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