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Angel Investing, Growth Tactics, and eComm Stacks with James Beshara

Angel Investing, Growth Tactics, and eComm Stacks with James Beshara

Adrian Alfieri
Adrian Alfieri
CEO, Verbatim

James Beshara is a repeat founder, angel investor, podcaster, and prolific writer. His latest venture, Magic Mind, offers a DTC energy shot fueling flow-states and productivity around the world, while his podcast, Below the Line, uncovers all aspects of the founder's journey with over 100K listeners.

What’s perhaps most impressive is his angel portfolio, which spans checks into high-growth companies like Mercury, Haus, Gusto, Clubhouse, Bolt, ThirdLove, and Recess. We sat down with James to learn from his diverse experiences, including discussing why infrastructure is the best wave to ride as an investor, what trends are actively shifting in the eComm landscape, and to discuss his early hurdles at Magic Mind.


Pre-Launch Jitters and Iterative Rollouts

In terms of advice he’s learned the hard way and would pass on to a pre-launch DTC startup, James recommends having a thorough understanding, from day one, of the cash flow and inventory needs, as well as broader operational and accounting structures, of your business.

As James describes it, he entered entrepreneurship with a software-first mindset and spent the first 9 months of running his DTC brand virtually in the dark on the deeper financial and inventory cash flow topics before he brought on a strong financial consultant and advisor.

In retrospect, he recalls that his early lack of knowledge, and thinking the accounting of a physical goods business would be “pretty straightforward” was a risky and expensive move that could’ve easily gone south.

Once you are over a few thousand dollars of sales, back-of-the-envelope math no longer works. You need a detailed understanding of your inventory costs, labor costs, shipping, returns, acquisition channels, etc. along with both fluctuations and optimizations of each to truly understand what the business can look like if you’re fortunate enough to grow it rapidly.

Finding a great DTC financial consultant, often called an FP&A consultant (not an accountant), was invaluable to move from a flashlight to a floodlight on the cash flow of the business.

He also adds that many founders get caught between wanting to launch their MVP as quickly as possible and dragging their feet until they’ve completely fulfilled their vision for the product. It’s a fine balance, and most founders err on the side of caution.

But as James puts it, there are multiple launches in any company’s lifecycle. For instance, Airbnb — which acquired his last startup — and Magic Mind had three separate launches. With each iteration, both concepts became more fleshed out and radically improved their offerings. In his mind, you can (and should) launch multiple times, with the first being for friends and family and as early as possible.

Finally, James drives home the point that it’s critical to make peace with the fact that everything in the startup world takes twice as long and is three times as expensive as you’d expect.


Growth Advice: The Solution is the Product

To boost DTC conversion of one-time users into subscribers, James maintains one rule of thumb: the answer begins and ends with the inherent quality of your product.

If there’s exceptional product-market fit and the product quality itself is undeniable, a strong percentage of customers should be able to sample it just once and be convinced that it’s worth a repeat purchase. “The first or second version doesn’t need to hit a 60% repeat purchase rate, but when you are ready to go all in, it does,” James says of most DTC consumer products.

The key is establishing that positive first touchpoint and then following up with the opportunity to subscribe with a seamless signup flow. In a heavily inundated market, it’s too difficult and too expensive to peddle your product to a customer, who’s already overwhelmed by their options, if they don’t truly love it.

Rather, it’s far more efficient to get back to product fundamentals.

In James’ words, invest the time upfront to ensure your product quality won’t miss, then watch the repeat buyers roll in — with no intensive marketing spend required on your end. It is either a heavy lift upfront or heavier and heavier less on the backend. So it is far more efficient to take the time upfront to ensure that people truly love your offering.

“To put it bluntly, getting someone to subscribe to a high-quality product requires a fraction of the effort it takes to sell an average or mediocre product over and over.”


Tooling Stacks: A Decade-Long eComm Boom

James has watched the commerce ecosystem explode over the last decade, with one notable shift being the evolution of the eComm tooling stack. For instance, Magic Mind has an annual revenue run rate of north of $4 million yet employs only one full-time employee.

This is made possible by the 30+ tools, services, and partners like Tydo and Skio that James leverages.

He adds that the eComm stack is wildly more sophisticated and scalable when compared to the problem solving of ten years ago, which would’ve entailed throwing more and more workers at an issue to come up with a far less elegant solution. Put simply, more capital for less return.

On the flip side, while the eComm ecosystem has seen rapid improvements in products and tools within the last five years, James notes that subscriptions payment architecture has stagnated. Virtually none of the dominant tools on the market have been updated in half a decade.

“Despite a decade of progress in eComm, there are so many issues to be resolved on the subscription side of things. Luckily, Skio is tackling this space head-on.”


Placing Bets in the Enablement Ecosystem

On the DTC investment front, James is particularly impressed by the new normal of lower financial barriers to entry. In his words, you need far less capital than ever before (think under ten grand) to build a great initial product and launch it into the market.

Angel investors are also quickly becoming larger and larger players in fundraising, as opposed to old school venture funds which are warier of DTC than they were about a decade back.

