An Interview With Chad Silverstein
I’m still a big fan of “chatting with your thoughts”. Add all your personal docs, goals, one-pagers, anecdotes, strategies, riffs, random thoughts into a vector DB and then chat with it. “What was that amazing startup idea I had based on kitten videos?”. Oh yeah, I forgot about that one… AI’s “chat with your thoughts” capabilities is superior to basic search in my opinion.
In today’s tech-driven world, artificial intelligence has become a key enabler of business success. But the question remains — how can businesses effectively harness AI to address their unique challenges while staying true to ethical principles? To explore this topic further, we are interviewing Jared Yaman.
Jared Yaman is the CEO of Spresso, an AI-powered e-commerce solutions provider that offers advanced tools for pricing intelligence, commerce management, and spend analytics. Previously the Co-founder, COO, and Head of Software of Boxed, Jared led the company’s growth and innovation in the online wholesale retail space. Under his leadership, Spresso has secured funding from BlackRock, accelerating its global expansion and enabling businesses to optimize growth and profitability through data-driven strategies.
Thank you so much for joining us in this interview series. Before we dive into our discussion, our readers would love to “get to know you” a bit better. Can you share with us the backstory about what brought you to your specific career path in AI?
I graduated law school in 2008, and with such impeccable timing made it to New York ~48 hours before Lehman Brothers collapsed. Not being long for corporate law did however have its advantages. Despite the economic downturn there was a golden era of startups just beginning, even beyond the iPhone. My first company in tech was acquired by a Bay Area heavyweight and that’s where I really cut my teeth on tech and the VC world. Since then, whether it’s gaming or eCommerce, myself and my cofounders have been focused on delivering very innovative technology solutions to improve our customers daily lives.
You are a successful leader in the AI space. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?
As with many others in our field, persistence, curiosity and problem-solving come to mind. I co-founded a company that competed in retail against Walmart, Costco and Amazon. We were able to last 10 years, operate through the pandemic (selling toilet paper and sanitizers) and even IPO. Ultimately, we didn’t have a great outcome and had to wind-down the business. It takes persistence to come back for the next one. Because we’re in a fast-moving space you have to stay on top of everything. Consume content, follow thought leaders, visit conferences but stay disciplined not to chase shiny objects. No matter what, stay competitively curious. Lastly, I think problem-solving speaks for itself but if you’re building a business where problem-solving is straightforward I don’t think you have much of a business. To build something special you’ll be solving problems with well less than 100% certainty of the outcome.
Let’s jump to the primary focus of our interview. Can you share a specific example of how you or your organization used AI to solve a major business challenge? What was the problem, and how did AI help address it?
We use AI — our Pricing Agent — to manage pricing for our merchants. We don’t test pricing, we manage it across a range of opportunity. We implement our application and configure pricing campaigns. Whereas a typical merchant’s handbag may be listed at $100 our pricing management solution and instead creates a range of pricing. We then gather data at different generative price points (say, $85-$115 for the handbag) and dynamically allocate new customer traffic to the site to the profit maximizing price point. Slightly counterintuitive, but we’re benefitting both merchants and their customers as often the profit-maximizing price point is lower than the standard price.
What are some of the common misconceptions you’ve encountered about using AI in business? How do you address those misconceptions?
On the one hand there’s the general stubbornness of learning a new skill or modifying your routine and having to admit “there’s a better way” — by allowing AI to supplement your outputs and strategies. Supplement, not replace. And that’s the other hand — the thought that AI is here to replace us. Quite the opposite, our Pricing Agent is intended to execute and amplify the strategy of a merchandiser, not replace them. It’s just a learning curve. When I was younger I adopted the “Let me google that for you” troll. What’s the capital of Montana? Don’t ask me…just Google it! 20 years on, AI is the new “LMGTFY”.
In your opinion, what is the most significant way AI can make a positive impact on businesses today?
I think AI can actually improve our skills — IF we’re willing to challenge ourselves. If someone asks me “what is 17 x 14” I might pull out my calculator, mentally check out and peck away while juggling numerous distractions. But why not attempt mental maths “17 x 10 = 170…adding in 17 x 4 = 68… 68 + 170 = 238! Now let me verify in the calculator… 238. I challenged myself, and I got it right!” Why not do the same thing with AI? If I’m using it to flesh out a business plan or a proposal, what did I miss versus the AI output? Was it a stakeholder concern, ROI, competing interests, etc. I think it’s important to compare our baseline strategies to the AI outputs and ask ourselves “how could I have done better?” and add it to your toolkit. In my day, you had to walk uphill, in the snow, both ways to learn and now it’s right there — it’s a great time to be a learner.
