After Raising $1 Billion For Previous Companies He Created The First Smart Accounting Software

Sasha Orloff built his first two companies at the same time. Now he’s helping other founders figure out the financial puzzle they face on the startup journey.

On the Dealmakers Show Orloff talked about when you should move forward with your business idea, optimizing your time, the number one thing for increasing your startup’s success, how to pitch when fundraising, and more.

Listen to the full podcast episode and review the transcript here.

When It Is Time To Pursue Your Startup Idea

Sash Orloff grew up in California’s Bay Area. As with many successful entrepreneurs he spent some time traveling and exploring the world, and gaining new perspectives. 

He studied in Europe and spent time living in Mexico, Honduras, Washington DC, New York, and San Diego. Experiences he says help you see bigger opportunities as an entrepreneur. As well as breaking out of the bubble that living in San Francisco can put you in. 

He still returned to the Bay Area. Where he says he loves the constant focus on tomorrow. Being in the middle of all the energy and excitement, the VCs and founders. Which gives you a feeling of possibility. 

Orloff also found an early talent for math. Especially applied math that he could use in real world business situations in his career across startups, non-profits, governments, mult-nationals across many industries

After 9/11, as many people were reevaluating their properties in life Sasha was inspired by a book about microfinance. That led him to work with the World Bank while getting his MBA, and then Citigroup’s venture capital team. Which brought him back to the West Coast of the US. His job there working with entrepreneurs and finding great ideas to fund inspired him to come up with his own.

Applying To Y Combinator

On a whim on the way to the airport, he applied to Y Combinator, and got in. The mobile financial services technology he built as a result of that ended up with him building and funding two companies at the same time, Mission Lane and LendUp.

When it comes to your own startup ideas Sasha points to three factors in the decision to make the leap. 

The first is being so obsessed with it, that you go out and tell everyone. You battle test it by getting their feedback, and having them tell you why it won’t work. 

Secondly, making sure you can pull together a great team. Being able to convince others to quit their jobs and work for little, in the hope you can build this thing into a success together. 

Then, thirdly, finding the path to finance it. For some that may be through bootstrapping. For others selling funds. Or others raising venture capital on the journey. 

When you can check those boxes, and you can’t think of a reason why all of those things don’t exist, it is the reason it should exist. In his own words he says “I can’t find a way to say no and I get so excited about the yes, I feel like I don’t have a choice. I have to do it.”

Exiting And Developing New Business Ideas

After his first two companies, working seven days a week, for eight years in a row, he decided he needed to take some time off. Those first two ventures found their product market fit quickly, became well capitalized, and they placed new CEOs in each. 

What was supposed to be a couple months off to decompress and spend time with his family, turned into almost a year break. 

For several months he left his mobile phone at home, practiced being present, and wrote down business ideas on a notepad. Big, ambitious ideas he thought that he was uniquely suited to tackle, Of course, there is also considering the size of the market and business you can build out of your idea, if it is defensible, how you will break into the market, and if people will pay for it 

After six months he began bouncing those ideas off of other founders, and VCs. Then boiled that list down from 100, to twenty, to five, to three, to the one.  

Sasha says that big trends and shifts also create the right timing to launch your ideas. Just as it was with 2008 and new financial regulations, the evolution of venture capital and startups for his third company, and the changes in markets and the economy happening now for other aspiring entrepreneurs. 

Pitching & Financing Your Company

Mission Lane raised around $675M. LendUp raised about $361M. His new venture Puzzle Financial raised $20M just to get started.

Storytelling is everything which is something that Sasha Orloff was able to master. Being able to capture the essence of what you are doing in 15 to 20 slides is the key. For a winning deck, take a look at the pitch deck template created by Silicon Valley legend, Peter Thiel (see it here) where the most critical slides are highlighted.

Remember to unlock the pitch deck template that is being used by founders around the world to raise millions below.

Orloff says that your two biggest resources for building a company are your people and your capital. 

He advises not to make the mistake of thinking you have to do everything yourself as an entrepreneur. Instead, hire smart, talented people, empower them to do their best work, and get out of their way. Your product will scale fast, and you’ll be able to scale yourself faster, and focus on your unique tasks, like setting a vision, hiring the team, and raising capital to pull it off. 

When you are fundraising and pitching you have to tell your story and make sure that aligns with your finances. You have to highlight the best parts of that story, in a compelling way, and avoid going too deep in detail. The problem pitching as a founder is you know too much, so creating an exciting, vision of what the future at the right level of detail is hard.

He advises to “get help early.” To get that first sentence right, get the story right, and the practice your pitch. 

Today, with Puzzle Financial, Sasha is empowering other founders to make better decisions, and understand their finances better with software, data, AI, and machine learning. 

Listen in to the full podcast episode to find out more, including: 

• Decision making and failing fast
• Hiring and empowering your team
• Debt versus equity financing
• How Puzzle Financial is empowering entrepreneurs at all levels

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