Regarding niches he’s tracking from an angel lens, James continues to cut checks around the future of the eComm enablement landscape, particularly because investors can play a more foundational role in the massive wave unfolding, rather than simply betting on brands alone.

Charting a singular path to your customer as a lone DTC founder is incredibly difficult today, primarily due to the fact that so much of the infrastructure simply doesn’t exist yet. As the solutions to these growth bottlenecks are unlocked, James is prepared to climb aboard.

“Investing has been a 10-year journey for me, with each investment bringing a fresh opportunity to refine the art of it. All of them have either put a product into the world that I’m extremely proud of or helped me learn that much more for the next idea or founder to encourage further.”

Adrian Alfieri
Adrian Alfieri
CEO, Verbatim
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How it works (for brands)

Swipe to launch AI-generated ads

Brainstorming 100 unique, 40-second scripts is painful.

Manually matching 20 clips (from your 10,000-video library) to each shot in your 100 unique scripts is even more painful.

Creating 10 permutations of each of the 100 ads (for A/B testing) is maximum pain.

This writing is getting very long, but imagine voiceovers, captions, music, & manually uploading all 1,000 ads to Meta & TikTok on top of this.

Icon solves this with Adswiper: all you have to do is swipe right or left on AI-generated ads.

Adswiper handles scriptwriting, script-to-shot matching (using existing videos from Google Drive + AI-generated videos), permutations, voiceovers, captions, music, & more.

Swiping right will also automatically create ready-to-launch adsets across all channels (Meta, TikTok).

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Connect your video library (Google Drive, Dropbox, Air) & ad accounts (Meta, TikTok).

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What they're saying

Backbone
"Manual ad creation was limiting our testing potential. Icon's swipe system lets us scale to thousands of variants without the production headache."
Maneet Khaira

Maneet Khaira

CEO, Backbone

Products

Adswiper

Replaces CapCut ($7.99/month), Adobe Premiere ($54.99/month)

Swipe right or left on AI-generated ads made from videos in your Creative Library.

Uses AI for scriptwriting, script-to-shot matching, permutations, voiceovers, captions, music, & more.

Adswiper
Autopilot

Replaces Ad Managers (direct use)

Swipe to launch AI-generated ads automatically on all channels (Meta, TikTok).

Autopilot
Adspy

Replaces Foreplay ($49-$99/month + $20/user), AdSpy ($149/month)

Use winning ads from top brands to inspire AI-generated ads in Adswiper.

Adspy
Creative Library

Replaces Recharm ($500-3K/month), Air ($250-$2K/month)

Store, tag, create, & split videos with AI.

Creative Library
Creative Analytics

Replaces Motion ($1K-$10K/month)

See which ads are winning to inform AI-generated ads in Adswiper.

Creative Analytics
UGC

Replaces Billo ($99/video)

Get AI-generated UGC videos for your Creative Library.

UGC

Story

Kennan Davison

Kennan Davison

CEO, Founder
Kennan Davison
Kennan Davison
Kennan Davison
Kennan Davison
Kennan Davison
Kennan Davison
Kennan Davison
CPO, Chairman, Founder at Skio (CEO 2021-2024, $10M+ ARR in 3 years, profitable).
Previously: Pinterest, Hulu, Wieden+Kennedy (ad agency), League of Legends Challenger (Top 200 North America, 100M+ players globally), Y Combinator S20 (solo founder), Columbia (transfer, dropout).
Hi there, I'm Kennan!
Growing up, my dream was to be a pro gamer: this felt within reach in high school once I ranked top 200 North America in League of Legends (out of 100M+ players globally).
Despite this, I needed to support myself so I went to college and started learning to code. Coding came naturally (especially with 100 hour weeks) and I was soon skipping class to work at places like Hulu and Wieden+Kennedy (ad agency). Realizing that being paid to work full-time (vs. paying to go to school) sounded quite nice, I dropped out after 1 year and joined Pinterest.
After Pinterest, I started a company called Skio which does subscription management software for brands on Shopify. In just 3 years, we've partnered with 1000+ brands (Liquid I.V., Milk Bar, Polaroid, Barstool, Unilever, KraveBeauty, Boba Tea Protein), reached $10M+ ARR (+profitable), and built an amazing team of 50.
With advancements in generative AI (video specifically), I saw an opportunity to help brands bring their stories to life exponentially faster and make marketing much better (hence Icon).
I love learning how we can help better. Feel free to reach out anytime at kennan@icon.me.
Founders Fund

Founders Fund

Icon Investor
Founders Fund
Founders Fund
Founders Fund
Founders Fund
Founders Fund
Founders Fund
Founders Fund
Peter Thiel's Founders Fund is a venture capital firm. Its partners have founded and funded companies including PayPal, Palantir, SpaceX, Anduril, Flexport, Airbnb and Stripe.
Ron Shah

Ron Shah

Icon Investor
Ron Shah
Ron Shah
Ron Shah
CEO, Co-founder at Obvi, Co-host at Chew On This, Managing Partner at Gaas for SaaS.
Roman Khan

