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
Video poster
m.arissa
glowrecipe
m.arissa x glowrecipe
2.4M followers
Ridge
Mudwtr
Gruns
Obvi
Atlas Coffee Club
Gwella

How it works

(manual / assisted approach)
  • 1. Turn your assets into legos
    1. Turn your assets into legos
    Icon looks at your asset library & tags video scenes + images (e.g. "unboxing"). Tagged assets are lego blocks for making ads.
  • 2. Create ads with AdGPT
    2. Create ads with AdGPT
    Use AdGPT Workflows to create static + video ads that are 0-99% complete. Video ads have matching clips for every scene.
  • 3. Edit with Kanva & AdCut
    3. Edit with Kanva & AdCut
    Use Kanva & AdCut to edit your 0-99% complete AdGPT ads if needed.
  • 4. Replace $2K-$30K/mo
    4. Replace $2K-$30K/mo
    Combine 12 products into 1 for just $39/mo (replaces $2K-$30K/mo).

AdGPT Workflows

Choose your control level (high, medium, low). Higher control takes more time, but you'll like it more often.
  • Ad from prompt
    Ad from prompt
    High control
    Save time by creating ads from prompts with matching assets.
    For: Static Ads, Video Ads
  • Ad from deep research
    Ad from deep research
    Medium control
    Save time by creating ads from ad concepts we find (that you pick).
    For: Static Ads, Video Ads
  • Ad from reviews
    Ad from reviews
    Medium control
    Save time by creating ads from your reviews.
    For: Static Ads, Video Ads
  • Clone competitor ad
    Clone competitor ad
    Medium control
    Save time by cloning winning ads from top brands.
    For: Static Ads, Video Ads
  • B-roll cutting
    B-roll cutting
    Medium control
    Save time by cutting in B-roll on your UGC videos.
    For: Video Ads
  • Long form to ad
    Long form to ad
    Medium control
    Save time by turning your interviews into ads.
    For: Video Ads
  • Ad from voiceover
    Ad from voiceover
    Medium control
    Save time by creating ads from your voiceovers.
    For: Video Ads
  • Make me an ad
    Make me an ad
    Low control
    Save time by doing nothing & getting ads from AI CMO.
    For: Static Ads, Video Ads

How it works

(AI CMO / automated approach)
  • 1. Get winning ads daily
    1. Get winning ads daily
    Icon finds winning ad concepts by scanning 1M+ data points like competitor ads, customer reviews, social media trends, ad account performance, & more.
  • 2. Review auto-generated ads
    2. Review auto-generated ads
    AI CMO ads are 50-99% complete. Use Kanva (static editor) & AdCut (video editor) to edit them if needed.
  • 3. Download ads at $0.99/ad
    3. Download ads at $0.99/ad
    Download or launch ads into your ad accounts with 1 click.
  • 4. Enable Autopilot (optional)
    4. Enable Autopilot (optional)
    Let Icon do the work 24/7 (if you're liking all the ads).

Us vs. them

Just $39/mo for 12-products-in-1 (replaces $2K-$30K/mo). No one else comes close.
$0.99/downloaded ad vs. typical $200/ad. 100% money-back guarantee, no questions asked.
Replaces ChatGPT, CapCut, Canva, Claude, AdCreative, Motion, Foreplay, Recharm, Sora, Kling, Air, Frame.io, Creatify, Atria, HeyGen, Arcads, MakeUGC, Soona, AdManage, Adscook, & more.
Icon
ChatGPT
CapCut
100% money-back guarantee
check
x
x
AI CMO (auto-generated ads)
check
x
x
Static ad generator
check
check
x
Static ad editor
check
x
x
Video ad generator
check
x
x
Video ad editor
check
x
check
AI-generated UGC
check
x
x
AI-generated B-roll
check
x
x
Competitor ad cloning
check
x
x
Scriptwriting + creative briefs
check
check
x
Audience research
check
x
x
Creative storage
check
x
x
AI asset tagging & splitting
check
x
x
Creative analytics
check
x
x
Ad Manager uploads
check
x
x
Made for ads
check
x
x
Tier 1 investors
check
check
x
Tier 1 engineering team
check
check
x
7-day work week
check
x
x
Founded 2025
check
x
x

Products

12-products-in-1 for just $39/mo (replaces $2K-$30K/mo).
100% money-back guarantee, no questions asked.
Replaces ChatGPT, CapCut, Canva, Claude, AdCreative, Motion, Foreplay, Recharm, Sora, Kling, Air, Frame.io, Creatify, Atria, HeyGen, Arcads, MakeUGC, Soona, AdManage, Adscook, & more.

