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How being bootstrapped saved us

How a services business reset into a $1M SaaS pivot, and how $4.38M of debt was converted into 8.5% equity

Jonathan Fishbeck · EstateSpace

Published September 1, 2022
About this resource

Jonathan Fishbeck, CEO of Estatespace shares:

- What caused us to lose focus, almost fail

- How we converted $4.38M debt to 8.5% equity

- Why SaaS is the best thing on earth

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What you’ll learn

Jonathan Fishbeck explains why bootstrapping gave EstateSpace room to reset, solve a shared customer problem, and stay independent. He also discusses capital-gains considerations and the value of learning from a founder community.

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Key moments

Find the ideas you need and go straight to the source.

Identify the shared problem

“million in service revenue and at that time we realized that that's just not where we wanted to be so we had like a client we had a a shareholder and we also had an affiliate partner that uh that was that was really investing in us so we were able to actually convert all of that to equity to benefit the company save on taxes and really start to partner with our with our biggest client which was a 100 million dollar construction management firm out of New York um and so so now uh 2022 we're finally scaling they were able to help us kind”
Watch at 01:28

Use a business reset

“takes integration you know to start a conversation to solve a problem for what we were trying to solve for started at like sixty thousand dollars to talk to somebody another sixty thousand dollars to figure it out and maybe I needed an I.T team to run it and so our in our space we realized that SAS was going to be the thing that we could really have a huge advantage in right we didn't so custom became a swear word in our company right you could only be configurable we wanted to be easy for people to use I mean we wanted to have”
Watch at 04:21

Solve a capital-gains constraint

“this is the harder part this part sucked right I had 29 people I had to fire everyone down to six two of them in the back of the room with us still right now to this day um but that was a tough part thank God we were bootstrapped um because my father and I we were able to find a loophole in the IRS which I'm going to show you some artifacts on how we did that and I think that and then we had a pandemic we were able to the pandemic is part of our Survival Story which I'm also going to show you in a second but I think what's really cool here is that you know sometimes I think that as a”
Watch at 07:44

Learn from the community

“they they SBA looked at that was that okay they counted us for the 2018-2019 time when we had a lot of employees so we were able to get a ton of free money a little bit of debt I put in another 500 our shareholders put in another 275 and now we're to the to the point where we've got about an 880k shortfall between now and the next 12 months and we're going to bridge that through shareholder Milestones so um and as you can see here our burn rate it's it's going to be close to about 4 million dollars and we're going to see”
Watch at 10:37

Evaluate founder products

“simplify something that's super complex right we came from a world where it was super manual a lot of time a lot of effort and and and a lot of times he would follow you'd fall short so um really being able to to kind of to come through all of that you know we talk about and I think in my takeaway you know we talk about pivoting and I think that the most important thing is that you're never going to be scared to Pivot um you don't always have to Pivot right it may be like right now we're not”
Watch at 13:31

Got us to this amazing opportunity

“Got us to this amazing opportunity”
Read slide 2

Big Industry, Big Data, No Tech

“Big Industry, Big Data, No Tech.”
Read slide 5

Hard to Break a Service Mindset

“Hard to Break a Service Mindset”
Read slide 8

How We Made Our Pivot to SaaS

“How We Made Our Pivot to SaaS”
Read slide 12

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Resource files

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  • How being bootstrapped saved us - Slide Deck

About the speaker
Jonathan Fishbeck

Jonathan Fishbeck

Founder & CEO · EstateSpace

LinkedIn

CEO and Founder of EstateSpace. 3x Founder.

Company revenue
$2.7M
Team size
18

More founder interviews

Slide by slide

Each slide with a short explanation of what it shows. Open the slide text for its exact wording.

16 passages

The EstateSpace pivot

  1. Slide 1Open deck
    Slide text

    Jonathan Fishbeck CEO of Estatespace Founder500, Sept 2022 How being bootstrapped saved us … how service provided the spark to a blue ocean opportunity that lead to a $1m SaaS pivot and why we did it

  2. Slide 2Open deck

    The talk follows what, how, and why

    The story moves from finding and understanding an opportunity, through a SaaS pivot and debt conversion, to the reasons the company kept going. It also previews the near loss of focus and the role of service in shaping the business.

    Slide text

    Over the next 20 minutes: Got us to this amazing opportunity I’m going to show you our WHAT HOW WHY We did to better understand it Caused us to lose focus, almost fail We made our move to SaaS We converted $4.38M debt to 8.5% equity We thrived in a pandemic Our passion to serve, served us well What we knew all along came to fruition SaaS is the best thing on earth.

  3. Slide 3Open deck

    Revenue accelerates after the pivot

    The chart shows annual recurring revenue rising from $0 in 2017 to $4.7m in 2024, with faster growth after 2021. The labeled values are $50k in 2018, $150k in 2019 and 2020, $500k in 2021, $1.1m in 2022, and $1.8m in 2023.

    Slide text

    EstateSpace Revenue Growth

Understanding the problem

  1. Slide 4Open deck

    Section one: finding the opportunity

    This section traces how living the problem revealed an opportunity, why serving customers required scale, and how trying to make the transition became difficult.