Roman Khan

Icon Investor
Roman Khan
Roman Khan
Roman Khan
Roman Khan
Roman Khan
President, Founder at Peak21, CMO at Raycon, CMO at Know Beauty, CMO, Co-founder at Linjer, CMO at Nutrition Kitchen.
Kennan Davison

Kennan Davison

CEO, Founder
Kennan Davison
Kennan Davison
Kennan Davison
Kennan Davison
Kennan Davison
Kennan Davison
Kennan Davison
CPO, Chairman, Founder at Skio (CEO 2021-2024, $10M+ ARR in 3 years, profitable).
Previously: Pinterest, Hulu, Wieden+Kennedy (ad agency), League of Legends Challenger (Top 200 North America, 100M+ players globally), Y Combinator S20 (solo founder), Columbia (transfer, dropout).
Yunyu Lin

Yunyu Lin

Founding Board Member
Yunyu Lin
Yunyu Lin
Yunyu Lin
Yunyu Lin
Yunyu Lin
Yunyu Lin
Head of AI at Ramp.
Previously: CEO, Co-founder at Cohere (acquired by Ramp), Nuro, Facebook, Y Combinator S20, Duke (dropout).
Kevin Jin

Kevin Jin

Engineering
Kevin Jin
Kevin Jin
Kevin Jin
Kevin Jin
Kevin Jin
Kevin Jin
Kevin Jin
Kevin Jin
Kevin Jin
Kevin Jin
Previously: CTO at Kalder, Compound Labs, Robinhood, Rippling, Impira, Flexport, Google, Tesla, TSM, Vanderbilt.

Why us

Track record of things that can't be faked

Icon is the best team helping brands get winning ads with AI.

Our CEO/Founder (who is writing this, sorry for writing in 3rd person) brings experience from Skio, Pinterest, Hulu, Wieden+Kennedy (ad agency), League of Legends (Top 200 North America, 100M+ players globally), & Y Combinator S20 (solo founder).

At Skio (subscription management software for brands on Shopify), he was CEO/Founder of the company from 2021 to 2024 helping grow revenue from $0 to $10M+ ARR in 3 years (w/ 90% margins) and a team of 50 (on $8.4M raised). Skio is profitable and still growing >100% YoY.

Our tech investors include Peter Thiel's Founders Fund, Kevin Hartz (A*, Eventbrite), Max Altman (Saga), Alex Botez (Chess), as well as founders & executives of OpenAI, Ramp, Flexport, Pika, Karat, & Cognition.

Our D2C investors include Ron Shah & Ash Melvani (Obvi), Roman Khan, Nick Shackelford, Jimmy Kim (Sendlane), Kevin Lee (Immi), Justin Mares (Kettle & Fire), Steph Liu (Levitate), Sara Du (Alloy), Jason Wong, as well as founders of Eight Sleep, Yotpo, Siena AI, Replo, Novel, Parker, GR0, DCL Logistics, Aftersell, Platter, Openborder, Prescient AI, Daasity, & more.

Our team has also worked with 1000+ brands like Liquid I.V., Milk Bar, Polaroid, Barstool, Unilever, Bulletproof, 100 Thieves, Vega, KOS, KITSCH, True Botanicals, mindbodygreen, Transparent Labs, GHOST, Wild One, OpenStore, The Nue Co., Immi, DRMTLGY, Boba Tea Protein, KraveBeauty, Glamnetic, Doe Lashes, Magic Mind, Remedy Organics, & Siete Foods.

Focused on helping brands get winning ads

Icon is focused on helping brands get winning ads vs. also juggling the underlying AI tech.

We believe our approach is fundamentally better because we're free to choose the best technology partner for a specific job.

To illustrate this, maybe one AI-video partner specializes in face closeups while another partner specializes in body movements (where face doesn't matter as much).

If we built all underlying technology in-house, it would create a fundamental conflict of interest where we can't offer a competitor's tool (that might be better) without losing revenue.

Products
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Other options

Adswiper (replaces CapCut, Adobe Premiere)
Replaces CapCut ($7.99/month), Adobe Premiere ($54.99/month)
Swipe right or left on AI-generated ads made from videos in your Creative Library.
check
x
Autopilot (replaces Ad Managers)
Replaces Ad Managers (direct use)
Swipe to launch AI-generated ads automatically on all channels (Meta, TikTok).
check
x
Adspy (replaces Foreplay, AdSpy)
Replaces Foreplay ($49-$99/month + $20/user), AdSpy ($149/month)
Use winning ads from top brands to inspire AI-generated ads in Adswiper.
check
x
Creative Library (replaces Recharm, Air)
Replaces Recharm ($500-3K/month), Air ($250-$2K/month)
Store, tag, get, & split videos with AI.
check
x
Creative Analytics (replaces Motion)
Replaces Motion ($1K-$10K/month)
See which ads are winning to inform AI-generated ads in Adswiper.
check
x
UGC (replaces Billo)
Replaces Billo ($99/video)
Get AI-generated UGC videos for your Creative Library.
check
x

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