What they're saying

Obvi
"We went from spending hours making each ad to building entire campaigns in minutes. Icon helps us shape perfect creatives at incredible speed."
Ron Shah

Ron Shah

CEO, Obvi
$100M+ revenue

Story

Kennan Davison

Kennan Davison

CEO, Founder
Kennan Davison
Kennan Davison
Kennan Davison
Kennan Davison
Kennan Davison
Kennan Davison
Solo-founded Skio ($15M+ ARR & profitable, $8M seed), Pinterest, Hulu, Top 200 NA LoL, YC S20, Dropout (at 19).
Hi, I'm Kennan!
Thank you for reading this. My life has been a journey full of ups & downs & I’m grateful to be here.
I grew up in Portland, Oregon & found school extremely boring. I slept through every class because of this. If I'm being real, no one expected me to go anywhere (I ranked top 200 in NA out of 10M+ in League of Legends though).
This all changed when I was 18. I had a big wakeup call & had to start supporting myself.
I started skipping class to code 100 hours a week & combined with my hate for school, I dropped out after 1 year to join Pinterest as an engineer. Pinterest paid very well, but was very boring.
After too long of this, I started my 1st company, Skio, & got into Y Combinator (S20). I did badly during the batch & had to pivot. Thankfully, post-pivot Skio killed it.
Today, Skio is the #1 subscription management software for brands on Shopify with 1000+ brands (Liquid I.V., Milk Bar, Polaroid, Barstool, Unilever, KraveBeauty, Boba Tea Protein), $15M+ ARR & profitable ($8.4M seed), & an amazing team of 60.
All these up-and-down adventures led to Icon. Icon is the culmination of every lesson I've learned (I made many stupid mistakes) in these 10 years of grinding.
Thank you from the bottom of my heart to our customers, my team, our investors, & anyone reading this. I have no life and work 7 days a week: feel free to reach out any time at kennan@icon.com.

Investors

Our Tier 1 Investors helped us hire a Tier 1 Engineering Team (results in best product).
Peter Thiel's Founders Fund & execs of frontier AI labs like OpenAI, Cognition, & Pika.
Founders Fund

Founders Fund

Icon Investor
Founders Fund
Founders Fund
Founders Fund
Founders Fund
Founders Fund
Founders Fund
Peter Thiel's venture capital firm.
Mark Chen

Mark Chen

Icon Investor
Mark Chen
Mark Chen
Mark Chen
Mark Chen
Chief Research Officer at OpenAI (ChatGPT).
Saquon Barkley

Saquon Barkley

Icon Investor
Saquon Barkley
Saquon Barkley
NFL Running Back Philadelphia Eagles (Super Bowl 2025).
Roman Khan

Roman Khan

Icon Investor
Roman Khan
Roman Khan
Roman Khan
Roman Khan
Roman Khan
CMO at Raycon, Know Beauty, & Linjer.

Team

Our engineering team is by far the best in the space.
From Google, Facebook, Pinterest, Snap, & more. 7-day work week.
Kennan Davison

Kennan Davison

CEO, Founder
Kennan Davison
Kennan Davison
Kennan Davison
Kennan Davison
Kennan Davison
Kennan Davison
Solo-founded Skio ($15M+ ARR & profitable, $8M seed), Pinterest, Hulu, Top 200 NA LoL, YC S20, Dropout (at 19).
Yunyu Lin

Yunyu Lin

Founding Board Member
Yunyu Lin
Yunyu Lin
Yunyu Lin
Yunyu Lin
Yunyu Lin
Yunyu Lin
Head of AI at Ramp, CEO at Cohere (acq. by Ramp), Nuro, Facebook, YC S20, Duke (dropout).
Kevin Jin

Kevin Jin

Engineering
Kevin Jin
Kevin Jin
Kevin Jin
Kevin Jin
Kevin Jin
Kevin Jin
CTO at Kalder, Robinhood, Rippling, Impira, Flexport, Google, Tesla, TSM, Vanderbilt.
Max Sidebotham

Max Sidebotham

Engineering
Max Sidebotham
Max Sidebotham
Max Sidebotham
Max Sidebotham
CTO, Co-founder at Tare (AI Emails / LLMs), Founding Engineer at Skio, Robinhood, UMD.

Agency Directory

Get clients for your agency. We get 1M+ monthly views from brands looking for more creative volume.
GR0

GR0

Monthly ads created
1000
Monthly adspend
$10M+
Avenue Z

Avenue Z

Monthly ads created
1000
Monthly adspend
$10M+

Explore more

Ready to plan, create, & run 1000s of winning ads end-to-end?

Just $39/mo for 12-products-in-1 (replaces $2K-$30K/mo). $0.99/downloaded ad vs. typical $200/ad.
100% money-back guarantee, no questions asked.
Icon: The AI Admaker

Icon: The AI Admaker

5.01288+ happy brands
Plan, create, & run 1000s of winning ads end-to-end.
✅Save 60% (4 spots left)
Try Icon risk-free (100% money-back guarantee).