard place.
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This business buries fiber inside railroad easements. 25-year niche. 4x earnings. So good we found a potential buyer DURING the episode. (And the listing's gone.) @girdley, @BillDA, and @endresenheather dig in.
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Charlotte is the most underrated city in the country and it’s not even close • Affordable • Nice people • Great weather • High paying jobs • Cool neighborhoods • Short drive to the beach or mountains
Murray Hill Guy
@MurrayHillGuy1Jun 3
Underrated city rankings: 1. Charlotte 2. Tampa 3. Pittsburgh 4. Cincinnati 5. Kansas City 6. Columbus 7. Richmond 8. Greenville 9. Indianapolis 10. Milwaukee Criteria: • Good jobs • Attractive people • Affordable enough • Can still get a reservation without knowing the owner
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A 30-year-old porta potty business in Madison, WI with 48% margins and zero marketing spend. But is this "recession-proof" business really worth $1.6M? @girdley, @BillDA, and @endresenheather dig into the poop economics. Listen now ⬇️
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i aspire to be able to write like this, wow.
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So you want to buy a Demolition business... listen to this. I spent 21 year in this business until regulation forced me out. I gave my best years to demolition, I loved it, BUT I built ZERO VALUE. In this episode you will hear about a 40 year old business that the hosts dont think will sell at 3x, most like likely will close down. It has $1mm in SDE after 40 years the seller has no value. It actually says his real estate is worth more than his business. Young entrepreneurs... buy or build a business with value, its the same amount of work.
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Before avocado toast, Airbnb side hustles, Barry’s boot camp, juice cleanses and running marathons, white people were doing silly things like this couple (my parents) who adopted two Korean kids in the 1980s in Kansas. While we didn’t turn out to be the passive income hack they hoped for (2 decades of massive cash burn w no return), they have received unconditional love from me and my sister and 4 loving grandchildren. I’ll always be grateful to be in America no matter what. Found this picture of the day I was picked up at the airport at age 3 in Kansas city while home this Thanksgiving.
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Brivael Le Pogam
@brivaelApr 29
Elon Musk avait dit un truc qui m'avait marqué sur l'allocation de ressources. En substance : passé un certain niveau de richesse, l'argent n'est plus de la consommation, c'est de l'allocation de capital. Cette phrase change tout. L'économie, dans le fond, c'est juste un problème d'allocation. Tu as des ressources finies et des usages infinis. Qui décide où va quoi ? Imagine une cour de récré. 100 enfants, des paquets de cartes Pokémon distribués au hasard. Tu laisses faire. Très vite, un ordre émerge. Les bons joueurs accumulent les cartes rares, les collectionneurs trient, les négociateurs trouvent des deals. Personne n'a planifié. Et pourtant chaque carte finit dans les mains de celui qui en tire le plus de valeur. Le système maximise le bonheur total de la cour. C'est ça, la main invisible. Maintenant fais entrer la maîtresse. Elle trouve ça injuste. Léo a 50 cartes, Tom en a 3. Elle confisque, redistribue, impose l'égalité. Trois effets immédiats. Les bons joueurs arrêtent de jouer, à quoi bon. Les mauvais n'ont plus de raison de progresser, ils auront leur part. Les échanges s'effondrent. La cour est égale, et morte. Elle a maximisé l'égalité, elle a détruit le bonheur. Le problème de la maîtresse, c'est qu'elle ne peut pas avoir l'information que la cour avait collectivement. C'est le problème du calcul économique de Mises, formulé en 1920. L'URSS a essayé de le résoudre pendant 70 ans avec le Gosplan. Résultat : pénuries, queues, effondrement. Pas parce que les Soviétiques étaient bêtes, parce que le problème est mathématiquement insoluble en mode centralisé. Quand Musk a 200 milliards, il ne les consomme pas, il les alloue. SpaceX, Starlink, Neuralink, xAI. Chaque dollar est un pari sur le futur. Et lui a un track record. PayPal, Tesla, SpaceX. Il a démontré qu'il sait identifier des problèmes immenses et y allouer des ressources avec un rendement spectaculaire. L'État aussi a un track record. Hôpitaux qui s'effondrent, éducation qui décline, dette qui explose, services publics qui se dégradent malgré des budgets en hausse constante. Le marché identifie les bons allocateurs, la politique identifie les bons communicants. Le profit n'est pas une finalité, c'est un signal. Il dit : tu as alloué des ressources rares vers un usage que les gens valorisent suffisamment pour payer. Plus le profit est gros, plus la création de valeur est grande. Quand Starlink est rentable, ça veut dire que des millions de gens dans des zones rurales ont enfin internet. Quand un ministère est en déficit, ça veut dire qu'il consomme plus qu'il ne produit. L'un crée, l'autre détruit, et on appelle ça redistribution. Dans nos sociétés il y a deux catégories d'acteurs. Les entrepreneurs et les bureaucrates. L'entrepreneur prend un risque personnel pour identifier un problème, mobiliser des ressources, créer une solution. S'il se trompe il perd. S'il a raison, ses clients gagnent, ses employés gagnent, ses fournisseurs gagnent, l'État collecte des impôts. Il est la cellule de base du progrès humain. Le bureaucrate ne prend aucun risque personnel. Son salaire est garanti. Au mieux il maintient une rente existante. Au pire il la détruit par excès de réglementation, mauvaise allocation forcée, incitations perverses qui découragent ceux qui produisent. Mais dans aucun cas il ne crée. Regarde les 50 dernières années. iPhone, internet civil, SpaceX, Tesla, Google, Amazon, Stripe, mRNA, ChatGPT. Toutes des inventions privées, portées par des entrepreneurs, financées par du capital risque. Pas un seul ministère n'a inventé quoi que ce soit qui ait changé ta vie au quotidien. La France est devenue le laboratoire mondial de la dérive bureaucratique. 57% du PIB en dépenses publiques, record absolu. Une administration tentaculaire, une fiscalité qui pénalise la création de richesse. Résultat : décrochage face aux États-Unis, à l'Allemagne, à la Suisse. Fuite des cerveaux. Désindustrialisation. Dette qui explose. Et le pire c'est que la mauvaise allocation s'auto-renforce. Plus l'État prélève, moins les entrepreneurs créent. Moins ils créent, moins il y a de base fiscale. Plus l'État s'endette et taxe. Boucle de rétroaction négative parfaite. La maîtresse pense qu'elle aide, et chaque année la cour produit moins. Dans nos sociétés, ce sont les entrepreneurs, toujours, qui font avancer la civilisation. Les bureaucrates au mieux maintiennent une rente, au pire la détruisent. Aucune société n'a jamais progressé en taxant ses créateurs pour subventionner ses gestionnaires. La question n'est jamais qui a combien. C'est qui alloue le mieux la prochaine unité de ressource pour maximiser le futur de l'humanité. La réponse depuis 200 ans n'a jamais changé. Ce ne sont pas les fonctionnaires.
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Bill D'Alessandro retweeted
Adopting Claude speak in my regular life, episode 1: Partner: Did you do the dishes tonight? Me: Yes they're done. Partner: Why are they still dirty? Me: You're right to push back. I didn't actually do them.
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