    Slide text

    Let’s start with Section 1 Got us to this amazing opportunity “We lived the problem.” I’m going to show you WHAT WHAT WHAT We did to better understand it “To serve we needed scale.” Caused us to lose focus, almost fail “This was the hard part.”

  2. Slide 5Open deck

    A construction business saw a tech gap

    The company began in a large, data-heavy construction industry with little technology, then moved from a construction firm to SaaS. Photos of a project site and an on-site conversation ground the business story in construction work.

    Slide text

    Big Industry, Big Data, No Tech. From $15M ARR construction firm to SaaS

  3. Slide 6Open deck

    A growing market created room to build

    The chart argues that the U.S. market expanded from 500k users in 2000 to 5M in 2020, with 1M+ more expected within four years. Its curve continues toward 6M users by 2024 and names UHNWIs, family offices, and the luxury marketplace as the customer context.

    Slide text

    U.S. Market Growth 10X 500k in 2000 to 5M in 2020 - 1M+ in 4 years

  4. Slide 7Open deck

    Product completeness can distinguish leaders

    The positioning chart compares competitors on price and product completeness, placing EstateSpace in the high-price, more-complete quadrant. Other named products occupy less complete positions, underscoring the difficulty of building a clear technology leader.

    Slide text

    Why No Clear Technology Leader? …not an easy problem to solve!

The limits of a service mindset

  1. Slide 8Open deck

    Service habits do not transfer to SaaS

    The company struggled to turn service success into a repeatable product, with no customers, a beta-less product, and $0.00 in revenue. The three columns connect these gaps to trying too many things at once and losing focus while chasing revenue.

    Slide text

    Hard to Break a Service Mindset ZERO “Trying to do too much to fast and no one thing worked.” I’m going to show you how success doesn’t just transfer CUSTOMERS PRODUCT REVENUE BETA-LESS “Because we were chasing revenue, we got lost.” $0.00 “We were bleeding family money, but everything is about to change.”

  2. Slide 9Open deck

    Validate demand before defining the product

    The slide recommends speaking with people, surveying the market, and studying segments before choosing a target. It pairs market validation with a purpose-built, inclusive SaaS product and a clearly defined bullseye.

    Slide text

    We Know the Problem, We Have Demand Speak to people Survey the market Study key segments Fast growth market We’re not alone Be purpose built Inclusive SaaS Define our bullseye

Moving to SaaS

  1. Slide 10Open deck

    Section two: making the pivot

    This section covers the move to SaaS, converting debt to equity, and operating through a pandemic. Bootstrapping is presented as central to the pivot and survival.

    Slide text

    Let’s jump in to Section 2 We made our move to SaaS “This was the harder part!” I’m going to show you our pivot HOW HOW HOW We converted debt to equity “Thank God for bootstrapping.” We thrived in a pandemic “How a pandemic saved us.”

  2. Slide 11Open deck

    Debt converted into equity

    The slide presents converting $4.38M in debt into 8.5% equity as a turning point in the company’s story. A legal agreement appears beside the revenue chart to illustrate the financing change.

    Slide text

    EstateSpace Revenue Growth $4.38M in Debt to 8.5% Equity How being bootstrapped as a family saved us! 2019

  3. Slide 12Open deck

    The SaaS pivot involved a legal restructuring

    The slide pairs a member consent document changing the company name with a legal analysis of whether advances could be treated as equity rather than debt. It highlights that the original advances supported working capital and depended on the company developing a commercially valuable product.

    Slide text

    How We Made Our Pivot to SaaS

  4. Slide 13Open deck

    Bootstrapping funded a changing capital mix

    The diagram combines service revenue converted to equity with founder, shareholder, SBA, and pandemic funding as the company remained bootstrapped. The adjacent chart projects ARR rising above burn by 2025, while the labeled burn headline is $3.9M.

    Slide text

    How We Stayed Bootstrapped

Staying lean and bootstrapped

  1. Slide 14Open deck

    Stay lean and keep control

    The closing advice is to reduce weight, find product-market fit, own the business, and build a supportive peer network. A product screenshot reinforces the focus on lean operating habits and a simple task list.

    Slide text

    Stay Lean, Stay Bootstrapped… Less you weigh, the faster you go. Find your PMF and get traction Own YOUR business, don’t let it own you Keep alike network, stronger together

  2. Slide 15Open deck

    Service and focus carried the story

    The recap links the original opportunity and its near failure to the SaaS move, debt conversion, and survival through a pandemic. It closes by returning to service, what the team believed from the start, and its conviction in SaaS.

    Slide text

    Over the last 20 minutes Got us to this amazing opportunity WHAT HOW WHY We did to better understand it Caused us to lose focus, almost fail We made our move to SaaS We converted debt to equity We thrived in a pandemic Our passion to service, helped best serve us What we knew all along came to fruition SaaS is the best thing on earth. I showed you

  3. Slide 16Open deck

    Thank you from Jonathan Fishbeck

    Jonathan Fishbeck closes the presentation with a thank-you and his role at EstateSpace. The final card leaves the audience with the speaker and company identity.

    Slide text

    September 2022 Jonathan Fishbeck CEO of EstateSpace