Ok, let’s dive deeper. Based on your experience and research, can you please share “5 Ways AI Can Solve Complex Business Problems”? These can be strategies, insights, or tools that companies can use to make the most of AI in addressing their challenges. If possible, please share examples or stories for each.
- We’re a technology company and AI coding tools have been tremendous for increasing the coding output and delivery of our engineering team. They’re also extremely valuable for cross-training and expedited on-boarding to new projects.
- Efficiency and automation are key. Have to miss a meeting? Now you can get the AI summary, inclusive of tone, advice, text, and defined next steps.
- I’m still a big fan of “chatting with your thoughts”. Add all your personal docs, goals, one-pagers, anecdotes, strategies, riffs, random thoughts into a vector DB and then chat with it. “What was that amazing startup idea I had based on kitten videos?”. Oh yeah, I forgot about that one… AI’s “chat with your thoughts” capabilities is superior to basic search in my opinion.
- Creating a proposal. If you have a high-touch meeting and are looking to land that major deal, AI is a tremendous asset to amplify your pitch and prep for the inevitable back and forth. We run our proposals, strategies, pros/cons through AI before every major deal. Of course we make sure our humans own the comms layer and deal-closing.
- Data Normalization. For a lot of our partners data lives in different silos with different definitions. At the heart of what we do, we need clean, structured, normalized data. Do you live at 500 Main St. or 500 Main Street? AI has been a huge asset in cleaning our date inputs to allow our algorithms to perform to their fullest potential. If you care about data, we use AI to make-it-make-sense.
How can smaller businesses or startups, with limited budgets, begin to integrate AI into their operations effectively?
This is a very dynamic space. Many intelligent commentators tend to think “SAAS is dead” because there will be an AI agent for every need. However, at the same time, I’d advise against a bloated stack of tools: AI agent for my calendar, for my meetings, for my prospecting, for my CS chats, for my docs, etc. I think it’s best to consider a platform approach to your AI stack to ensure compliance, security, data privacy and preventing data leakage. This space will shake out in the next 24 months.
What advice would you give to business leaders who are hesitant to adopt AI because of fear, misconceptions, or lack of understanding?
It is still early days, but most of the kinks are getting ironed out by the day. I remember when people were hesitant to use their credit card to make payments on a mobile phone — but I think we’d all admit it’s worked out okay. I would recommend business leaders allocate that extra level of effort to look at their AI requirements holistically and consider the up and coming platforms that enable these AI tools while also ensuring security, data privacy, compliance and prevent bloating your P&L with 30+ disparate AI tools.
In your opinion, how will AI continue to shape the business world over the next 5–10 years? Are there any trends or emerging innovations you’re particularly excited about?
I would leave the “futurist” convos to the experts (if only we could engage some of our top Sci-Fi novelists of the last 75 years!) but would agree with those that AGI is imminent. Instead of responding based on the dataset it was trained on, AI will actually be able to learn and problem solve itself. There’s a seismic difference between “help me write a query to fetch yesterday’s sales” and “hey, figure out a way to create an app that sends a text every time my son isn’t home by 7pm. Oh, also publish it to the App Store.” I’m a big fan of the forward-thinking of the Terminator movie producers, they were so ahead of their time. In a 5–10 year window, there’s a lot of things on the table that we may not be ready for.
How do you think the use of AI to solve business problems influences relationships with customers, employees, and the broader community?
People are really smart and I think it’s important to make the currency of the future genuine interactions and authenticity. Humans are uniquely wired to zig when the conventional wisdom is zagging. As many of our connections become artificial we reflexively gravitate toward authenticity. This will be fascinating to watch. If every email you receive is written by AI, very quickly we’ll ignore the email channel altogether and favor inter-personal reactions. I think we’re seeing this already in the outbound sales space. It’s borderline mutually assured destruction, if AI dominates a channel, humans will change the channel, lemme grab my remote.
You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people through AI, what would that be? You never know what your idea can trigger. 🙂
Great influence is a stretch! I just want people to appreciate the amount of learning opportunity that’s at their fingertips. I wish I had YouTube, coding copilots, tutorials and AI assistants when I was a kid. When I read the prose of the greatest authors in our history I think it’s obvious that our generation lacks their verbal dexterity, wordplay and purple prose. We just can’t articulate the way they used to. I’m a victim of our microwave society of instant gratification but long for the ability to engage with a longform thoughtful conversation, a novel or thought piece that I just can’t put down. My recommendation is to find the ideal balance of thoughtfulness and the instant gratification, genius level outputs of AI.
How can our readers further follow you online?
We’re at Spresso.ai, and you can find me on LinkedIn or send a text to 734.223.0821.
This was great. Thank you so much for the time you spent sharing with us.
Jared Yaman of Spresso AI On How Artificial Intelligence Can Solve Business Problems was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.