Many founders establish businesses and only later realise they are hard to fund. Others aim to create “fundable businesses” yet lack the passion for a long journey. Somewhere along the spectrum is a happy medium which must be balanced along the growth curve as phases change and different types of funders come and go. In this episode serial entrepreneur Dileep Thazhmon, fresh from raising a $180m C round navigates us through this territory and describes how the balance is always changing.

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Jeeves (tryjeeves.com) help businesses organise all employee expenses under one unified platform which includes flexible funding in multiple currencies. As their slogan says “built by entrepreneurs for entrepreneurs”.

They have over 3,000 clients in over 20 countries which is a phenomenal achievement given that the business only opened to its first customer in 2021 :-!

Topics discussed include:

• the renaissance happening in Miami and Florida as a whole as a centre for business
• crypto and Miami, no income taxes but what had Florida lacked in the past?
• Dileep’s business background
• the golden age of building new businesses
• engineering from round one with fund raising in mind versus passion businesses and balancing the two
• is there such a thing as A Good Business per se?
• investors want to invest in Big Ideas  in Big Markets with Big Outcomes
• not all businesses need the whole series of funding rounds
• need to have commitment that will last to a project
• Dileep’s 3-Ts model
  • Team
  • TAM – Total Addressable Market
  • Traction
• Team & TAM are what early investors, Angels et al are looking for in seed rounds
• By A and B Rounds Traction becomes increasingly important – you cannot keep selling ideas/people/market
• By C round and onwards you need to have built a really good business – not just as it were early promise and ideas
• pick spaces in which you can pivot as you will probably have to pivot
• categories of investor and the rounds they prefer
• we must not forget all the great smaller scale businesses – not every great business grows to huge scale
• build something you want to build – why this is essential for a long journey
• taking funding means you have to be offering the chance of a logarithmic shareprice growth – again not something all business ideas can/could/should generate
• types of CEO who are best at marketing each round – its rare to find one who goes the whole way from Seed to IPO and beyond
• managing the C-Suite team through the journey
• a company itself is like a living organism
• a big part of being a CEO is [with limited resources] knowing which part of the business to invest in and not invest in at different stages of the journey
• prioritisation for the phase is a real skill – you need to knock, as it were, different balls out of the park to succeed at each round/phase
• what is the one function you need to get right at each stage/round
• Dileep’s product metric
• speed and mobility are the most important early skill – retaining this as layers are added to the organogram
• how scaling is a very different phase from the “zero to one”
• managing the necessity to have folks from incumbents versus not becoming an incumbent
• living in the “grey area”
• a C-suite team as a pelleton, managing its competition as it speeds up
• changing nature of functions as the company grows
• the key hire Dileep found essential to Jeeves growth
• the characteristics to look for when recruiting C-Suite
• force-multipliers
• a long section on choosing  investors, managing investors, the type of relationship you need to have, how to create them and how things work in good and bad times…
• how this has worked for Dileep in Jeeves
• the need for specificity in what a CEO needs – something CEOs often fail at
• the impact of excess capital in the world
• the real nature of VC businesses – services business, reputation business
• what kind of VC ends up complaining to his colleagues about the investee company and what they did to create the “unexpected” problems
• Dileep’s thoughts and advice on CEO-ing companies in difficult economic times
• nuances beyond the obvious cut expenses, increase revenue
• what you need from the team
• issues around “default alive” companies for company, investor and founder
• Jeeves products and USPs
• broader business bank plans

And much much more

Share and enjoy!